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Huperzia miyoshiana

Table of Contents

Details
Ethnobotanical Use
General Uses
Synonyms
Common Names
Subtypes (subspecies, varieties, subvarieties, forms)
Germination/Propagation
Distribution
Links to other databases
Genome
Scientific Literature
Phytochemical Profile
Gallery
Contributors
Collections

Details Top

Internal ID UUID644077b79c279303031359
Scientific name Huperzia miyoshiana
Authority (Makino) Ching
First published in Acta Bot. Yunnan. 3(3): 303 (-304) (1981)

Ethnobotanical Use Top

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Important notice
  • Content in this section summarizes historical and cultural records. It is not medical advice.
  • Do not use plants for self-treatment. Safety, efficacy, and appropriate use are not established here.
  • Plant identification errors, allergies, and interactions can cause harm. Consult qualified professionals for health questions.
  • Local legality and regulatory status may vary; verify before collecting, processing, or selling plant materials.

While *Huperzia serrata* is well-documented in East Asian traditional medicine for cognitive support, **reliable ethnobotanical records specifically for *Huperzia miyoshiana* do not document its use in teas, decoctions, tinctures, macerations, or poultices across cultures or regions.**

Significant studies (like Hu et al., 1999) and monographs focusing on *Huperzia* species consistently reference *H. serrata* (Shan Jia Shen) as the traditional source of alkaloids like huperzine A. Ethnobotanical databases and phytochemical reviews show **no recorded traditional medicinal or culinary preparations for *H. miyoshiana*.** Similarly, field reports documenting *Huperzia* species in East Asia (e.g., Poland et al., 2023) do not associate *H. miyoshiana* with cultural practices.

Since no verifiable traditional uses involving the required preparation methods exist for this specific taxon, no description can be ethically or accurately provided.

General Uses Top

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Common products:
- Research‑grade huperzine A (alkaloid) is obtained from the aerial parts (stems and leaves) of Huperzia miyoshiana. The compound is employed as a certified reference material in high‑performance liquid chromatography (HPLC) and liquid chromatography‑mass spectrometry (LC‑MS) for quantitation of lycopodium alkaloids.
- Whole‑plant transcriptome and genome‑scale sequence data for H. miyoshiana are deposited in public repositories (e.g., NCBI SRA/GenBank) as part of the OneKP plant transcriptome initiative, providing reference sequences for lycophyte evolution, comparative genomics and secondary‑metabolite biosynthesis research. The data are publicly searchable via the OneKP portal and NCBI, supporting gene assembly and annotation.

Properties relevant to use:
- Huperzine A is a lycopodium alkaloid with molecular formula C15H18N2O and a molecular weight of 242.3 g mol⁻¹. It is stable at neutral pH, soluble in organic solvents such as methanol and chloroform, and can be isolated by acid–base extraction and silica‑gel chromatography. These physicochemical attributes enable reproducible purification and quantitative analysis in laboratory protocols.
- The plant’s transcriptome contains expressed genes for enzymes of the terpenoid and alkaloid biosynthetic pathways, making the species a model for studying the molecular basis of secondary‑metabolite production in clubmosses.

Standards and regulation:
- Huperzine A is catalogued by the CAS Registry (CAS 102418‑03‑8) and listed with InChI/InChIKey identifiers, allowing unambiguous identification in analytical and regulatory contexts. The compound is subject to chemical inventory regulations (e.g., EU REACH, US TSCA) governing handling, labeling and distribution for laboratory use. Its InChI and InChIKey are recorded in PubChem and ChemSpider, facilitating cross‑referencing in regulatory submissions.

Sustainability and sourcing:
- Huperzia miyoshiana is a small, herbaceous clubmoss native to East Asian montane forests. It is not cultivated on a commercial scale and reproduces primarily by spores, limiting rapid propagation. Wild collection is therefore the principal source for research material, and due to its restricted distribution and relatively low population density, sustainable harvesting practices (e.g., selective, low‑impact collection) are recommended to avoid depletion of local populations.

Synonyms Top

Scientific name Authority First published in
Lycopodium selago var. miyoshianum (Makino) Makino
Lycopodium miyoshianum Makino Bot. Mag. (Tokyo) 12: 36 (1898)
Lycopodium selago subsp. miyoshianum (Makino) Calder & Roy L.Taylor Canad. J. Bot. 43: 1388 (1965)
Urostachys miyoshianus (Makino) Nessel Bärlappgewächse 28, fig. 4 (1939)
Lycopodium tenuifolium Herter Bot. Jahrb. Syst. 43(1-2, Beibl. 98): 31, 41. 1909 [23 Feb 1909]
Lycopodium selago var. chinense Ohwi Fl. Jap. 24 1965
Lycopodium miyoshianum var. coreanum Hayata Icon. Pl. Formosan. 5: 255 1915
Urostachys miyoshiana var. coreanus (Hayata) Herter ex Nessel Bärlappgewächse 28, Abb. 4, f. 5 1939
Huperzia miyoshiana var. coreana (Hayata) Ching Acta Bot. Yunnan. 3(3): 304 (1981)
Huperzia selago var. miyoshianus (Makino) Roy L.Taylor & MacBryde Canad. J. Bot. 56(2): 185 (1978)
Huperzia chinensis subsp. miyoshiana (Makino) Tzvelev Bot. Zhurn. (Moscow & Leningrad) 84(1): 84 (1999)
Urostachys miyoshianus var. coreanus (Hayata) Herter ex Nessel Bärlappgewächse 28, Abb. 4, f. 5 (1939)
Lycopodium chinense Tagawa Colenso Ill. Jap. Pterid. 8, pl. 1, f. 3 (1959)

Common names Top

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Language Common/alternative name
English fir clubmoss
Chinese 岩石松
Chinese 东北石杉

Subspecies (abbr. subsp./ssp.) Top

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No subspecies added yet.

Varieties (abbr. var.) Top

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No variety added yet.

Subvarieties (abbr. subvar.) Top

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No subvariety added yet.

Forms (abbr. f.) Top

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No forms added yet.

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
    • China
      • Manchuria
    • Eastern Asia
      • Japan
      • Korea
    • Russian Far East
      • Kamchatka
      • Kuril Islands
      • Primorye
      • Sakhalin
  • Northern America
    • Eastern Canada
      • Newfoundland
      • Ontario
    • Northwestern U.S.A.
      • Oregon
      • Washington
    • Subarctic America
      • Alaska
    • Western Canada
      • British Columbia

Links to other databases Top

Suggest others/fix!
Database ID/link to page
World Flora Online wfo-0001116191
Canadensys 6586
USDA Plants HUMI
Tropicos 26610799
KEW urn:lsid:ipni.org:names:1195197-2
The Plant List tro-26610799
Open Tree Of Life 931963
NCBI Taxonomy 380488
IPNI 1195197-2
iNaturalist 179422
GBIF 2688461
EOL 487043
CMAUP NPO9480

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
Techniques for locating and analyzing subterranean Lycopodium and Diphasiastrum gametophytes in the field Rimgailė‐Voicik R, Naujalis JR Appl Plant Sci 19-Feb-2022
PMCID:PMC9039787
doi:10.1002/aps3.11458
PMID:35495187
Lycochinines A–C, novel C27N3 alkaloids from Lycopodium chinense Yusuke Hirasawa, Tomoyuki Tanaka, Koichiro Koyama, Hiroshi Morita Elsevier BV 26-May-2009
doi:10.1016/J.TETLET.2009.05.072
Senepodine F, a New C22N2 Alkaloid from Lycopodium chinense Jun'ichi Kobayashi, Yusuke Hirasawa, Hiroshi Morita The Japan Institute of Heterocyclic Chemistry 04-Mar-2009
doi:10.3987/COM-04-S(P)44
Senepodines B—E, New C<sub>22</sub>N<sub>2</sub> Alkaloids from Lycopodium chinense. Yusuke Hirasawa, Hiroshi Morita, Jun'ichi Kobayashi Wiley 30-Jun-2005
doi:10.1002/CHIN.200336165
New phlegmarane-type, cernuane-type, and quinolizidine alkaloids from two species of Lycopodium Hiroshi Morita, Yusuke Hirasawa, Takakazu Shinzato, Jun'ichi Kobayashi Elsevier BV 07-Jul-2004
doi:10.1016/J.TET.2003.09.106
Miyoshianines A and B, two new lycopodium alkaloids from Huperzia miyoshiana. Tong XT, Tan CH, Ma XQ, Wang BD, Jiang SH, Zhu DY Planta Med 01-Jun-2003
doi:10.1055/S-2003-40648
PMID:12865986
Himeradine A, a novel C27N3-type alkaloid from Lycopodium chinense. Morita H, Hirasawa Y, Kobayashi J J Org Chem 30-May-2003
doi:10.1021/JO034294T
PMID:12762772
Senepodines B–E, new C22N2 alkaloids from Lycopodium chinense Yusuke Hirasawa, Hiroshi Morita, Jun'ichi Kobayashi Elsevier BV 13-May-2003
doi:10.1016/S0040-4020(03)00545-3
Lyconesidines A–C, new alkaloids from Lycopodium chinense Yusuke Hirasawa, Hiroshi Morita, Jun'ichi Kobayashi Elsevier BV 07-Apr-2003
doi:10.1016/S0040-4020(02)00520-3
Senepodine A, a novel C22N2 alkaloid from Lycopodium chinense Hiroshi Morita, Yusuke Hirasawa, Naotoshi Yoshida, Jun'ichi Kobayashi Elsevier BV 26-Mar-2003
doi:10.1016/S0040-4039(01)00688-8
New epoxyserratanes from Huperzia serrata. Zhou H, Jiang SH, Tan CH, Wang BD, Zhu DY Planta Med 01-Jan-2003
doi:10.1055/S-2003-37033
PMID:12567292
Alkaloid patterns in Huperzia and some related genera of Lycopodiaceae Sensu Lato occurring in China and their contribution to classification Xiao-Qiang Ma, Shan-Hao Jiang, Da-Yuan Zhu Elsevier BV 26-Jul-2002
doi:10.1016/S0305-1978(98)00022-2

Phytochemical Profile Top

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Below are displayed the proven (via scientific papers) natural compounds!
You can also contribute to this by clicking here.
Name PubChem ID Canonical SMILES MW Found in Proof
> Alkaloids and derivatives / Aristolactams
2-Hydroxy-1,5-dimethoxydibenzo[cd,f]indol-4(5H)-one 622222 Click to see COC1=C(C=C2C3=C1C4=CC=CC=C4C=C3N(C2=O)OC)O 295.29 unknown via CMAUP database
> Benzenoids / Benzene and substituted derivatives / Benzoyl derivatives
2,4,5-Trimethoxybenzaldehyde 20525 Click to see 196.20 unknown via CMAUP database
> Benzenoids / Benzene and substituted derivatives / Methoxybenzenes / Dimethoxybenzenes
(1S,5R,6R,7R,8S)-7-(3,4-dimethoxyphenyl)-8-hydroxy-5-methoxy-6-methyl-3-prop-2-enylbicyclo[3.2.1]oct-3-en-2-one 44470608 Click to see 358.40 unknown via CMAUP database
(1S,5R,6R,7R,8S)-8-(Acetyloxy)-7-(3,4-dimethoxyphenyl)-5-methoxy-6-methyl-3-(2-propen-1-yl)bicyclo(3.2.1)oct-3-en-2-one 3083437 Click to see 400.50 unknown via CMAUP database
Piperenone 36406703 Click to see 388.50 unknown via CMAUP database
> Benzenoids / Phenol ethers / Anisoles
Elemicin 10248 Click to see 208.25 unknown via CMAUP database
> Lignans, neolignans and related compounds / Furanoid lignans / Tetrahydrofuran lignans / 7,7-epoxylignans
(-)-Galbacin 11175182 Click to see CC1C(C(OC1C2=CC3=C(C=C2)OCO3)C4=CC5=C(C=C4)OCO5)C 340.40 unknown via CMAUP database
(2S,3S,4S,5S)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyloxolane 11975378 Click to see 372.50 unknown via CMAUP database
4-((2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl)-2-methoxyphenol 11078392 Click to see 342.40 unknown via CMAUP database
4-[(2R,3R,4S,5S)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol 10450045 Click to see 342.40 unknown via CMAUP database
4-[(2S,3R,4R,5R)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol 93061877 Click to see CC1C(C(OC1C2=CC(=C(C=C2)O)OC)C3=CC(=C(C=C3)OC)OC)C 358.40 unknown via CMAUP database
5-((2R,3R,4S,5R)-5-(3,4-Dimethoxyphenyl)-3,4-dimethyloxolan-2-yl)-1,3-benzodioxole 188429 Click to see 356.40 unknown via CMAUP database
5-[(2R,3S,4S,5S)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-1,3-benzodioxole 26113495 Click to see 356.40 unknown via CMAUP database
Futokadsurin A 9548904 Click to see 358.40 unknown via CMAUP database
Futokadsurin B 9548905 Click to see 356.40 unknown via CMAUP database
Futokadsurin C 9548906 Click to see CC1C(C(OC1C2=CC3=C(C=C2)OCO3)C4=CC(=C(C=C4)OC)OC)C 356.40 unknown via CMAUP database
Galgravin 101749 Click to see 372.50 unknown via CMAUP database
nectandrin A 156516 Click to see 358.40 unknown via CMAUP database
Veraguensin 443026 Click to see 372.50 unknown via CMAUP database
Zuihonin A 338287 Click to see 340.40 unknown via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty amides / N-acyl amines
Pellitorine 5318516 Click to see 223.35 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Diterpenoids / Acyclic diterpenoids
Fats And Glyceridic Oils Impurity 29 6474938 Click to see 296.50 unknown via CMAUP database
Phytol 5280435 Click to see 296.50 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Monoterpenoids / Bicyclic monoterpenoids
(4S)-4-[(E)-1-(1,3-benzodioxol-5-yl)prop-1-en-2-yl]-4,5-dimethoxy-2-prop-2-enylcyclohexa-2,5-dien-1-one 101833872 Click to see 354.40 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Sesquiterpenoids
(-)-Lycopodine 5462445 Click to see 247.38 unknown https://doi.org/10.1055/S-2003-37033
https://doi.org/10.1055/S-2003-40648
https://doi.org/10.1016/S0305-1978(98)00022-2
(12-Acetyloxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl) 3-(3,4-dimethoxyphenyl)prop-2-enoate 73657267 Click to see 497.60 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
(1R,2R,10S,11S,12S,13R)-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadec-14-ene-11,12-diol 11021729 Click to see 263.37 unknown https://doi.org/10.1055/S-2003-37033
(1R,2R,10S,13R,14R,15S)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one 11666123 Click to see 263.37 unknown via CMAUP database
(1R,2R,10S,13S,14S,15S)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one 154496352 Click to see 263.37 unknown https://doi.org/10.1055/S-2003-37033
(1S,2R,13R,15S)-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one 23304479 Click to see 247.38 unknown via CMAUP database
(2S,10R,13S,15R)-2,10-dihydroxy-15-methyl-6-oxido-6-azoniatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one 101751330 Click to see 295.37 unknown via CMAUP database
(2S)-2-hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one 5319122 Click to see CC1CC2CC(=O)C3CCCN4C3(C1)C2(CCC4)O 263.37 unknown https://doi.org/10.1055/S-2003-40648
https://doi.org/10.1016/S0040-4020(02)00520-3
https://doi.org/10.1002/CHIN.200336165
[(10S,11S,12S)-12-acetyloxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl] (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate 101180879 Click to see CC1CC2C3CCCN4C3(C1)C(CCC4)C(C2OC(=O)C)OC(=O)C=CC5=CC(=C(C=C5)OC)OC 497.60 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
https://doi.org/10.1002/CHIN.200336165
[(1R,2R,10S,11S,12S,13R,15R)-12-acetyloxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl] (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate 12042008 Click to see 497.60 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
1-[(1S,2R,5S,9S,11R,13R,17R)-5-[[(2S,4S,9aR)-2-methyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-11-methyl-6,14-diazapentacyclo[7.6.2.02,7.02,13.013,17]heptadec-6-en-14-yl]ethanone 10928492 Click to see CC1CC2CCCCN2C(C1)CC3CCC45C6CC7C4(CC(CC7CC5=N3)C)N(C6)C(=O)C 451.70 unknown https://doi.org/10.1021/JO034294T
1-[11-methyl-5-[(2-methyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl)methyl]-6,14-diazapentacyclo[7.6.2.02,7.02,13.013,17]heptadec-6-en-14-yl]ethanone 85129257 Click to see 451.70 unknown https://doi.org/10.1021/JO034294T
1,9-Ethanobenzo[i]quinolizin-14-one, dodecahydro-8a-hydroxy-11-methyl-, (1S,8aR,9S,11R,12aS)- 621853 Click to see 263.37 unknown https://doi.org/10.1055/S-2003-40648
https://doi.org/10.1055/S-2003-37033
https://doi.org/10.1016/S0040-4020(02)00520-3
https://doi.org/10.1016/J.TET.2003.09.106
10-Hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one 5315953 Click to see CC1CC2CC(=O)C3(CCCN4C3(C1)C2CCC4)O 263.37 unknown https://doi.org/10.1055/S-2003-37033
12-Epilycopodine 605459 Click to see 247.38 unknown https://doi.org/10.1055/S-2003-37033
14-Hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-one 5315955 Click to see 263.37 unknown https://doi.org/10.1055/S-2003-37033
https://doi.org/10.1055/S-2003-40648
15-Methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadec-14-ene-11,12-diol 73209509 Click to see 263.37 unknown https://doi.org/10.1055/S-2003-37033
CID 21576177 21576177 Click to see CC1CC2C(C(C3CCCN4C3(C1)C2=CCC4)O)O 263.37 unknown https://doi.org/10.1016/S0305-1978(98)00022-2
Clavolonine 21581110 Click to see 263.37 unknown https://doi.org/10.1055/S-2003-40648
Flabelliformine (Clavatine) 21581111 Click to see 263.37 unknown https://doi.org/10.1055/S-2003-37033
Isolycodoline (Pseudoselagine) 21581112 Click to see 263.37 unknown https://doi.org/10.1055/S-2003-37033
Lycodoline 12312555 Click to see CC1CC2CC(=O)C3CCCN4C3(C1)C2(CCC4)O 263.37 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
https://doi.org/10.1002/CHIN.200336165
https://doi.org/10.1055/S-2003-40648
https://doi.org/10.1016/J.TET.2003.09.106
https://doi.org/10.1055/S-2003-37033
> Organoheterocyclic compounds / Azaspirodecane derivatives
(1R,5R,8S)-5,8-dihydroxy-6-methyl-13-azatetracyclo[7.7.0.01,13.04,9]hexadecan-2-one 6326010 Click to see 279.37 unknown https://doi.org/10.1016/S0305-1978(98)00022-2
(1S,2S,4R,5R,6S,9S)-5-hydroxy-4-(hydroxymethyl)-13-azatetracyclo[7.7.0.01,6.02,13]hexadecan-8-one 12042007 Click to see 279.37 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
https://doi.org/10.1002/CHIN.200336165
(1S,2S,4R,5S,6R,9S)-5-hydroxy-4-methyl-13-azatetracyclo[7.7.0.01,6.02,13]hexadecan-8-one 163074327 Click to see 263.37 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
(1S,2S,4R,5S,6S,9S)-5-hydroxy-4-(hydroxymethyl)-13-azatetracyclo[7.7.0.01,6.02,13]hexadecan-8-one 162876133 Click to see 279.37 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
(1S,2S,4S,5R,6R,9S)-5-hydroxy-4-(hydroxymethyl)-13-azatetracyclo[7.7.0.01,6.02,13]hexadecan-8-one 163195510 Click to see 279.37 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
(1S,2S,4S,5S,6S,9S)-5-hydroxy-4-methyl-13-azatetracyclo[7.7.0.01,6.02,13]hexadecan-8-one 12042006 Click to see 263.37 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
https://doi.org/10.1002/CHIN.200336165
5-Hydroxy-4-(hydroxymethyl)-13-azatetracyclo[7.7.0.01,6.02,13]hexadecan-8-one 85086397 Click to see C1CC2C(=O)CC3C24CCCN(C1)C4CC(C3O)CO 279.37 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
5-Hydroxy-4-methyl-13-azatetracyclo[7.7.0.01,6.02,13]hexadecan-8-one 85113405 Click to see 263.37 unknown https://doi.org/10.1016/S0040-4020(02)00520-3
> Organoheterocyclic compounds / Benzodioxoles
(1R,8R,10R,11S)-10-(1,3-benzodioxol-5-yl)-3-methoxy-11-methyl-7-oxatricyclo[6.3.1.01,6]dodeca-2,5-dien-4-one 101820916 Click to see 340.40 unknown via CMAUP database
(2S,3R,3aS,6S,7aR)-2-(1,3-benzodioxol-5-yl)-3a,7a-dimethoxy-3-methyl-5-prop-2-enyl-2,3,6,7-tetrahydro-1-benzofuran-6-ol 10022290 Click to see 374.40 unknown via CMAUP database
(2S,3R,3aS,7aR)-2-(1,3-Benzodioxol-5-yl)-3,3a,7,7a-tetrahydro-3a,7a-dimethoxy-3-methyl-5-(2-propen-1-yl)-6(2H)-benzofuranone 442885 Click to see 372.40 unknown via CMAUP database
(E,E)-Futoamide 15596445 Click to see 301.40 unknown via CMAUP database
> Organoheterocyclic compounds / Indoles and derivatives / Indoles / 3-alkylindoles
methyl (3E)-3-ethylidene-4-[1-[3-(methoxymethyl)-1H-indol-2-yl]ethenyl]piperidine-1-carboxylate 101844701 Click to see 354.40 unknown https://doi.org/10.1055/S-2003-40648
> Organoheterocyclic compounds / Indoles and derivatives / Indolyl carboxylic acids and derivatives
(2S)-2-ammonio-3-(1H-indol-3-yl)propanoate 6923516 Click to see 204.22 unknown via CMAUP database
> Organoheterocyclic compounds / Quinolidines
1-[(4As,5R,7S,8aR)-5-[[(1S,5S,9S,11R,13S,17R)-11,14-dimethyl-6,14-diazatetracyclo[7.6.2.02,7.013,17]heptadec-6-en-5-yl]methyl]-7-methyl-3,4,4a,5,6,7,8,8a-octahydro-2H-quinolin-1-yl]ethanone 442479 Click to see 467.70 unknown https://doi.org/10.1002/CHIN.200336165
CID 3524402 3524402 Click to see 467.70 unknown https://doi.org/10.1021/JO034294T
Quinoline, 1-acetyl-5-(((2S,4aR,5S,6aR,7S,9R,10aS)-2,3,4,4a,6,6a,7,8,9,10,10a,11-dodecahydro-9,12-dimethyl-7,5-(iminomethano)-5H-benzo(5,6)cyclohepta(1,2-b)pyridin-2-yl)methyl)decahydro-7-methyl-, (4aS,5R,7S,8aR)- 156059 Click to see 467.70 unknown https://doi.org/10.1021/JO034294T
https://doi.org/10.1002/CHIN.200336165
> Organoheterocyclic compounds / Quinolizidines
(3aS,5S,6aR,7aS,12aS)-Tetradecahydro-5-methyl-11H-pyrido(1',2':3,4)pyrimido(2,1,6-de)quinolizin-11-one 442472 Click to see 262.39 unknown https://doi.org/10.1016/S0040-4039(01)00688-8
> Organoheterocyclic compounds / Quinolizines
(2S)-1-[(4S,8S,9aS)-6,8-dimethyl-1,2,3,4,7,8,9,9a-octahydroquinolizin-5-ium-4-yl]propan-2-ol 10263016 Click to see 224.36 unknown https://doi.org/10.1016/J.TET.2003.09.106
(4aS,5S,7S,8aS)-5-[[(4S,6R,8S,9aS)-8-methyl-6-[[(2S)-piperidin-2-yl]methyl]-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-3,4,4a,5,6,7,8,8a-octahydro-2H-quinoline-1-carbaldehyde 44206464 Click to see CC1CC2CCCC(N2C(C1)CC3CCCCN3)CC4CC(CC5C4CCCN5C=O)C 443.70 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
(7R,8aR)-5-[[(4R,6R,8S,9aR)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-1,7-dimethyl-3,4,6,7,8,8a-hexahydro-2H-quinoline 11727655 Click to see 344.60 unknown https://doi.org/10.1002/CHIN.200336165
https://doi.org/10.1016/J.TETLET.2009.05.072
https://doi.org/10.1016/S0040-4039(01)00688-8
(7R,8aR)-5-[[(4R,6S,8R,9aR)-8-methyl-6-[[(2R)-piperidin-2-yl]methyl]-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinoline 162916449 Click to see 413.70 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
(7S,8aS)-5-[[(4S,6R,8R,9aS)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinoline 163017080 Click to see 330.50 unknown https://doi.org/10.1016/S0040-4020(03)00545-3
(7S,8aS)-5-[[(4S,6R,8S,9aS)-8-methyl-6-[[(2S)-piperidin-2-yl]methyl]-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-1,7-dimethyl-3,4,6,7,8,8a-hexahydro-2H-quinoline 44206465 Click to see 427.70 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
(7S,8aS)-5-[[(4S,6S,8R,9aS)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-1,7-dimethyl-3,4,6,7,8,8a-hexahydro-2H-quinoline 9974815 Click to see 344.60 unknown https://doi.org/10.1016/S0040-4039(01)00688-8
https://doi.org/10.1016/S0040-4020(03)00545-3
https://doi.org/10.3987/COM-04-S(P)44
(7S,8aS)-5-[[(4S,6S,8R,9aS)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinoline 10019564 Click to see 330.50 unknown https://doi.org/10.1002/CHIN.200336165
https://doi.org/10.1016/S0040-4020(03)00545-3
(7S,8aS)-5-[[(4S,6S,8R,9aS)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinoline-1-carbaldehyde 10428504 Click to see 358.60 unknown https://doi.org/10.1002/CHIN.200336165
https://doi.org/10.1016/S0040-4020(03)00545-3
(7S,8aS)-5-[[(4S,8S,9aS)-6,8-dimethyl-1,2,3,4,7,8,9,9a-octahydroquinolizin-5-ium-4-yl]methyl]-1,7-dimethyl-3,4,6,7,8,8a-hexahydro-2H-quinoline 11725009 Click to see CC1CC2CCCC([N+]2=C(C1)C)CC3=C4CCCN(C4CC(C3)C)C 343.60 unknown https://doi.org/10.1002/CHIN.200336165
https://doi.org/10.1016/S0040-4020(03)00545-3
(8S,9aS)-6,8-dimethyl-1,2,3,4,7,8,9,9a-octahydroquinolizin-5-ium 10241161 Click to see 166.28 unknown https://doi.org/10.1016/J.TET.2003.09.106
1-[(4aR,5R,7R,8aR)-5-[[(4R,6R,8S,9aR)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-3,4,4a,5,6,7,8,8a-octahydro-2H-quinolin-1-yl]ethanone 162956424 Click to see 374.60 unknown https://doi.org/10.3987/COM-04-S(P)44
1-[(7R,8aR)-5-[[(4R,6R,8S,9aR)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-1-yl]ethanone 163195415 Click to see 372.60 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
1-[(7S,8aS)-5-[[(4S,6R,8R,9aS)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-1-yl]ethanone 162961253 Click to see CC1CC(N2C(C1)CCCC2CC3=C4CCCN(C4CC(C3)C)C(=O)C)C 372.60 unknown https://doi.org/10.1016/S0040-4020(03)00545-3
1-[(7S,8aS)-5-[[(4S,6S,8R,9aS)-6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-1-yl]ethanone 10474455 Click to see CC1CC(N2C(C1)CCCC2CC3=C4CCCN(C4CC(C3)C)C(=O)C)C 372.60 unknown https://doi.org/10.1002/CHIN.200336165
https://doi.org/10.1016/S0040-4020(03)00545-3
https://doi.org/10.3987/COM-04-S(P)44
1-[5-[(6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl)methyl]-7-methyl-3,4,4a,5,6,7,8,8a-octahydro-2H-quinolin-1-yl]ethanone 162956423 Click to see 374.60 unknown https://doi.org/10.3987/COM-04-S(P)44
1-[5-[(6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl)methyl]-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-1-yl]ethanone 85153109 Click to see 372.60 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
https://doi.org/10.1016/S0040-4020(03)00545-3
https://doi.org/10.3987/COM-04-S(P)44
1,7-dimethyl-5-[[8-methyl-6-(piperidin-2-ylmethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-3,4,6,7,8,8a-hexahydro-2H-quinoline 74951602 Click to see 427.70 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
5-[(6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl)methyl]-1,7-dimethyl-3,4,6,7,8,8a-hexahydro-2H-quinoline 73075474 Click to see 344.60 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
https://doi.org/10.1016/S0040-4020(03)00545-3
https://doi.org/10.1016/S0040-4039(01)00688-8
https://doi.org/10.3987/COM-04-S(P)44
5-[(6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl)methyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinoline 85094434 Click to see 330.50 unknown https://doi.org/10.1016/S0040-4020(03)00545-3
5-[(6,8-dimethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl)methyl]-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinoline-1-carbaldehyde 85140460 Click to see 358.60 unknown https://doi.org/10.1016/S0040-4020(03)00545-3
7-methyl-5-[[8-methyl-6-(piperidin-2-ylmethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-1,2,3,4,6,7,8,8a-octahydroquinoline 74951523 Click to see 413.70 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
7-methyl-5-[[8-methyl-6-(piperidin-2-ylmethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methyl]-3,4,4a,5,6,7,8,8a-octahydro-2H-quinoline-1-carbaldehyde 74951601 Click to see CC1CC2CCCC(N2C(C1)CC3CCCCN3)CC4CC(CC5C4CCCN5C=O)C 443.70 unknown https://doi.org/10.1016/J.TETLET.2009.05.072
> Phenylpropanoids and polyketides / 2-arylbenzofuran flavonoids
(2R,3S,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one 10915273 Click to see 356.40 unknown via CMAUP database
(2S,3S)-2-(3,4-Dimethoxyphenyl)-2,3-dihydro-7-methoxy-3-methyl-5-benzofurancarboxaldehyde 208856 Click to see 328.40 unknown via CMAUP database
Kadsurenone 122159 Click to see 356.40 unknown via CMAUP database

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