Berberis integerrima - Unknown
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Internal ID UUID64400cc05a656334835958
Scientific name Berberis integerrima
Authority Bunge
First published in Linnaea 18: 149 (1844)

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Synonyms Top

Scientific name Authority First published in
Berberis baluchistanica Ahrendt J. Roy. Asiat. Soc. Bengal 11: 1 (1945)
Berberis densiflora Boiss. & Buhse Nouv. Mém. Soc. Imp. Naturalistes Moscou 12: 9. 1860
Berberis densiflora var. bungeana Ahrendt J. Linn. Soc., Bot. 57: 177 1961
Berberis densiflora var. macracantha Boiss. Fl. Orient. 1: 103 1867
Berberis densiflora var. macrobotrys Ahrendt J. Linn. Soc., Bot. 57: 177 1961
Berberis densiflora var. serratifolia Boiss. Fl. Orient. 1: 103 1867
Berberis turcomanica subsp. eriwanensis (Schneid.) Takht. Fl. Erevana : 60 (1972)

Common names Top

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Language Common/alternative name
Azerbaijani tamkənarlı zirinc
Russian Барбарис цельнокрайний
Chinese 全缘小檗

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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Distribution (via POWO/KEW) Top

Legend for the distribution data:
- Doubtful data
- Extinct
- Introduced
- Native
  • Asia-temperate
    • Caucasus
      • Transcaucasus
    • China
      • Xinjiang
    • Middle Asia
      • Kazakhstan
      • Kirgizstan
      • Tadzhikistan
      • Turkmenistan
      • Uzbekistan
    • Western Asia
      • Afghanistan
      • Iran
      • Iraq

Links to other databases Top

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Database ID/link to page
World Flora Online wfo-0000563334
Tropicos 100297557
KEW urn:lsid:ipni.org:names:106778-1
The Plant List kew-2673955
Open Tree Of Life 764548
Observations.org 129244
NCBI Taxonomy 1112794
IUCN Red List 133732509
IPNI 106778-1
iNaturalist 912475
GBIF 3981854
EPPO BEBIG
EOL 2880084
Elurikkus 600635
USDA GRIN 6882
CMAUP NPO2055

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
Exploring the Therapeutic Potential of Natural Products in Polycystic Ovarian Syndrome (PCOS): A Mini-Review of Lipid Profile, Blood Glucose, and Ovarian Histological Improvements Wahid S, Ramli MD, Fazleen NE, Naim RM, Mokhtar MH Life (Basel) 19-Jan-2024
PMCID:PMC10817691
doi:10.3390/life14010150
PMID:38276279
Chia (Salvia hispanica L.), a Pre-Hispanic Food in the Treatment of Diabetes Mellitus: Hypoglycemic, Antioxidant, Anti-Inflammatory, and Inhibitory Properties of α-Glucosidase and α-Amylase, and in the Prevention of Cardiovascular Disease Tavera-Hernández R, Jiménez-Estrada M, Alvarado-Sansininea JJ, Huerta-Reyes M Molecules 13-Dec-2023
PMCID:PMC10745661
doi:10.3390/molecules28248069
PMID:38138560
Effects of natural products on polycystic ovary syndrome: From traditional medicine to modern drug discovery Jung W, Choi H, Kim J, Kim J, Kim W, Nurkolis F, Kim B Heliyon 11-Oct-2023
PMCID:PMC10589870
doi:10.1016/j.heliyon.2023.e20889
PMID:37867816
Zebrafish as a robust preclinical platform for screening plant-derived drugs with anticonvulsant properties—a review Knap B, Nieoczym D, Kundap U, Kusio-Targonska K, Kukula-Koch W, Turski WA, Gawel K Front Mol Neurosci 28-Aug-2023
PMCID:PMC10493295
doi:10.3389/fnmol.2023.1221665
PMID:37701853
Iranian traditional medicinal plants for management of chronic heart failure: A review Keihanian F, Moohebati M, Saeidinia A, Mohajeri SA Medicine (Baltimore) 12-May-2023
PMCID:PMC10174410
doi:10.1097/MD.0000000000033636
PMID:37171363
Bioactive Natural Pigments’ Extraction, Isolation, and Stability in Food Applications Molina AK, Corrêa RC, Prieto MA, Pereira C, Barros L Molecules 26-Jan-2023
PMCID:PMC9920834
doi:10.3390/molecules28031200
PMID:36770869
Commodity risk assessment of Prunus persica and P. dulcis plants from Türkiye Bragard C, Baptista P, Chatzivassiliou E, Gonthier P, Jaques Miret JA, Justesen AF, MacLeod A, Magnusson CS, Milonas P, Navas‐Cortes JA, Parnell S, Potting R, Reignault PL, Stefani E, Thulke H, Van der Werf W, Civera AV, Zappalà L, Lucchi A, Gómez P, Urek G, Bernardo U, Bubici G, Carluccio AV, Chiumenti M, Di Serio F, Fanelli E, Kaczmarek A, Marzachì C, Mosbach‐Schulz O, Yuen J EFSA J 19-Jan-2023
PMCID:PMC9850261
doi:10.2903/j.efsa.2023.7735
PMID:36698493
Berberine—A Promising Therapeutic Approach to Polycystic Ovary Syndrome in Infertile/Pregnant Women Ionescu OM, Frincu F, Mehedintu A, Plotogea M, Cirstoiu M, Petca A, Varlas V, Mehedintu C Life (Basel) 02-Jan-2023
PMCID:PMC9864590
doi:10.3390/life13010125
PMID:36676074
Biochar: An emerging recipe for designing sustainable horticulture under climate change scenarios Zulfiqar F, Moosa A, Nazir MM, Ferrante A, Ashraf M, Nafees M, Chen J, Darras A, Siddique KH Front Plant Sci 05-Dec-2022
PMCID:PMC9760838
doi:10.3389/fpls.2022.1018646
PMID:36544879
Phylogeny and taxonomy of Erysiphe berberidis (s. lat.) revisited Liu L, Bradshaw M, Braun U, Götz M, Khodaparast SA, Liu TZ, Bulgakov TS, Darsaraei H, Hofbauer WK, Li Y, Liu SY Mycoscience 30-Sep-2022
PMCID:PMC10042313
doi:10.47371/mycosci.2022.07.00
PMID:37090198
Cisplatin-Induced Kidney Toxicity: Potential Roles of Major NAD+-Dependent Enzymes and Plant-Derived Natural Products Iskander A, Yan LJ Biomolecules 05-Aug-2022
PMCID:PMC9405866
doi:10.3390/biom12081078
PMID:36008971
Role of natural products towards the SARS-CoV-2: A critical review Raman K, Rajagopal K, Islam F, Dhawan M, Mitra S, Aparna B, Varakumar P, Byran G, Choudhary OP, Emran TB Ann Med Surg (Lond) 02-Jul-2022
PMCID:PMC9249430
doi:10.1016/j.amsu.2022.104062
PMID:35814035
Commodity risk assessment of Berberis thunbergii potted plants from Turkey Bragard C, Baptista P, Chatzivassiliou E, Di Serio F, Gonthier P, Jaques Miret JA, Justesen AF, MacLeod A, Magnusson CS, Milonas P, Navas‐Cortes JA, Parnell S, Reignault PL, Stefani E, Thulke H, Van der Werf W, Civera AV, Yuen J, Zappalà L, Debode J, Manceau C, Gardi C, Schulz OM, Akrivou A, Antonatos S, Beris D, Kritikos C, Kormpi M, Papachristos D, Reppa C, Potting R EFSA J 30-Jun-2022
PMCID:PMC9244780
doi:10.2903/j.efsa.2022.7392
PMID:35784819
Commodity risk assessment of Malus domestica plants from Turkey Bragard C, Baptista P, Chatzivassiliou E, Gonthier P, Jaques Miret JA, Justesen AF, MacLeod A, Magnusson CS, Milonas P, Navas‐Cortes JA, Parnell S, Potting R, Reignault PL, Stefani E, Thulke H, Van der Werf W, Civera AV, Zappalà L, Lucchi A, Gómez P, Urek G, Bernardo U, Bubici G, Carluccio AV, Chiumenti M, Di Serio F, Fanelli E, Gardi C, Marzachì C, Mosbach‐Schulz O, Yuen J EFSA J 05-May-2022
PMCID:PMC9069550
doi:10.2903/j.efsa.2022.7301
PMID:35540798
The effect of barberry (Berberis integerrima) on lipid profile and systemic inflammation in subjects with cardiovascular risk factors: a randomized controlled trial Emamat H, Zahedmehr A, Asadian S, Nasrollahzadeh J BMC Complement Med Ther 07-Mar-2022
PMCID:PMC8902769
doi:10.1186/s12906-022-03539-8
PMID:35255880

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 / Aporphines
(R)-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo(de,g)quinoline 1078819 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)OC)OC 355.40 unknown https://doi.org/10.1007/BF00630681
1,2,10-Trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-11-ol 48704 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=C3C(=C(C=C4)OC)O)OC)OC 341.40 unknown https://doi.org/10.1007/BF01374020
https://doi.org/10.1007/BF00629649
2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-1-ol 100020 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)O)OC 341.40 unknown https://doi.org/10.1007/BF01374020
https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF00631015
Glaucine 16754 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)OC)OC 355.40 unknown https://doi.org/10.1007/BF01374020
https://doi.org/10.1007/BF00630681
https://doi.org/10.1007/BF00631016
https://doi.org/10.1007/BF00631015
https://doi.org/10.1007/BF00630556
Isoboldine 133323 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)O)OC 327.40 unknown https://doi.org/10.1007/BF00631016
Isocorydine 10143 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=C3C(=C(C=C4)OC)O)OC)OC 341.40 unknown https://doi.org/10.1007/BF01374020
https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF00631016
https://doi.org/10.1007/BF00630564
Magnoflorine 73337 Click to see C[N+]1(CCC2=CC(=C(C3=C2C1CC4=C3C(=C(C=C4)OC)O)O)OC)C 342.40 unknown https://doi.org/10.1007/BF00630681
https://doi.org/10.1007/BF01134625
https://doi.org/10.1007/BF00630556
Thaliporphine 6992288 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)O)OC 341.40 unknown https://doi.org/10.1007/BF01374020
https://doi.org/10.1007/BF00630564
> Alkaloids and derivatives / Protoberberine alkaloids and derivatives
(14S)-16,17-dimethoxy-14-(trichloromethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaene 92170520 Click to see COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2C(Cl)(Cl)Cl)OCO5)OC 454.70 unknown https://doi.org/10.1007/BF01374020
(8S)-2,3,9,10-tetramethoxy-8-(trichloromethyl)-6,8-dihydro-5H-isoquinolino[2,1-b]isoquinoline 163070972 Click to see COC1=C(C2=C(C=C1)C=C3C4=CC(=C(C=C4CCN3C2C(Cl)(Cl)Cl)OC)OC)OC 470.80 unknown https://doi.org/10.1007/BF01374020
2,3,9,10-tetramethoxy-8-(trichloromethyl)-6,8-dihydro-5H-isoquinolino[2,1-b]isoquinoline 5250176 Click to see COC1=C(C2=C(C=C1)C=C3C4=CC(=C(C=C4CCN3C2C(Cl)(Cl)Cl)OC)OC)OC 470.80 unknown https://doi.org/10.1007/BF01374020
8-Trichloromethyldihydroberberine 320713 Click to see COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2C(Cl)(Cl)Cl)OCO5)OC 454.70 unknown https://doi.org/10.1007/BF01374020
Berberine 2353 Click to see COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC 336.40 unknown https://doi.org/10.1007/BF00630681
https://doi.org/10.1007/BF01134625
https://doi.org/10.1007/BF00568218
https://doi.org/10.1023/B:CONC.0000003429.41497.B6
https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF00630556
Palmatine 19009 Click to see COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC 352.40 unknown https://doi.org/10.1007/BF00629649
> Benzenoids / Benzene and substituted derivatives / Methoxybenzenes / Dimethoxybenzenes
(e)-4-(3,4-Dimethoxy-phenyl)but-3-en-1-yl palmitate 21668972 Click to see CCCCCCCCCCCCCCCC(=O)OCCC=CC1=CC(=C(C=C1)OC)OC 446.70 unknown via CMAUP database
> Lignans, neolignans and related compounds
(1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-3(36),4,6,9(35),10,12(34),18,20,22(33),24,26,31-dodecaen-6-ol 5320345 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C=C7CCN6C)OC)O3)O)OC)OC 608.70 unknown https://doi.org/10.1007/BF00630681
https://doi.org/10.1007/BF00629649
6,6',7-Trimethoxy-2,2'-dimethylberbaman-12-ol 10170 Click to see CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)O)OC 608.70 unknown https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF01374020
Berbamine 275182 Click to see CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)O)OC 608.70 unknown https://doi.org/10.1007/BF01374020
https://doi.org/10.1007/BF00630564
https://doi.org/10.1023/B:CONC.0000003429.41497.B6
https://doi.org/10.1007/BF00629649
CID 12300053 12300053 Click to see CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)O)OC 608.70 unknown https://doi.org/10.1007/BF01134625
https://doi.org/10.1007/BF00629649
Obaberine 100231 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C=C7CCN6C)OC)O3)OC)OC)OC 622.70 unknown https://doi.org/10.1007/BF00630564
Oxyacanthine 442333 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C=C7CCN6C)OC)O3)O)OC)OC 608.70 unknown https://doi.org/10.1007/BF00566827
https://doi.org/10.1023/B:CONC.0000003429.41497.B6
https://doi.org/10.1007/BF01134625
https://doi.org/10.1007/BF00630681
https://doi.org/10.1007/BF00630556
https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF00631016
https://doi.org/10.1007/BF00631015
Oxycanthine 371257 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C=C7CCN6C)OC)O3)O)OC)OC 608.70 unknown https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF00566827
https://doi.org/10.1007/BF00630681
Repandine 10031631 Click to see CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C=C7CCN6C)OC)O3)O)OC)OC 608.70 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Diterpenoids / Kaurane diterpenoids
Excisanin H 10066342 Click to see CC1(CCC(C23C1CC(C45C2CCC(C4(OC3)O)C(=C)C5=O)O)O)C 348.40 unknown https://doi.org/10.1007/BF01374020
https://doi.org/10.1007/BF00630681
https://doi.org/10.1007/BF00630556
> Lipids and lipid-like molecules / Prenol lipids / Monoterpenoids / Acyclic monoterpenoids
Citral 638011 Click to see CC(=CCCC(=CC=O)C)C 152.23 unknown via CMAUP database
Geraniol 637566 Click to see CC(=CCCC(=CCO)C)C 154.25 unknown via CMAUP database
> Lipids and lipid-like molecules / Sphingolipids / Glycosphingolipids / Simple glycosylceramides / Glycosyl-N-acylsphingosines
(2S,3R,4E,8E)-1-(beta-D-Glucopyranosyloxy)-2-[[(2R)-2-hydroxymyristoyl]amino]-4,8-octadecadiene-3-ol 10818374 Click to see CCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=CCCCCCCCCC)O)O 686.00 unknown via CMAUP database
(2S,3R,4E,8E)-1-(beta-D-Glucopyranosyloxy)-2-[[(2R)-2-hydroxypentadecanoyl]amino]-4,8-octadecadiene-3-ol 10628502 Click to see CCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=CCCCCCCCCC)O)O 700.00 unknown via CMAUP database
1-O-beta-D-Glucopyranosyl-N-[(2R)-2-hydroxypalmitoyl]sphingosine 101948670 Click to see CCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCCCCCCCCCCCC)O)O 716.00 unknown via CMAUP database
Soyacerebroside I 11104507 Click to see CCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=CCCCCCCCCC)O)O 714.00 unknown via CMAUP database
Soyacerebroside II 15599558 Click to see CCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=CCCCCCCCCC)O)O 714.00 unknown via CMAUP database
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Steroidal glycosides / Steroidal saponins
(1R,2S,4S,6R,7S,8R,9S,12S,13R,15R,16R,18S,19R)-16-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,15,19-triol 59052452 Click to see CC1C2C(CC3C2(CCC4C3CC(C5C4(CC(C(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)O)C)OC1(CCC(C)COC1C(C(C(C(O1)CO)O)O)O)O 1277.40 unknown via CMAUP database
(1R,2S,4S,6S,7S,8R,9S,12S,13R,15R,16R,18S,19R)-16-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,15,19-triol 101584207 Click to see CC1C2C(CC3C2(CCC4C3CC(C5C4(CC(C(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)O)C)OC1(CCC(C)COC1C(C(C(C(O1)CO)O)O)O)O 1277.40 unknown via CMAUP database
(1S,2S,4S,6R,7S,8R,9S,12S,13R,15R,16R,18R)-16-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,15,18-triol 59052451 Click to see CC1C2C(CC3C2(CCC4C3CCC5(C4(CC(C(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)O)C)OC1(CCC(C)COC1C(C(C(C(O1)CO)O)O)O)O 1277.40 unknown via CMAUP database
(1S,2S,4S,6R,7S,8R,9S,12S,13R,15R,16R,18R)-16-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,15,18-triol 59052312 Click to see CC1C2C(CC3C2(CCC4C3CCC5(C4(CC(C(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O)C)O)C)OC1(CCC(C)COC1C(C(C(C(O1)CO)O)O)O)O 1439.50 unknown via CMAUP database
(1S,2S,4S,6S,7S,8R,9S,12S,13R,15R,16R,18R)-16-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,15,18-triol 101584206 Click to see CC1C2C(CC3C2(CCC4C3CCC5(C4(CC(C(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)O)C)OC1(CCC(C)COC1C(C(C(C(O1)CO)O)O)O)O 1277.40 unknown via CMAUP database
(1S,2S,4S,6S,7S,8R,9S,12S,13R,15R,16R,18R)-16-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,15,18-triol 101584205 Click to see CC1C2C(CC3C2(CCC4C3CCC5(C4(CC(C(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O)C)O)C)OC1(CCC(C)COC1C(C(C(C(O1)CO)O)O)O)O 1439.50 unknown via CMAUP database
(25R)-3beta-[[4-O-[2-O,3-O-Bis(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]-beta-D-galactopyranosyl]oxy]-5alpha-spirostan-2alpha-ol 101932450 Click to see CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CC(C(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(C(O9)CO)O)O)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)C)C)C)OC1 1081.20 unknown via CMAUP database
(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 101826551 Click to see CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(CO9)O)O)O)OC2C(C(C(C(O2)CO)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)C)C)C)OC1 1197.30 unknown via CMAUP database
Eruboside B 13787750 Click to see CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC(C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(C(O9)CO)O)O)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)C)O)C)C)OC1 1081.20 unknown via CMAUP database
> Nucleosides, nucleotides, and analogues / Purine nucleosides
Adenosine 60961 Click to see C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N 267.24 unknown via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acids / L-alpha-amino acids
(2R)-2-amino-3-[(R)-prop-2-enylsulfinyl]propanoic acid 51399534 Click to see C=CCS(=O)CC(C(=O)O)N 177.22 unknown via CMAUP database
(2R)-2-ammonio-3-(methylselanyl)propanoate 45266674 Click to see C[Se]CC(C(=O)[O-])[NH3+] 182.09 unknown via CMAUP database
(2R)-2-azaniumyl-3-[(S)-methylsulfinyl]propanoate 40528043 Click to see CS(=O)CC(C(=O)[O-])[NH3+] 151.19 unknown via CMAUP database
L-selenomethionine 105024 Click to see C[Se]CCC(C(=O)O)N 196.12 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
gamma-Glutamylphenylalanine 111299 Click to see C1=CC=C(C=C1)CC(C(=O)O)NC(=O)CCC(C(=O)O)N 294.30 unknown via CMAUP database
Phenylalanine 6140 Click to see C1=CC=C(C=C1)CC(C(=O)O)N 165.19 unknown via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Cysteine and derivatives / L-cysteine-S-conjugates
(2R)-2-azaniumyl-3-[(prop-2-en-1-yl)sulfanyl]propanoate 40424388 Click to see C=CCSCC(C(=O)[O-])[NH3+] 161.22 unknown via CMAUP database
(2R)-2-azaniumyl-3-propylsulfanylpropanoate 40565896 Click to see CCCSCC(C(=O)[O-])[NH3+] 163.24 unknown via CMAUP database
s-Allylmercaptocysteine 9794159 Click to see C=CCSSCC(C(=O)O)N 193.30 unknown via CMAUP database
S-Methylthiocysteine 3080775 Click to see CSSCC(C(=O)O)N 167.30 unknown via CMAUP database
S-trans-1-propenyl-L-cysteine 91820358 Click to see CC=CSCC(C(=O)[O-])[NH3+] 161.22 unknown via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Peptides / Dipeptides
gamma-GLUTAMYL-S-ALLYLCYSTEINE 11346811 Click to see C=CCSCC(C(=O)O)NC(=O)CCC(C(=O)O)N 290.34 unknown via CMAUP database
gamma-glutamyl-S-allylmercaptocysteine 101630431 Click to see C=CCSSCC(C(=O)O)NC(=O)CCC(C(=O)O)N 322.40 unknown via CMAUP database
gamma-glutamyl-S-propyl cysteine 54090099 Click to see CCCSCC(C(=O)O)NC(=O)CCC(C(=O)O)N 292.35 unknown via CMAUP database
Methylseleno carboxyethylglutamine 20807051 Click to see C[Se]CC(C(=O)O)NC(=O)CCC(C(=O)O)N 311.20 unknown via CMAUP database
Methylseleno carboxypropylglutamine 16128830 Click to see C[Se]CCC(C(=O)O)NC(=O)CCC(C(=O)O)N 325.23 unknown via CMAUP database
N-gamma-Glutamyl-S-trans-(1-propenyl)cysteine 87289205 Click to see CC=CSCC(C(=O)O)NC(=O)CCC(C(=O)O)N 290.34 unknown via CMAUP database
N5-((R)-1-Carboxy-3-(methylthio)propyl)-L-glutamine 87315837 Click to see CSCCC(C(=O)O)NC(=O)CCC(C(=O)O)N 278.33 unknown via CMAUP database
> Organic acids and derivatives / Organic sulfuric acids and derivatives / Sulfuric acid esters / Sulfuric acid diesters
(E)-2-Propenyl [3-(2-propenylthio)-2-propenyl] sulfate 10977885 Click to see C=CCOS(=O)(=O)OCC=CSCC=C 250.30 unknown via CMAUP database
> Organic acids and derivatives / Organic thiosulfuric acids and derivatives / S-alkyl thiosulfates
3-Sulfonatosulfanylprop-1-ene 59479946 Click to see C=CCSS(=O)(=O)[O-] 153.20 unknown via CMAUP database
> Organic acids and derivatives / Thiosulfinic acid esters
3-[(S)-prop-2-enylsulfinyl]sulfanylprop-1-ene 51380898 Click to see C=CCSS(=O)CC=C 162.30 unknown via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Alcohols and polyols / Primary alcohols
Allyl alcohol 7858 Click to see C=CCO 58.08 unknown via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Glycosyl compounds / Phenolic glycosides
Eugenol gentiobioside 10390778 Click to see COC1=C(C=CC(=C1)CC=C)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O 488.50 unknown via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Carbonyl compounds / Aldehydes / Alpha-hydrogen aldehydes
Valeraldehyde 8063 Click to see CCCCC=O 86.13 unknown via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Carbonyl compounds / Alpha,beta-unsaturated aldehydes / Enals
(E)-3-(prop-2-enyldisulfanyl)prop-2-enal 5317516 Click to see C=CCSSC=CC=O 160.30 unknown via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Enols
Propen-2-ol 141483 Click to see CC(=C)O 58.08 unknown via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Ethers / Diarylethers
(1S,13R)-19,20,24-trimethoxy-14,29-dimethyl-7,22-dioxa-14,29-diazaheptacyclo[21.6.2.23,6.28,11.113,17.026,30.021,32]hexatriaconta-3(36),4,6(35),8(34),9,11(33),17,19,21(32),23,25,30-dodecaene 163042492 Click to see CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=CC=C(CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)C=C5)OC 592.70 unknown https://doi.org/10.1007/BF00566827
19,20,24-Trimethoxy-14,29-dimethyl-7,22-dioxa-14,29-diazaheptacyclo[21.6.2.23,6.28,11.113,17.026,30.021,32]hexatriaconta-3(36),4,6(35),8(34),9,11(33),17,19,21(32),23,25,30-dodecaene 163042491 Click to see CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=CC=C(CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)C=C5)OC 592.70 unknown https://doi.org/10.1007/BF00566827
> Organoheterocyclic compounds / Diazines / Pyrimidines and pyrimidine derivatives / Aminopyrimidines and derivatives
N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(Z)-5-hydroxy-3-(prop-2-enyldisulfanyl)pent-2-en-2-yl]formamide 3037212 Click to see CC1=NC=C(C(=N1)N)CN(C=O)C(=C(CCO)SSCC=C)C 354.50 unknown via CMAUP database
> Organoheterocyclic compounds / Dihydrofurans / Furanones / Butenolides
2(5H)-Furanone, 4-bromo-5-(bromomethylene)-, (5Z)- 10131246 Click to see C1=C(C(=CBr)OC1=O)Br 253.88 unknown via CMAUP database
> Organoheterocyclic compounds / Dithioles / 1,2-dithioles
4-Methyl-1,2-dithiacyclopentene 5319597 Click to see CC1=CSSC1 118.20 unknown via CMAUP database
5-Methyl-3H-1,2-dithiol 5319596 Click to see CC1=CCSS1 118.20 unknown via CMAUP database
> Organoheterocyclic compounds / Isoquinolines and derivatives / Benzylisoquinolines
(-)-Armepavine 442169 Click to see CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)OC)OC 313.40 unknown https://doi.org/10.1007/BF01374020
https://doi.org/10.1007/BF00631016
https://doi.org/10.1007/BF00631020
(1S)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium-8-ol 173713 Click to see C[N+]1(CCC2=C(C1CC3=CC=C(C=C3)O)C(=C(C=C2)OC)O)C 314.40 unknown https://doi.org/10.1007/BF00570225
(R)-Reticuline 440586 Click to see CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)O)O)OC 329.40 unknown https://doi.org/10.1007/BF00629649
2-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 1377255 Click to see COC1=C(C=C(C=C1)CN2CCC3=CC(=C(C=C3C2)OC)OC)OC 343.40 unknown https://doi.org/10.1007/BF00631020
https://doi.org/10.1007/BF00631016
3,4-Dimethoxy-2-[(5-oxo-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-yl)methyl]benzoic acid 21769964 Click to see COC1=C(C(=C(C=C1)C(=O)O)CN2CCC3=CC4=C(C=C3C2=O)OCO4)OC 385.40 unknown https://doi.org/10.1007/BF00631015
Armepavine 98348 Click to see CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)OC)OC 313.40 unknown https://doi.org/10.1007/BF01374020
Reticulin 10233 Click to see CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)O)O)OC 329.40 unknown https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF00631016
Reticuline 439653 Click to see CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)O)O)OC 329.40 unknown https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF00631020
https://doi.org/10.1007/BF00631016
https://doi.org/10.1007/BF00630564
> Organoheterocyclic compounds / Isoquinolines and derivatives / Isoquinolones and derivatives
2,9,10-Trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-3-one 10065647 Click to see COC1=C(C2=CN3CCC4=CC(=O)C(=CC4=C3C=C2C=C1)OC)OC 337.40 unknown https://doi.org/10.1007/BF00629649
https://doi.org/10.1007/BF00630564
6-(6,7-dimethoxy-3-oxo-1H-2-benzofuran-1-yl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-one 322371 Click to see COC1=C(C2=C(C=C1)C(=O)OC2N3CCC4=CC5=C(C=C4C3=O)OCO5)OC 383.40 unknown https://doi.org/10.1007/BF00629649
6-[(1S)-6,7-dimethoxy-3-oxo-1H-2-benzofuran-1-yl]-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-one 163022273 Click to see COC1=C(C2=C(C=C1)C(=O)OC2N3CCC4=CC5=C(C=C4C3=O)OCO5)OC 383.40 unknown https://doi.org/10.1007/BF00629649
6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 610097 Click to see COC1=C(C=C2C(=C1)CCNC2=O)OC 207.23 unknown https://doi.org/10.1021/NP50022A001
> Organoheterocyclic compounds / Pyrans / Pyranones and derivatives
Allixin 86374 Click to see CCCCCC1=C(C(=O)C(=C(O1)C)OC)O 226.27 unknown via CMAUP database
> Organoheterocyclic compounds / Tetrahydroisoquinolines
2-(1,3-benzodioxol-5-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline 751377 Click to see COC1=C(C=C2CN(CCC2=C1)CC3=CC4=C(C=C3)OCO4)OC 327.40 unknown https://doi.org/10.1007/BF00631020
https://doi.org/10.1007/BF00631016
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline 15623 Click to see COC1=C(C=C2CNCCC2=C1)OC 193.24 unknown https://doi.org/10.1007/BF00631016
Isocorypalline 2752173 Click to see CN1CCC2=CC(=C(C=C2C1)OC)O 193.24 unknown https://doi.org/10.1007/BF00566827
> Organosulfur compounds / Allyl sulfur compounds
(E)-1-Propenyl 2-propenyl disulfide 5352907 Click to see CC=CSSCC=C 146.30 unknown via CMAUP database
Allyl methyl disulfide 62434 Click to see CSSCC=C 120.20 unknown via CMAUP database
Allyl methyl sulfide 66282 Click to see CSCC=C 88.17 unknown via CMAUP database
Allyl methyl tetrasulfide 525329 Click to see CSSSSCC=C 184.40 unknown via CMAUP database
Allyl prop-1-enyl disulfide 5352855 Click to see CC=CSSCC=C 146.30 unknown via CMAUP database
Allyl propyl disulfide 16591 Click to see CCCSSCC=C 148.30 unknown via CMAUP database
Diallyl disulfide 16590 Click to see C=CCSSCC=C 146.30 unknown via CMAUP database
Diallyl sulfide 11617 Click to see C=CCSCC=C 114.21 unknown via CMAUP database
Diallyl tetrasulfide 75552 Click to see C=CCSSSSCC=C 210.40 unknown via CMAUP database
Methyl 2-propenyl pentasulfide 528713 Click to see CSSSSSCC=C 216.40 unknown via CMAUP database
> Organosulfur compounds / Organic disulfides / Dialkyldisulfides
Dimethyl Disulfide 12232 Click to see CSSC 94.20 unknown via CMAUP database
Dipropyl disulfide 12377 Click to see CCCSSCCC 150.30 unknown via CMAUP database
Methyl propyl disulfide 16592 Click to see CCCSSC 122.30 unknown via CMAUP database
> Organosulfur compounds / Organic trisulfides
6-ethenyl-4H-trithiine 5315241 Click to see C=CC1=CCSSS1 162.30 unknown via CMAUP database
Allyl methyl trisulfide 61926 Click to see CSSSCC=C 152.30 unknown via CMAUP database
Diallyl trisulfide 16315 Click to see C=CCSSSCC=C 178.30 unknown via CMAUP database
Dimethyl trisulfide 19310 Click to see CSSSC 126.30 unknown via CMAUP database
Methyl propyl trisulfide 5319765 Click to see CCCSSSC 154.30 unknown via CMAUP database
> Organosulfur compounds / Sulfonyls
S-2-Propenyl 2-propene-1-sulfonothioate 85776791 Click to see C=CCSS(=O)(=O)CC=C 178.30 unknown via CMAUP database
> Organosulfur compounds / Sulfonyls / Sulfones
(E)-3-(prop-2-enyldisulfanyl)-1-prop-2-enylsulfonylprop-1-ene 5322033 Click to see C=CCSSCC=CS(=O)(=O)CC=C 250.40 unknown via CMAUP database
> Organosulfur compounds / Sulfoxides
(E)-1-(prop-2-enyldisulfanyl)-3-[(R)-prop-2-enylsulfinyl]prop-1-ene 76962524 Click to see C=CCSSC=CCS(=O)CC=C 234.40 unknown via CMAUP database
(Z)-1-(prop-2-enyldisulfanyl)-3-[(R)-prop-2-enylsulfinyl]prop-1-ene 76960957 Click to see C=CCSSC=CCS(=O)CC=C 234.40 unknown via CMAUP database
> Organosulfur compounds / Thioacetals / Dithioacetals
1,3-Dithiole 5316944 Click to see C1SC=CS1 104.20 unknown via CMAUP database
> Organosulfur compounds / Thioethers / Dialkylthioethers
Dimethyl sulfide 1068 Click to see CSC 62.14 unknown via CMAUP database
> Organosulfur compounds / Thioethers / Thioenol ethers
Divinyl sulfide 12321 Click to see C=CSC=C 86.16 unknown via CMAUP database
> Phenylpropanoids and polyketides / Anthracyclines
(1S,11R,12R,13R,21S,22S,23R,24S)-13-(4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl)oxy-23-(dimethylamino)-11,15,22,24-tetrahydroxy-12-methoxy-1,11-dimethyl-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2(19),3,5(18),7(16),8,14-hexaene-6,17-dione 139587745 Click to see CC1C(C(C(C(O1)OC2C(C(CC3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC6=C5OC7C(C(C(C6(O7)C)O)N(C)C)O)(C)O)OC)OC)(C)O)O 715.70 unknown https://doi.org/10.1007/BF00629649
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid O-glycosides / Flavonoid-3-O-glycosides
delphinidin 3-O-beta-D-glucoside betaine 165559 Click to see C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=O)C=C3O2)O)OC4C(C(C(C(O4)CO)O)O)O 464.40 unknown https://doi.org/10.1007/BF00579163

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