Daphniphyllum calycinum is a shrubby plant found in northern Vietnam and Southeastern China. It is part of the Daphniphyllaceae family and is used in biodiesel, lubrication, soap-making, and Chinese medicine. It was first described by George Bentham in 1861 and is distinguished by its obovate-elliptic leaf blades and glaucous fruit. It is found in forests and thickets at altitudes of 100-700m and is commonly dispersed by birds. The plant is also used as a host by the sac-fungi Mycosphaerella fasciculata. While it has a wide distribution and large population, it is still of conservation concern due to the decline in its habitat. It is known by various names in different regions and has been used for its oil and medicinal properties.

Synonyms Top

Scientific name	Authority	First published in
Daphniphyllum calleryanum	Baill.	Étude Euphorb. : 565 (1858)
Daphniphyllum gaudichaudianum	Baill.	Étude Euphorb. : 565 (1858)

Common names Top

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Language	Common/alternative name
Chinese	牛耳枫
Chinese	牛耳枫子
Chinese	牛耳枫枝叶
Chinese	牛耳枫根
Chinese	南岭虎皮楠
Chinese	牛耳楓

Subspecies (abbr. subsp./ssp.) Top

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Varieties (abbr. var.) Top

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Subvarieties (abbr. subvar.) Top

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Forms (abbr. f.) Top

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Germination/Propagation Top

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No germination or propagation data was added yet.

Distribution (via POWO/KEW) Top

Legend for the distribution data:

- Doubtful data

- Extinct

- Introduced

- Native

Asia-temperate click to expand
- China
  - China Southeast

Asia-tropical click to expand
- Indo-China
  - Vietnam

Links to other databases Top

Suggest others/fix!

Database	ID/link to page
World Flora Online	wfo-0000937684
Tropicos	10100032
KEW	urn:lsid:ipni.org:names:344216-1
The Plant List	kew-56350
Open Tree Of Life	816930
Observations.org	433709
NCBI Taxonomy	182071
IUCN Red List	147379344
IPNI	344216-1
iNaturalist	415460
GBIF	4261959
EOL	2888690
Elurikkus	491996
Wikipedia	Daphniphyllum_calycinum
CMAUP	NPO21139

Genomes (via NCBI) Top

No reference genome is available on NCBI yet. We are constantly monitoring for new data.

Scientific Literature Top

Below are displayed the latest 15 articles published in PMC (PubMed Central®) and other sources (DOI number only)!
If you wish to see all the related articles click here.

Title

Authors

Publication

Released

IDs

Finding activity through rigidity: syntheses of natural products containing tricyclic bridgehead carbon centers

Xu Z, Li X, Rose JA, Herzon SB

Nat Prod Rep

16-Aug-2023

PMCID:	PMC10472132
doi:	10.1039/d3np00008g
PMID:	37140079

Density Functional Theory Calculations and Molecular Docking Analyses of Flavonoids for Their Possible Application against the Acetylcholinesterase and Triose-Phosphate Isomerase Proteins of Rhipicephalus microplus

Malak N, Alotaibi BS, Khan A, Khan A, Ullah S, Nasreen N, Niaz S, Chen CC

Molecules

20-Apr-2023

PMCID:	PMC10145301
doi:	10.3390/molecules28083606
PMID:	37110838

Advances in research on the effectiveness and mechanism of Traditional Chinese Medicine formulas for colitis-associated colorectal cancer

Wei X, Leng X, Li G, Wang R, Chi L, Sun D

Front Pharmacol

23-Feb-2023

PMCID:	PMC9995472
doi:	10.3389/fphar.2023.1120672
PMID:	36909166

Assessment of a Bionic Broach Implanted with Nylon Fibers

Ni J, Zhang H, Feng K, Zhao H

Materials (Basel)

17-Dec-2022

PMCID:	PMC9786619
doi:	10.3390/ma15249040
PMID:	36556850

Mitsunobu Reaction: A Powerful Tool for the Synthesis of Natural Products: A Review

Munawar S, Zahoor AF, Ali S, Javed S, Irfan M, Irfan A, Kotwica-Mojzych K, Mojzych M

Molecules

17-Oct-2022

PMCID:	PMC9609662
doi:	10.3390/molecules27206953
PMID:	36296545

Photogrammetric reconstruction of 3D carpological collection in high resolution for plants authentication and species discovery

Wang HL, Wong TH, Chan YM, Cheng YS, Lau DT

PLoS One

04-Aug-2022

PMCID:	PMC9352034
doi:	10.1371/journal.pone.0270199
PMID:	35925934

Phytolith Assemblages as a Promising Tool for Quantitative Canopy Coverage Reconstruction in Subtropical Forests, China

Li N, Yu F, Sack D, Huang Z, Tian G, Liu S

Front Plant Sci

20-Jun-2022

PMCID:	PMC9251495
doi:	10.3389/fpls.2022.912627
PMID:	35795347

Calycindaphines A–J, Daphniphyllum alkaloids from the roots of Daphniphyllum calycinum

Yang J, Liu X, Fu J, Lyu HY, Bai LP, Jiang ZH, Zhu GY

RSC Adv

01-Mar-2021

PMCID:	PMC8695325
doi:	10.1039/d1ra00107h
PMID:	35423413

Feng-Liao-Chang-Wei-Kang Combined with 5-Fluorouracil Synergistically Suppresses Colitis-Associated Colorectal Cancer via the IL-6/STAT3 Signalling Pathway

Zhong L, Yang F, Gan L, Yang Z, Tian S, Huang M, Lv C, Huang L

Evid Based Complement Alternat Med

03-Oct-2020

PMCID:	PMC7556056
doi:	10.1155/2020/1395954
PMID:	33082817

Photosynthesis Performance and Antioxidative Enzymes Response of Melia azedarach and Ligustrum lucidum Plants Under Pb–Zn Mine Tailing Conditions

Huang X, Zhu F, He Z, Chen X, Wang G, Liu M, Xu H

Front Plant Sci

15-Sep-2020

PMCID:	PMC7522552
doi:	10.3389/fpls.2020.571157
PMID:	33042188

FengLiao affects gut microbiota and the expression levels of Na+/H+ exchangers, aquaporins and acute phase proteins in mice with castor oil-induced diarrhea

Chen W, Peng X, Yu J, Chen X, Yuan M, Xiang R, He L, Yu D, Kang H, Pan Y, Xu Z

PLoS One

28-Jul-2020

PMCID:	PMC7386626
doi:	10.1371/journal.pone.0236511
PMID:	32722717

Effects of Fengliao-Changweikang in Diarrhea-predominant Irritable Bowel Syndrome Rats and Its Mechanism Involving Colonic Motility

Jia M, Lu X, Wang Z, Zhao L, Zhang S

J Neurogastroenterol Motil

01-Jul-2018

PMCID:	PMC6034674
doi:	10.5056/jnm17093
PMID:	29715711

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbons

Büschleb M, Dorich S, Hanessian S, Tao D, Schenthal KB, Overman LE

Angew Chem Int Ed Engl

02-Feb-2016

PMCID:	PMC4865016
doi:	10.1002/anie.201507549
PMID:	26836448

The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N

Shvartsbart A, Smith AB III

J Am Chem Soc

10-Mar-2015

PMCID:	PMC4394112
doi:	10.1021/ja503899t
PMID:	25756504

Deoxycalyciphylline B, a Hepatotoxic Alkaloid from Daphniphyllum calycinum

Zhang X, Zhang J, Tan Y, Liu Q, Liu M

Molecules

13-Aug-2012

PMCID:	PMC6268957
doi:	10.3390/molecules17089641
PMID:	22890169

Phytochemical Profile Top

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Below are displayed the proven (via scientific papers) natural compounds!
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Name	PubChem ID	Canonical SMILES	MW	Found in	Proof
> Alkaloids and derivatives / Daphniphylline-type alkaloids
(1S,2R,3S,7R,10S,11S,13S,14R)-2-[(3S)-3-[(1R,4S,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-hydroxypropyl]-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-11-ol	163105059	Click to see CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3O)CCC(C6(COC7(CCC6O7)C)C)O)C	487.70	unknown	https://doi.org/10.1021/NP800515S
(1S,2R,3S,7R,11S,13S,14R)-2-[(3S)-3-[(1R,4S,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-hydroxypropyl]-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-11-ol	163193382	Click to see CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3O)CCC(C6(COC7(CCC6O7)C)C)O)C	487.70	unknown	https://doi.org/10.1021/NP800515S
(2S)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-3-[(1S,2R,3S,7R,10S,13S,14R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]propan-1-one	101391555	Click to see CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3)CC(C(=O)C6(COC7(CCC6O7)C)C)O)C	485.70	unknown	https://doi.org/10.1021/NP060088F
1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3R,7R,10S,14R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]propan-1-one	102060135	Click to see CC(C)C1CCC2(C3CCC45C3NC1C2(C4CCC5)CCC(=O)C6(COC7(CCC6O7)C)C)C	469.70	unknown	https://doi.org/10.1021/NP060088F
1-[(1S,4S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(3R,7S,10R,13R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]propan-1-one	138113965	Click to see CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3)CCC(=O)C6(COC7(CCC6O7)C)C)C	469.70	unknown	https://doi.org/10.1021/NP060088F
2-[3-(1,4-Dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl)-3-hydroxypropyl]-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-11-ol	74429785	Click to see CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3O)CCC(C6(COC7(CCC6O7)C)C)O)C	487.70	unknown	https://doi.org/10.1021/NP800515S
3-[(1S,2R,7R,10S,14R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]propanoic acid	102245576	Click to see CC(C)C1CCC2(C3CCC45C3NC1C2(C4CCC5)CCC(=O)O)C	345.50	unknown	https://doi.org/10.1021/NP060088F
Methyl 3-(11-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl)propanoate	162916244	Click to see CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3O)CCC(=O)OC)C	375.50	unknown	https://doi.org/10.1002/HLCA.200900383
methyl 3-[(1R,2S,3R,7S,10R,11R,13R,14S)-11-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]propanoate	162916245	Click to see CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3O)CCC(=O)OC)C	375.50	unknown	https://doi.org/10.1002/HLCA.200900383
methyl 3-[(1S,2R,3R,7R,9S,10S,11R,13S,14R)-9-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]propanoate	25209368	Click to see CC(C)C1CCC2(C3C(CC45C3NC1C2(C4CCC5)CCC(=O)OC)O)C	375.50	unknown	https://doi.org/10.1021/NP800515S
methyl 3-[(1S,2R,3R,7R,9S,14R)-9-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]propanoate	102282915	Click to see CC(C)C1CCC2(C3C(CC45C3NC1C2(C4CCC5)CCC(=O)OC)O)C	375.50	unknown	https://doi.org/10.1021/NP800515S
methyl 3-[(1S,2R,3S,7R,10S,13S,14R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]propanoate	102058172	Click to see CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3)CCC(=O)OC)C	359.50	unknown	https://doi.org/10.1021/NP060088F
methyl 3-[(1S,2R,3S,7S,8S,10S,13S,14R)-8-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]propanoate	25135569	Click to see CC(C)C1CCC2(C3CC(C45CCCC4C2(C1N5C3)CCC(=O)OC)O)C	375.50	unknown	https://doi.org/10.1021/NP060088F
> Alkaloids and derivatives / Yuzurimine-type alkaloids
(1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(1R,2S,3R,5R,6S,10S,16R,17R)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icos-13(19)-ene-17-carbonyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	21580235	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C2CC1C6=O)C)C(=O)OCC7C(C(C(C(O7)OC8C9C(CC=C9CO)C(=CO8)C(=O)O)O)O)O	711.80	unknown	https://doi.org/10.1021/NP040038F
(1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(1R,2S,3R,5S,6S,10S,16R,17R)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icos-13(19)-ene-17-carbonyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	162918976	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C2CC1C6=O)C)C(=O)OCC7C(C(C(C(O7)OC8C9C(CC=C9CO)C(=CO8)C(=O)O)O)O)O	711.80	unknown	https://doi.org/10.1021/NP040038F
(4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2S,5S,6S,10S,16R,17R)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icos-13(19)-ene-17-carbonyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	102074149	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C2CC1C6=O)C)C(=O)OCC7C(C(C(C(O7)OC8C9C(CC=C9CO)C(=CO8)C(=O)O)O)O)O	711.80	unknown	via CMAUP database
1-[6-[(2,6-Dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icos-13(19)-ene-17-carbonyl)oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	73804414	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C2CC1C6=O)C)C(=O)OCC7C(C(C(C(O7)OC8C9C(CC=C9CO)C(=CO8)C(=O)O)O)O)O	711.80	unknown	https://doi.org/10.1021/NP040038F
Daphniyunnine A	76763789	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C2CC1C6=O)C)C(=O)OC	369.50	unknown	https://doi.org/10.1002/HLCA.200900027
methyl (1R,2S,3R,5R,10S,16R)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icos-13(19)-ene-17-carboxylate	138114016	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C2CC1C6=O)C)C(=O)OC	369.50	unknown	https://doi.org/10.1021/NP060088F
methyl (1R,2S,3R,5R,10S)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icosa-13(19),16-diene-17-carboxylate	138114021	Click to see CC1CN2CC3CCC4=C5C(=C(CC56C3(C2CC1C6=O)C)C(=O)OC)CC4	367.50	unknown	https://doi.org/10.1021/NP060088F
Methyl 2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icos-13(19)-ene-17-carboxylate	72994110	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C2CC1C6=O)C)C(=O)OC	369.50	unknown	https://doi.org/10.1002/HLCA.200900027
> Hydrocarbons / Unsaturated hydrocarbons / Olefins / Cyclic olefins / Azulenes
(12S,16S,17R,19R,20S)-22-hydroxy-16,20-dimethyl-4-oxa-14-azahexacyclo[15.4.1.02,7.08,21.012,20.014,19]docosa-1(22),2(7),8(21)-triene-3,9-dione	54720923	Click to see CC1CN2CC3CCC(=O)C4=C5C3(C2CC1C(=C5C6=C4CCOC6=O)O)C	367.40	unknown	https://doi.org/10.1021/NP060088F
methyl (2S,3R,5R,10S)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.15,19.02,10.03,8.017,20]henicosa-1(19),13(20),17-triene-18-carboxylate	138114028	Click to see CC1CN2CC3CCC4=C5C(=C(C6=C5C3(C2CC1C6=O)C)C(=O)OC)CCO4	381.50	unknown	https://doi.org/10.1021/NP060088F
> Lipids and lipid-like molecules / Prenol lipids / Diterpenoids / Kaurane diterpenoids
(1R,2S,3S,5S,7R,8S,9S,10S,11R,12R)-12-(hydroxymethyl)-12-methyl-6-methylidene-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecane-3,7,9,10-tetrol	102298137	Click to see CC1(CCCC23C1C(C(C45C2C(CC(C4)C(=C)C5O)O)(OC3)O)O)CO	366.40	unknown	via CMAUP database
(1S,2S,5S,7R,8S,9S,10S,11R,12R)-7,9,10-trihydroxy-12-(hydroxymethyl)-12-methyl-6-methylidene-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadec-14-en-3-one	102298136	Click to see CC1(CC=CC23C1C(C(C45C2C(=O)CC(C4)C(=C)C5O)(OC3)O)O)CO	362.40	unknown	via CMAUP database
1alpha,6beta,7beta,11alpha,15beta-Pentahydroxy-7alpha,20-epoxy-ent-kaur-16-ene	101677459	Click to see CC1(CCC(C23C1C(C(C45C2C(CC(C4)C(=C)C5O)O)(OC3)O)O)O)C	366.40	unknown	via CMAUP database
Kaurane-7beta,16,17-triol	101676167	Click to see CC1(CCCC2(C1CC(C34C2CCC(C3)C(C4)(CO)O)O)C)C	322.50	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Sesquiterpenoids
1-(1,4-Dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl)-3-(1-methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl)propan-1-one	162863657	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)C6(COC7(CCC6O7)C)C)C	455.70	unknown	https://doi.org/10.1021/OL0631455
1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1R,2R,3R,7S,10S,12S,13R)-1-methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl]propan-1-one	102275335	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)C6(COC7(CCC6O7)C)C)C	455.70	unknown	https://doi.org/10.1021/NP060088F
1-[(1S,4S,5R)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2S,3R,7S,10R,12R,13S)-1-methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl]propan-1-one	163186440	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)C6(COC7(CCC6O7)C)C)C	455.70	unknown	https://doi.org/10.1021/OL0631455
3-(1-Methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl)propanoic acid	74392273	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)O)C	331.50	unknown	https://doi.org/10.1021/NP800323M
3-(11-Methyl-17-propan-2-yl-14-oxa-16-azapentacyclo[11.3.1.02,11.03,7.010,15]heptadec-3-en-2-yl)propanoic acid	162939288	Click to see CC(C)C1C2CC3(C4CCC5CCC=C5C3(C1NC4O2)CCC(=O)O)C	359.50	unknown	https://doi.org/10.1021/OL9019919
3-[(1R,2R,3S,10S,12S,13R)-1-methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl]propanoic acid	102596800	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)O)C	331.50	unknown	https://doi.org/10.1021/NP060088F
3-[(1R,2R,3S,7R,10S,12S,13R)-1-methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl]propanoic acid	163032778	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)O)C	331.50	unknown	https://doi.org/10.1021/NP800323M
3-[(1R,2R,7S,10R,11R,13R,15S,17R)-11-methyl-17-propan-2-yl-14-oxa-16-azapentacyclo[11.3.1.02,11.03,7.010,15]heptadec-3-en-2-yl]propanoic acid	162939289	Click to see CC(C)C1C2CC3(C4CCC5CCC=C5C3(C1NC4O2)CCC(=O)O)C	359.50	unknown	https://doi.org/10.1021/OL9019919
3-[(1S,2S,7R,10S,13S,14R)-1-methyl-14-propan-2-yl-12-azatetracyclo[8.6.0.02,13.03,7]hexadeca-3,11-dien-2-yl]propanoic acid	102245575	Click to see CC(C)C1CCC2(C3CCC4CCC=C4C2(C1N=C3)CCC(=O)O)C	343.50	unknown	https://doi.org/10.1021/NP060088F
7-Megastigmene-3,5,6,9-tetraol	637237	Click to see CC(C=CC1(C(CC(CC1(C)O)O)(C)C)O)O	244.33	unknown	via CMAUP database
methyl (1S,2S,4S,5R,6S,9S,15R,16R)-4-hydroxy-2-methyl-5-propan-2-yl-7-azapentacyclo[10.5.1.01,6.02,9.015,18]octadec-12(18)-ene-16-carboxylate	25135429	Click to see CC(C)C1C(CC2(C3CCC4=C5C2(C1NC3)CC(C5CC4)C(=O)OC)C)O	373.50	unknown	https://doi.org/10.1021/NP800323M
methyl (1S,2S,4S,5R,6S,9S)-4-hydroxy-2-methyl-5-propan-2-yl-7-azapentacyclo[10.5.1.01,6.02,9.015,18]octadec-12(18)-ene-16-carboxylate	102596798	Click to see CC(C)C1C(CC2(C3CCC4=C5C2(C1NC3)CC(C5CC4)C(=O)OC)C)O	373.50	unknown	https://doi.org/10.1021/NP060088F
methyl (1S,2S,5R,6S,9S,15S,16S)-2-methyl-5-propan-2-yl-7-azapentacyclo[10.5.1.01,6.02,9.015,18]octadec-12(18)-ene-16-carboxylate	101776473	Click to see CC(C)C1CCC2(C3CCC4=C5C2(C1NC3)CC(C5CC4)C(=O)OC)C	357.50	unknown	https://doi.org/10.1016/J.TET.2005.03.146 https://doi.org/10.1021/NP060088F
Methyl 2-methyl-5-propan-2-yl-7-azapentacyclo[10.5.1.01,6.02,9.015,18]octadec-12(18)-ene-16-carboxylate	73796628	Click to see CC(C)C1CCC2(C3CCC4=C5C2(C1NC3)CC(C5CC4)C(=O)OC)C	357.50	unknown	https://doi.org/10.1016/J.TET.2005.03.146
Methyl 3-(1-methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl)propanoate	163023838	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)OC)C	345.50	unknown	https://doi.org/10.1016/J.TETLET.2007.03.156
Methyl 3-(1-methyl-14-propan-2-yl-12-azatetracyclo[8.6.0.02,13.03,7]hexadec-3-en-2-yl)propanoate	162915703	Click to see CC(C)C1CCC2(C3CCC4CCC=C4C2(C1NC3)CCC(=O)OC)C	359.50	unknown	https://doi.org/10.1016/J.TET.2007.11.087
Methyl 3-(15-hydroxy-1-methyl-14-propan-2-yl-12-azatetracyclo[8.6.0.02,13.03,7]hexadec-3-en-2-yl)propanoate	74392194	Click to see CC(C)C1C(CC2(C3CCC4CCC=C4C2(C1NC3)CCC(=O)OC)C)O	375.50	unknown	https://doi.org/10.1021/NP800323M
methyl 3-[(1R,2R,3S,10S,12S,13R)-1-methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl]propanoate	102076506	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)OC)C	345.50	unknown	https://doi.org/10.1021/NP060088F
methyl 3-[(1S,2R,7R,10S,13R,14R)-1-methyl-14-propan-2-yl-12-azatetracyclo[8.6.0.02,13.03,7]hexadec-3-en-2-yl]propanoate	101839809	Click to see CC(C)C1CCC2(C3CCC4CCC=C4C2(C1NC3)CCC(=O)OC)C	359.50	unknown	https://doi.org/10.1021/NP060088F
methyl 3-[(1S,2R,7R)-7-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,8.07,12]hexadecan-2-yl]propanoate	129317132	Click to see CC(C)C1CCC2(C3CC4C5C2(C1N(C3)C4(CCC5)O)CCC(=O)OC)C	375.50	unknown	https://doi.org/10.1021/NP060088F
methyl 3-[(1S,2S,3R,7S,10R,12R,13S)-1-methyl-13-propan-2-yl-11-azapentacyclo[8.5.0.02,12.03,7.07,11]pentadecan-2-yl]propanoate	163023839	Click to see CC(C)C1CCC2(C3CCC45N3C1C2(C4CCC5)CCC(=O)OC)C	345.50	unknown	https://doi.org/10.1016/J.TETLET.2007.03.156
methyl 3-[(1S,2S,7R,10S,13S,14R,15S)-15-hydroxy-1-methyl-14-propan-2-yl-12-azatetracyclo[8.6.0.02,13.03,7]hexadec-3-en-2-yl]propanoate	25135567	Click to see CC(C)C1C(CC2(C3CCC4CCC=C4C2(C1NC3)CCC(=O)OC)C)O	375.50	unknown	https://doi.org/10.1021/NP800323M
methyl 3-[(1S,2S,7R,10S,13S,14R)-1-methyl-14-propan-2-yl-12-azatetracyclo[8.6.0.02,13.03,7]hexadec-3-en-2-yl]propanoate	162915704	Click to see CC(C)C1CCC2(C3CCC4CCC=C4C2(C1NC3)CCC(=O)OC)C	359.50	unknown	https://doi.org/10.1016/J.TET.2007.11.087
methyl 3-[(1S,2S,7S,10S,13S,14R,15S)-15-hydroxy-1-methyl-14-propan-2-yl-12-azatetracyclo[8.6.0.02,13.03,7]hexadec-3-en-2-yl]propanoate	102596799	Click to see CC(C)C1C(CC2(C3CCC4CCC=C4C2(C1NC3)CCC(=O)OC)C)O	375.50	unknown	https://doi.org/10.1021/NP060088F
Methyl 4-hydroxy-2-methyl-5-propan-2-yl-7-azapentacyclo[10.5.1.01,6.02,9.015,18]octadec-12(18)-ene-16-carboxylate	74392113	Click to see CC(C)C1C(CC2(C3CCC4=C5C2(C1NC3)CC(C5CC4)C(=O)OC)C)O	373.50	unknown	https://doi.org/10.1021/NP800323M
> Lipids and lipid-like molecules / Prenol lipids / Terpene glycosides / Iridoid O-glycosides
(1R,4aR,7aR)-7-(hydroxymethyl)-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(1S,2'R,5R,11S,12S,15S)-2'-methoxy-3-methyl-2'-propan-2-ylspiro[3-azatetracyclo[6.5.1.11,5.011,14]pentadec-8(14)-ene-15,5'-oxane]-12-carbonyl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	163048457	Click to see CC(C)C1(CCC2(CO1)C3CCC4=C5C2(CC(C5CC4)C(=O)OCC6C(C(C(C(O6)OC7C8C(CC=C8CO)C(=CO7)C(=O)O)O)O)O)CN(C3)C)OC	759.90	unknown	https://doi.org/10.1016/J.TETLET.2003.11.005
(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(1R,2'R,5S,11R,12R,15S)-2'-hydroxy-3-methyl-2'-propan-2-ylspiro[3-azatetracyclo[6.5.1.11,5.011,14]pentadec-8(14)-ene-15,5'-oxane]-12-carbonyl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	163040395	Click to see CC(C)C1(CCC2(CO1)C3CCC4=C5C2(CC(C5CC4)C(=O)OCC6C(C(C(C(O6)OC7C8C(CC=C8CO)C(=CO7)C(=O)O)O)O)O)CN(C3)C)O	745.90	unknown	https://doi.org/10.1016/J.TET.2005.03.146
(1S,4aS)-1-[6-[[(3R,4R,7R,10S,11S,14R,15S,20R,21S)-11,15-dimethyl-19-oxa-17-azaheptacyclo[12.6.1.01,11.04,20.07,20.010,18.017,21]henicosane-3-carbonyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	102353852	Click to see CC1CN2C3C1CCC4(C35CC(C6C57C(CC6)CCC4C2O7)C(=O)OCC8C(C(C(C(O8)OC9C1C(CC=C1CO)C(=CO9)C(=O)O)O)O)O)C	713.80	unknown	https://doi.org/10.1002/CHIN.200416174
7-(Hydroxymethyl)-1-[3,4,5-trihydroxy-6-[(2'-hydroxy-3-methyl-2'-propan-2-ylspiro[3-azatetracyclo[6.5.1.11,5.011,14]pentadec-8(14)-ene-15,5'-oxane]-12-carbonyl)oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	163040394	Click to see CC(C)C1(CCC2(CO1)C3CCC4=C5C2(CC(C5CC4)C(=O)OCC6C(C(C(C(O6)OC7C8C(CC=C8CO)C(=CO7)C(=O)O)O)O)O)CN(C3)C)O	745.90	unknown	https://doi.org/10.1016/J.TET.2005.03.146
7-(Hydroxymethyl)-1-[3,4,5-trihydroxy-6-[(2'-methoxy-3-methyl-2'-propan-2-ylspiro[3-azatetracyclo[6.5.1.11,5.011,14]pentadec-8(14)-ene-15,5'-oxane]-12-carbonyl)oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid	163048456	Click to see CC(C)C1(CCC2(CO1)C3CCC4=C5C2(CC(C5CC4)C(=O)OCC6C(C(C(C(O6)OC7C8C(CC=C8CO)C(=CO7)C(=O)O)O)O)O)CN(C3)C)OC	759.90	unknown	https://doi.org/10.1002/CHIN.200416174 https://doi.org/10.1016/J.TETLET.2003.11.005
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones / Diterpene lactones
(1R,3E,5S,9R,12E)-3,12-dimethyl-8-methylidene-6,18-dioxatricyclo[14.2.1.05,9]nonadeca-3,12,16(19)-triene-7,17-dione	6451060	Click to see CC1=CCCC2=CC(CC(=CC3C(CC1)C(=C)C(=O)O3)C)OC2=O	328.40	unknown	via CMAUP database
(1S,2'R,5R,6S,9R,10S)-2'-(hydroxymethyl)-10-(methoxymethyl)-3',3'-dimethylspiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,1'-cyclohexane]-2,11-dione	49870970	Click to see CC1(CCCC2(C1CO)COC(=O)C34C2CCC(C3)C(C4=O)COC)C	364.50	unknown	via CMAUP database
(1S,2'R,5R,6S,9R)-2'-(hydroxymethyl)-3',3'-dimethyl-10-methylidenespiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,1'-cyclohexane]-2,11-dione	49870969	Click to see CC1(CCCC2(C1CO)COC(=O)C34C2CCC(C3)C(=C)C4=O)C	332.40	unknown	via CMAUP database
(1S,2S,3R,5R,7R,8S,11S,14R,17S,20R)-3,5,7-trihydroxy-14-methyl-6-methylidene-10,16,18-trioxahexacyclo[12.5.1.15,8.01,11.02,8.017,20]henicosan-9-one	72947649	Click to see CC12CCC3C4(C1C(OC2)OC4)C5C(CC6(CC5(C(C6=C)O)C(=O)O3)O)O	378.40	unknown	via CMAUP database
(1S,2S,3R,5S,7R,8S,11S,14R,17S,20R)-3,7-dihydroxy-14-methyl-6-methylidene-10,16,18-trioxahexacyclo[12.5.1.15,8.01,11.02,8.017,20]henicosan-9-one	20056294	Click to see CC12CCC3C4(C1C(OC2)OC4)C5C(CC6CC5(C(C6=C)O)C(=O)O3)O	362.40	unknown	via CMAUP database
(1S,4S,6R,8R,9R,12S,13S,14R,16S,17S)-6,9,14,17-tetrahydroxy-7,7,17-trimethyl-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecane-2,18-dione	72947650	Click to see CC1(C(CC2C3(C1C(OC3)O)C4C(CC5CC4(C(=O)C5(C)O)C(=O)O2)O)O)C	396.40	unknown	via CMAUP database
(1S,4S,8R,9R,12S,13S,14S,16R,17R,19R)-9,19-dihydroxy-7,7-dimethyl-18-methylidene-3,10,15-trioxahexacyclo[15.2.1.01,13.04,12.08,12.014,16]icosan-2-one	72947453	Click to see CC1(CCC2C3(C1C(OC3)O)C4C5C(O5)C6CC4(C(C6=C)O)C(=O)O2)C	362.40	unknown	via CMAUP database
(1S,4S,8R,9R,12S,13S,14S,16S,17S,18S)-9,14,17,18-tetrahydroxy-7,7,17-trimethyl-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecan-2-one	72947651	Click to see CC1(CCC2C3(C1C(OC3)O)C4C(CC5CC4(C(C5(C)O)O)C(=O)O2)O)C	382.40	unknown	via CMAUP database
(1S,4S,8R,9R,12S,13S,16R,18R)-9,18-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecan-2-one	76309974	Click to see CC1(CCC2C3(C1C(OC3)O)C4CCC5CC4(C(C5=C)O)C(=O)O2)C	348.40	unknown	via CMAUP database
(1S,4S,8R,9R,12S,13S,16S,18R)-9,18-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadec-14-en-2-one	72947454	Click to see CC1(CCC2C3(C1C(OC3)O)C4C=CC5CC4(C(C5=C)O)C(=O)O2)C	346.40	unknown	via CMAUP database
(6R,9S,13R,16S)-1alpha,6,11alpha-Trihydroxy-15-oxo-6,20:12beta,17-diepoxy-6,7-secokaurane-7-oic acid 7,1-lactone	24764126	Click to see CC1(CCC2C3(C1C(OC3)O)C4C(C5C6CC4(C(=O)C6CO5)C(=O)O2)O)C	378.40	unknown	via CMAUP database
Enemin	352542	Click to see CC1(C(CC2C3(C1C(OC3)O)C4CCC5CC4(C(=O)C5=C)C(=O)O2)O)C	362.40	unknown	via CMAUP database
Epinodosin	9975896	Click to see CC1(CCC2C3(C1C(OC3)O)C4C(CC5CC4(C(=O)C5=C)C(=O)O2)O)C	362.40	unknown	via CMAUP database
Longirabdolide C	101670648	Click to see CC1(C(CC2C3(C1C(OC3)O)C4C(CC5CC4(C(=O)C5=C)C(=O)O2)O)O)C	378.40	unknown	via CMAUP database
Macrocalin A	11382408	Click to see CC1(CCC2C3(C1C(OC3)O)C4CCC5CC4(C(=O)C5=C)C(=O)O2)C	346.40	unknown	via CMAUP database
Maoyecrystal D	46883375	Click to see CC1(CCC2C3(C1C(OC3)O)C4C(CC5CC4(C(=O)C5CO)C(=O)O2)O)C	380.40	unknown	via CMAUP database
Nodosin	10248089	Click to see CC1(CCC2C3(C1C(OC3)O)C4C(CC5CC4(C(=O)C5=C)C(=O)O2)O)C	362.40	unknown	via CMAUP database
Sculponeatin A	15922655	Click to see CC12CCC3C4(C1C(OC2)OC4)C5C(CC6CC5(C(=O)C6=C)C(=O)O3)O	360.40	unknown	via CMAUP database
Sculponin F	44557721	Click to see CC(=O)OC1C(=C)C2CC(C3C1(C2)C(=O)OC4C35COC(C5C(C(C4)O)(C)C)O)O	422.50	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Triterpenoids
(1S,1'S,4S,4'S,6S,7'R,8R,9R,10'S,12S,13S,13'S,14'S,15'R,16R,17S,17'S,25'R)-6,9,15'-trihydroxy-7,7,7'-trimethylspiro[3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecane-17,21'-3,9,11,22-tetraoxaheptacyclo[15.6.1.17,10.01,14.04,13.018,23.013,25]pentacos-18(23)-ene]-2,2',18-trione	44557720	Click to see CC1(C(CC2C3(C1C(OC3)O)C4CCC5CC4(C(=O)C56CCC7=C(O6)C89CC7CC(C8C13COC4C1C(CCC3OC9=O)(CO4)C)O)C(=O)O2)O)C	722.80	unknown	via CMAUP database
[7-hydroxy-1,5-dimethyl-8-[2-[(3S,7S)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]ethyl]-6-oxabicyclo[3.2.1]octan-2-yl] acetate	133561803	Click to see CC(C)C1CCC2(C3CCC45C3NC1C2(C4CCC5)CCC6C7(CCC(C6(C(O7)O)C)OC(=O)C)C)C	513.80	unknown	https://doi.org/10.1021/NP060088F
Oleanolic Acid	10494	Click to see CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)C	456.70	unknown	via CMAUP database
Sculponin D	44557719	Click to see CC12CCC3C4(C1C(OC2)OC4)C5C(CC6CC5(C7=C6CCC8(O7)C9CC(C1C(C9)(C8=O)C(=O)OC2C11COC4C1C(CC2)(CO4)C)O)C(=O)O3)O	720.80	unknown	via CMAUP database
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Stigmastanes and derivatives
Beta-Sitosterol	222284	Click to see CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C	414.70	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Phenylalanine and derivatives
[(2S)-2-acetamido-3-phenylpropyl] (2S)-2-benzamido-3-phenylpropanoate	46222163	Click to see CC(=O)NC(CC1=CC=CC=C1)COC(=O)C(CC2=CC=CC=C2)NC(=O)C3=CC=CC=C3	444.50	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Amino acids and derivatives / Delta amino acids and derivatives
Paxdaphnine B	139071432	Click to see CCC12CCC3(C14CC(C5C4=C(CCC3CN2)CC5)C(=O)OC)CO.CCC12CCC3(C14CC(C5C4=C(CCC3CN2)CC5)C(=O)OC)CO	690.90	unknown	https://doi.org/10.1021/NP060088F
> Organic acids and derivatives / Carboxylic acids and derivatives / Dicarboxylic acids and derivatives
(E)-but-2-enedioate;hydron	21883788	Click to see [H+].[H+].C(=CC(=O)[O-])C(=O)[O-]	116.07	unknown	via CMAUP database
> Organoheterocyclic compounds / Azaspirodecane derivatives
(1R,3R,4R,10S,14S,15R,18R,19S)-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylic acid	21580234	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C2C1CCC63CO)C(=O)O	357.50	unknown	https://doi.org/10.1021/NP040038F
(1R,3R,4R,10S,14S,15R,18R,19S)-19-hydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylic acid	163190156	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(CCC1C62O)CO)C(=O)O	373.50	unknown	https://doi.org/10.1021/NP040038F
(1S,7S,10S,14S,15R,18S,19R)-7,19-dihydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-4(20)-en-3-one	163041068	Click to see CC1CN2CC3CCC4(CCC5=C4C6(C3(CCC1C62O)C)CC5=O)O	343.50	unknown	https://doi.org/10.1021/OL9019919
(3R,4R,10S,14S,19S)-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylic acid	163188038	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C2C1CCC63CO)C(=O)O	357.50	unknown	https://doi.org/10.1021/NP040038F
(4R,7R,10S,14R,15S,18R,20S,21S)-11,15-dimethyl-19-oxa-17-azaheptacyclo[12.6.1.01,11.04,20.07,20.010,18.017,21]henicosane-3-carboxylic acid	102353853	Click to see CC1CN2C3C1CCC4(C35CC(C6C57C(CC6)CCC4C2O7)C(=O)O)C	357.50	unknown	https://doi.org/10.1002/CHIN.200416174
19-Hydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylic acid	163072734	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(CCC1C62O)CO)C(=O)O	373.50	unknown	https://doi.org/10.1021/NP040038F
4-(6-Hydroxy-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl)butanoic acid	162970685	Click to see CC(C)C1CCC2C3CCC45C(C2(C1N4C3)CCCC(=O)O)CCC5O	361.50	unknown	https://doi.org/10.1021/NP040038F
4-[(1S,2S,3S,6R,7R,10S,13S,14R)-6-hydroxy-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]butanoic acid	162970686	Click to see CC(C)C1CCC2C3CCC45C(C2(C1N4C3)CCCC(=O)O)CCC5O	361.50	unknown	https://doi.org/10.1021/NP040038F
7,19-Dihydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-4(20)-en-3-one	163041067	Click to see CC1CN2CC3CCC4(CCC5=C4C6(C3(CCC1C62O)C)CC5=O)O	343.50	unknown	https://doi.org/10.1021/OL9019919
methyl (1R,10R,14S,15R,18R,19S)-19-hydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icosa-3,7(20)-diene-3-carboxylate	102154904	Click to see CC1CN2CC3CCC4=C5C(=C(CC56C3(CCC1C62O)C)C(=O)OC)CC4	369.50	unknown	https://doi.org/10.1021/NP060088F
methyl (1R,10R,15R,18S,19R)-17,19-dihydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icosa-3,7(20)-diene-3-carboxylate	102596794	Click to see CC1CN2CC3CCC4=C5C(=C(CC56C3(C(CC1C62O)O)C)C(=O)OC)CC4	385.50	unknown	https://doi.org/10.1021/NP060088F
methyl (1R,2S,3R,5S,6S,7R,8R,11S,17R,18R)-8-hydroxy-2,6-dimethyl-4-oxa-9-azaheptacyclo[12.5.1.13,7.01,8.02,11.05,9.017,20]henicos-14(20)-ene-18-carboxylate	162882788	Click to see CC1C2CC3C4(C5CCC6=C7C4(C2(N(C5)C1O3)O)CC(C7CC6)C(=O)OC)C	385.50	unknown	https://doi.org/10.1016/J.TETLET.2007.03.156
methyl (1R,3R,4R,10S,14S,15R,18R,19R)-18-(acetyloxymethyl)-19-hydroxy-14-methyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylate	21580233	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(CCC1C62O)COC(=O)C)C(=O)OC	429.50	unknown	https://doi.org/10.1021/NP040038F
methyl (1R,3R,4R,10S,14S,15R,18R,19S)-18-(acetyloxymethyl)-19-hydroxy-14-methyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylate	162943557	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(CCC1C62O)COC(=O)C)C(=O)OC	429.50	unknown	https://doi.org/10.1021/NP040038F
methyl (1R,3S,4S,10R,14S,15R,18R,19S)-15-hydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylate	162958315	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C2C1(CCC63C)O)C(=O)OC	371.50	unknown	https://doi.org/10.1002/HLCA.200900383
methyl (1S,10R,15R,18S,19R)-19-hydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icosa-3,7(20)-diene-3-carboxylate	102596796	Click to see CC1CN2CC3CCC4=C5C(=C(CC56C3(CCC1C62O)C)C(=O)OC)CC4	369.50	unknown	https://doi.org/10.1021/NP060088F
methyl (1S,2R,5S,6R,9S,10S,13R,19R)-2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.13,10.01,9.02,6.013,19.016,19]henicos-16-ene-17-carboxylate	25135428	Click to see CC1CN2CC3CCC45CCC6=C(CC7(C64O5)C3(CCC1C72O)C)C(=O)OC	385.50	unknown	https://doi.org/10.1021/NP800323M
methyl (1S,2R,6R,9S,10S,13S,19R)-2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.13,10.01,9.02,6.013,19.016,19]henicos-16-ene-17-carboxylate	102596797	Click to see CC1CN2CC3CCC45CCC6=C(CC7(C64O5)C3(CCC1C72O)C)C(=O)OC	385.50	unknown	https://doi.org/10.1021/NP060088F
methyl (1S,3R,4R,10S,14R,15S,18S,19R)-15-hydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylate	162958316	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C2C1(CCC63C)O)C(=O)OC	371.50	unknown	https://doi.org/10.1016/J.TET.2007.11.087
methyl (1S,3R,4R,10S,14S,15R,18S,19R)-19-hydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icosa-7(20),16-diene-3-carboxylate	163011797	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C=CC1C62O)C)C(=O)OC	369.50	unknown	https://doi.org/10.1016/J.TET.2007.11.087
methyl (1S,3S,4S,7S,10R,11R,14S,15R,18R,20R,21R)-11,15-dimethyl-19-oxa-17-azaheptacyclo[12.6.1.01,11.04,20.07,20.010,18.017,21]henicosane-3-carboxylate	162967923	Click to see CC1CN2C3C1CCC4(C35CC(C6C57C(CC6)CCC4C2O7)C(=O)OC)C	371.50	unknown	https://doi.org/10.1021/JO0203950
methyl (1S,8R,10R,15R,18S,19R)-8,19-dihydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icosa-3,7(20)-diene-3-carboxylate	102596795	Click to see CC1CN2CC3CC(C4=C5C(=C(CC56C3(CCC1C62O)C)C(=O)OC)CC4)O	385.50	unknown	https://doi.org/10.1021/NP060088F
Methyl 11,15-dimethyl-19-oxa-17-azaheptacyclo[12.6.1.01,11.04,20.07,20.010,18.017,21]henicosane-3-carboxylate	73112339	Click to see CC1CN2C3C1CCC4(C35CC(C6C57C(CC6)CCC4C2O7)C(=O)OC)C	371.50	unknown	https://doi.org/10.1021/JO0203950
Methyl 15-hydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylate	162958314	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C2C1(CCC63C)O)C(=O)OC	371.50	unknown	https://doi.org/10.1016/J.TET.2007.11.087 https://doi.org/10.1002/HLCA.200900383
Methyl 18-(acetyloxymethyl)-19-hydroxy-14-methyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icos-7(20)-ene-3-carboxylate	72787095	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(CCC1C62O)COC(=O)C)C(=O)OC	429.50	unknown	https://doi.org/10.1021/NP040038F
Methyl 19-hydroxy-14,18-dimethyl-12-azahexacyclo[10.6.1.11,4.010,18.015,19.07,20]icosa-7(20),16-diene-3-carboxylate	163011796	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C=CC1C62O)C)C(=O)OC	369.50	unknown	https://doi.org/10.1016/J.TET.2007.11.087
Methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.13,10.01,9.02,6.013,19.016,19]henicos-16-ene-17-carboxylate	74392112	Click to see CC1CN2CC3CCC45CCC6=C(CC7(C64O5)C3(CCC1C72O)C)C(=O)OC	385.50	unknown	https://doi.org/10.1021/NP800323M
Methyl 8-hydroxy-2,6-dimethyl-4-oxa-9-azaheptacyclo[12.5.1.13,7.01,8.02,11.05,9.017,20]henicos-14(20)-ene-18-carboxylate	162882787	Click to see CC1C2CC3C4(C5CCC6=C7C4(C2(N(C5)C1O3)O)CC(C7CC6)C(=O)OC)C	385.50	unknown	https://doi.org/10.1016/J.TETLET.2007.03.156
YuzurimineE	102074150	Click to see CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(CCC1C62O)COC(=O)C)C(=O)OC	429.50	unknown	via CMAUP database
> Organoheterocyclic compounds / Azepanes
(1S,2S,5R,6R,10S,16R,17R)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.05,8.016,19]icos-13(19)-ene-17-carboxylic acid	101839808	Click to see CC1CN2C13CCC4(C(C2)CCC5=C6C4(C3=O)CC(C6CC5)C(=O)O)C	355.50	unknown	https://doi.org/10.1016/J.TET.2007.11.087
2,6-Dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.05,8.016,19]icos-13(19)-ene-17-carboxylic acid	163022686	Click to see CC1CN2C13CCC4(C(C2)CCC5=C6C4(C3=O)CC(C6CC5)C(=O)O)C	355.50	unknown	https://doi.org/10.1016/J.TET.2007.11.087
methyl (1R,2R,5S,6S,10R,16S,17S)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.05,8.016,19]icos-13(19)-ene-17-carboxylate	163003197	Click to see CC1CN2C13CCC4(C(C2)CCC5=C6C4(C3=O)CC(C6CC5)C(=O)OC)C	369.50	unknown	https://doi.org/10.1016/J.TETLET.2006.12.139
Methyl 2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.05,8.016,19]icos-13(19)-ene-17-carboxylate	163003195	Click to see CC1CN2C13CCC4(C(C2)CCC5=C6C4(C3=O)CC(C6CC5)C(=O)OC)C	369.50	unknown	https://doi.org/10.1016/J.TETLET.2006.12.139
> Organoheterocyclic compounds / Cycloheptapyrans
methyl (2S,3S,5R,6S,10S)-3-hydroxy-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.15,19.02,10.03,8.017,20]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate	162999165	Click to see CC1CN2CC3CCC4=C5C(=C(C6=C5C3(C2(CC1C6=O)O)C)C(=O)OC)C=CO4	395.40	unknown	https://doi.org/10.1002/HLCA.200900027
Methyl 3-hydroxy-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.15,19.02,10.03,8.017,20]henicosa-1(19),13(20),15,17-tetraene-18-carboxylate	162999164	Click to see CC1CN2CC3CCC4=C5C(=C(C6=C5C3(C2(CC1C6=O)O)C)C(=O)OC)C=CO4	395.40	unknown	https://doi.org/10.1002/HLCA.200900027
> Organoheterocyclic compounds / Indoles and derivatives
calyciphylline N	25209367	Click to see CC1CN=C2C13CCC4(C25CC(C6C5=C(CC6)CCC4C3O)C(=O)OC)C	369.50	unknown	https://doi.org/10.1021/NP800515S
methyl (1S,5S,6R,9S,10S,16R,17R)-20-hydroxy-5,9-dimethyl-3-azahexacyclo[11.5.1.16,10.01,9.02,6.016,19]icosa-2,13(19)-diene-17-carboxylate	102282914	Click to see CC1CN=C2C13CCC4(C25CC(C6C5=C(CC6)CCC4C3O)C(=O)OC)C	369.50	unknown	https://doi.org/10.1021/NP800515S
> Organoheterocyclic compounds / Indolizidines
(3-Ethyl-16-methyl-1-azapentacyclo[9.6.1.02,15.03,12.04,8]octadec-4-en-12-yl)methanol	162878740	Click to see CCC12C3C4CCC1(C(CCC5C2=CCC5)CN3CC4C)CO	315.50	unknown	https://doi.org/10.3184/030823408X314491
[(2R,3R,8S,11S,12R,15R,16S)-3-ethyl-16-methyl-1-azapentacyclo[9.6.1.02,15.03,12.04,8]octadec-4-en-12-yl]methanol	162878741	Click to see CCC12C3C4CCC1(C(CCC5C2=CCC5)CN3CC4C)CO	315.50	unknown	https://doi.org/10.3184/030823408X314491
3-(12,16-Dimethyl-1-azapentacyclo[9.6.1.02,15.03,12.04,8]octadec-4-en-3-yl)propanoic acid	162941153	Click to see CC1CN2CC3CCC4CCC=C4C5(C2C1CCC35C)CCC(=O)O	343.50	unknown	https://doi.org/10.1016/J.TET.2005.03.146
3-[(2S,3S,8S,11S,12S,15R,16S)-12,16-dimethyl-1-azapentacyclo[9.6.1.02,15.03,12.04,8]octadec-4-en-3-yl]propanoic acid	162941154	Click to see CC1CN2CC3CCC4CCC=C4C5(C2C1CCC35C)CCC(=O)O	343.50	unknown	https://doi.org/10.1016/J.TET.2005.03.146
Caldaphnidine N	102596801	Click to see CC1CN2CC3(CCC4CCCC4C56C2C1CCC35COC(=O)CC6)O	359.50	unknown	https://doi.org/10.1021/NP060088F
methyl (1S,2S,3S,5S,10R)-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.11,5.02,10.03,8.017,20]henicosa-13(20),17-diene-18-carboxylate	137705480	Click to see CC1CN2CC3CCC4=C5C(=C(CC56C3(C2CC1C6=O)C)C(=O)OC)CCO4	383.50	unknown	https://doi.org/10.1021/NP060088F
methyl 3-[(2S,3R,4R,8S,11S,12R,15R)-11-hydroxy-12,16-dimethyl-1-azapentacyclo[9.6.1.02,15.03,12.04,8]octadecan-3-yl]propanoate	102596803	Click to see CC1CN2CC3(CCC4CCCC4C5(C2C1CCC35C)CCC(=O)OC)O	375.50	unknown	https://doi.org/10.1021/NP060088F
> Organoheterocyclic compounds / Lactones / Gamma butyrolactones
4-Methylene-5beta-hydroperoxyovatodiolide	24970924	Click to see CC1=CC2C(CCC(=C)C(CCC3=CC(C1)OC3=O)OO)C(=C)C(=O)O2	360.40	unknown	via CMAUP database
4alpha-Hydroperoxy-5-enovatodiolide	24970923	Click to see CC1=CC2C(CCC(C=CCC3=CC(C1)OC3=O)(C)OO)C(=C)C(=O)O2	360.40	unknown	via CMAUP database
> Organoheterocyclic compounds / Quinolidines
Calyciphylline B	11132065	Click to see CC1C[N+]2(C3C(CCC4C3=CCC4)C5(C6(C2C1CC6)CCC(=O)O5)C)[O-]	357.50	unknown	https://doi.org/10.1021/NP060088F
CID 5243215	5243215	Click to see CC1CN2C3C(CCC4C3=CCC4)C5(C6(C2C1CC6)CCC(=O)O5)C	341.50	unknown	https://doi.org/10.1002/HLCA.200900027
Deoxycalyciphylline B	10871573	Click to see CC1CN2C3C(CCC4C3=CCC4)C5(C6(C2C1CC6)CCC(=O)O5)C	341.50	unknown	https://doi.org/10.1002/HLCA.200900027
Deoxyisocalyciphylline B	10871574	Click to see CC1CN2C3C(CCC4C3=CCC4)C5(C6(C2C1CC6)CCC(=O)O5)C	341.50	unknown	https://doi.org/10.1002/HLCA.200900027
Methyl 3-(11-hydroxy-11,16-dimethyl-1-azapentacyclo[10.5.1.02,10.03,7.015,18]octadec-3-en-12-yl)propanoate	74392197	Click to see CC1CN2C3C(CCC4C3=CCC4)C(C5(C2C1CC5)CCC(=O)OC)(C)O	373.50	unknown	https://doi.org/10.1021/NP800323M
Methyl 3-(11-hydroxy-13,17-dimethyl-1-azahexacyclo[9.7.1.02,16.03,13.04,8.08,19]nonadecan-3-yl)propanoate	163050051	Click to see CC1CN2C3C1CCC4(C3(C5CCCC56C2C(C4)(CC6)O)CCC(=O)OC)C	387.60	unknown	https://doi.org/10.1021/NP800323M
Methyl 3-(13,17-dimethyl-1-azahexacyclo[9.7.1.02,16.03,13.04,8.08,19]nonadecan-3-yl)propanoate	162902615	Click to see CC1CN2C3C4CCC35CCCC5C6(C2C1CCC6(C4)C)CCC(=O)OC	371.60	unknown	https://doi.org/10.1021/NP800323M
methyl 3-[(2R,3S,4S,8S,11R,13R,16S,17R,19S)-13,17-dimethyl-1-azahexacyclo[9.7.1.02,16.03,13.04,8.08,19]nonadecan-3-yl]propanoate	162902616	Click to see CC1CN2C3C4CCC35CCCC5C6(C2C1CCC6(C4)C)CCC(=O)OC	371.60	unknown	https://doi.org/10.1021/NP800323M
methyl 3-[(2R,3S,4S,8S,11S,13R,16S,17R,19R)-11-hydroxy-13,17-dimethyl-1-azahexacyclo[9.7.1.02,16.03,13.04,8.08,19]nonadecan-3-yl]propanoate	163050052	Click to see CC1CN2C3C1CCC4(C3(C5CCCC56C2C(C4)(CC6)O)CCC(=O)OC)C	387.60	unknown	https://doi.org/10.1021/NP800323M
methyl 3-[(2R,7R,10S,11S,12S,15R,16S,18S)-11-hydroxy-11,16-dimethyl-1-azapentacyclo[10.5.1.02,10.03,7.015,18]octadec-3-en-12-yl]propanoate	25135570	Click to see CC1CN2C3C(CCC4C3=CCC4)C(C5(C2C1CC5)CCC(=O)OC)(C)O	373.50	unknown	https://doi.org/10.1021/NP060088F
methyl 3-[(2S,7S,10R,11R,12R,15S,16R,18R)-11-hydroxy-11,16-dimethyl-1-azapentacyclo[10.5.1.02,10.03,7.015,18]octadec-3-en-12-yl]propanoate	162940019	Click to see CC1CN2C3C(CCC4C3=CCC4)C(C5(C2C1CC5)CCC(=O)OC)(C)O	373.50	unknown	https://doi.org/10.1021/NP800323M
> Organoheterocyclic compounds / Tetrahydroisoquinolines
Fumaricine	609998	Click to see CN1CCC2=CC(=C(C=C2C13CC4=C(C3O)C5=C(C=C4)OCO5)OC)OC	369.40	unknown	via CMAUP database
> Phenylpropanoids and polyketides / 2-arylbenzofuran flavonoids
Cedrusin	11210164	Click to see COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)CCCO)O)CO)O	346.40	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Cinnamic acids and derivatives / Hydroxycinnamic acids and derivatives / Coumaric acids and derivatives
Martynoside	5319292	Click to see CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)OC)CO)OCCC4=CC(=C(C=C4)OC)O)O)O)O)O	652.60	unknown	via CMAUP database
Verbascoside	5281800	Click to see CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O	624.60	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid O-glycosides / Flavonoid-3-O-glycosides
5,6,7-trihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one	163031673	Click to see CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=C(C3=O)C(=C(C(=C4)O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O	610.50	unknown	https://doi.org/10.1021/NP9800203
5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one	74978457	Click to see CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=C(C3=O)C(=C(C(=C4)O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O	610.50	unknown	https://doi.org/10.1021/NP9800203
5,6,7,4'-Tetrahydroxyflavonol 3-O-rutinoside	10371537	Click to see CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=C(C3=O)C(=C(C(=C4)O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O	610.50	unknown	https://doi.org/10.1021/NP9800203
> Phenylpropanoids and polyketides / Flavonoids / O-methylated flavonoids / 4-O-methylated flavonoids
Acacetin	5280442	Click to see COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O	284.26	unknown	via CMAUP database

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Daphniphyllum calycinum

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