Peganum harmala - Unknown
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Details Top

Internal ID UUID6440012a04ea9502429089
Scientific name Peganum harmala
Authority L.
First published in Sp. Pl. : 444 (1753)

Description Top

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Synonyms Top

Scientific name Authority First published in
Mesembryanthemum caspicum S.G.Gmel. Reise Russland (S.G.Gmel.) 4: 48. 1784 ; ex Ledeb. Fl. Ross. i. 490
Peganon harmalum (L.) St.-Lag. Ann. Soc. Bot. Lyon vii. (1880) 131.
Peganum rothschildianum Buxb. Verh. Zool.-Bot. Ges. Wien 76: 54 (1926 publ. 1927)
Harmala multifida All. Fl. Pedem. 2: 101 (1785)
Harmala peganum Crantz Inst. Rei Herb. 2: 463 (1766)
Harmala syriaca Bubani Fl. Pyren. 3: 354 (1901)
Malacocarpus crithmifolius Fisch. & C.A.Mey. Index Seminum [St.Petersburg (Petropolitanus)] ix. 79 (1843).
Peganum crithmifolium Retz. Observ. Bot. 3: 34 (1783)

Common names Top

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Language Common/alternative name
English syrian rue
English harmal
English african rue
English esfand
English wild rue
English harmal peganum
Spanish matarrocin
Spanish matarocín
Spanish matarocin
Spanish jamega
Spanish harmel
Spanish hármala
Spanish harmaga real
Spanish harmaga blanca
Spanish hármaga
Spanish harmaga
Spanish estacarracín
Spanish gamarsa
Spanish estacarracin
Spanish matarrocín
Spanish matarrufin
Spanish matarrufín
Spanish ruda borda
Spanish ruda harmala
Spanish ruda hármala
Spanish ruda siria
Spanish ruda-harmala
Spanish ruda-harmel
Spanish tacarrecin
Spanish tacarrecín
Spanish venenera
Spanish catarrucín
Spanish harmala
Spanish alargama
Spanish alárgama
Spanish alfarma
Spanish alfarmega
Spanish alfármega
Spanish alhamega
Spanish alhargama
Spanish alharma
Spanish alharmaga
Spanish alhármaga
Spanish alharmega
Spanish alhármega
Spanish alhármel
Spanish aljamega
Spanish arjamega
Spanish armala
Spanish armalá
Spanish catarrecino
Spanish catarrocin
Spanish catarrocín
Spanish catarrofic
Spanish catarrofin
Spanish catarrucin
Spanish cuentas de burro
Spanish alharmel
ang armélu
Arabic حرمل شائع
Azerbaijani Üzərlik
azb اوزرلیک
Bulgarian зърнеш
Catalan harmala
Catalan harmalà
German steppenraute
Persian اسفند
Persian اسپند
Persian دونشت
Finnish pilviharmikki
Finnish syyrianängelmä
French harmal
French rue de syrie
Hebrew שבר לבן
Upper Sorbian harmalowy rutownik
Hungarian törökpirosító
Hungarian szíriai rutafű
Armenian Սպանդ սովորական
Japanese ペガヌム・ハルマラ
Japanese シリアン・ルー
Kabyle lḥarmel
Kazakh Адыраспан
Kazakh Кәдімгі адыраспан
ku Ûzelg
Latvian harmala
Macedonian диво седефче
Malayalam ഹർമാൽ
mzn اسپند
Polish poganek rutowaty
Polish ruta stepowa
Polish pergamum harmala
Russian Гармала обыкновенная
Swedish harmelbuske
tg Испанд
Turkish Üzerlik
Urdu ہرمل
Chinese 臭古朵
Chinese 骆驼蓬
Chinese 骆驼蓬子

Subspecies (abbr. subsp./ssp.) Top

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No subspecies added yet.

Varieties (abbr. var.) Top

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Name Authority First published in
Peganum harmala var. grandiflorum Hadidi Fl. Iranica 98: 20 (1972)

Subvarieties (abbr. subvar.) Top

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No subvariety added yet.

Forms (abbr. f.) Top

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Germination/Propagation Top

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Sow seeds at 20°C, expecting germination within 3 months without further temperature treatment.
Requires Light or Surface Sowing: These seeds need light to germinate and should not be covered with soil or only very lightly. They are often very small and sown directly on the surface of the growing medium.
delay pricking out seedlings

Distribution (via POWO/KEW) Top

Legend for the distribution data:
- Doubtful data
- Extinct
- Introduced
- Native
  • Africa
    • Northern Africa
      • Algeria
      • Egypt
      • Libya
      • Morocco
      • Tunisia
    • Southern Africa
      • Cape Provinces
  • Asia-temperate
    • Arabian Peninsula
      • Kuwait
      • Saudi Arabia
      • Yemen
    • Caucasus
      • North Caucasus
      • Transcaucasus
    • China
      • China North-central
      • Inner Mongolia
      • Qinghai
      • Tibet
      • Xinjiang
    • Middle Asia
      • Kazakhstan
      • Kirgizstan
      • Tadzhikistan
      • Turkmenistan
      • Uzbekistan
    • Mongolia
      • Mongolia
    • Siberia
      • Tuva
    • Western Asia
      • Afghanistan
      • Cyprus
      • East Aegean Islands
      • Iran
      • Iraq
      • Lebanon-Syria
      • Palestine
      • Sinai
      • Turkey
  • Asia-tropical
    • Indian Subcontinent
      • Bangladesh
      • India
      • Pakistan
      • West Himalaya
  • Europe
    • Eastern Europe
      • East European Russia
      • Krym
      • South European Russia
      • Ukraine
    • Middle Europe
      • Hungary
    • Southeastern Europe
      • Bulgaria
      • Greece
      • Italy
      • Romania
      • Turkey-in-Europe
      • Yugoslavia
    • Southwestern Europe
      • France
      • Sardegna
      • Spain
  • Northern America
    • Northwestern U.S.A.
      • Colorado
    • South-central U.S.A.
      • New Mexico
      • Texas
    • Southwestern U.S.A.
      • Nevada

Links to other databases Top

Suggest others/fix!
Database ID/link to page
World Flora Online wfo-0000474572
UNII Z7Q8PX8X4Z
USDA Plants PEHA
Tropicos 34600013
INPN 112628
Flora of Italy 2854
KEW urn:lsid:ipni.org:names:774545-1
The Plant List kew-2548698
Open Tree Of Life 461719
Observations.org 127600
NCBI Taxonomy 43879
Nature Serve 2.135419
IPNI 774545-1
iNaturalist 78374
GBIF 3189912
Freebase /m/03pd1c
EPPO PEGHA
EOL 581852
Elurikkus 374218
Calflora (Californian flora) 8761
USDA GRIN 27098
Wikipedia Peganum_harmala
CMAUP NPO1085

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
Ethnobotanical survey on herbal remedies for the management of type 2 diabetes in the Casablanca-Settat region, Morocco Arraji M, Al Wachami N, Boumendil K, Chebabe M, Mochhoury L, Laamiri FZ, Barkaoui M, Chahboune M BMC Complement Med Ther 15-Apr-2024
PMCID:PMC11017650
doi:10.1186/s12906-024-04468-4
PMID:38622669
A dataset for fine-grained seed recognition Yuan M, Lv N, Dong Y, Hu X, Lu F, Zhan K, Shen J, Wu X, Zhu L, Xie Y Sci Data 06-Apr-2024
PMCID:PMC10998916
doi:10.1038/s41597-024-03176-5
PMID:38582756
Cross-cultural ethnobotany of the Baltis and Shinas in the Kharmang district, Trans-Himalaya India-Pakistan border Hussain B, Abbas Z, Alam J, Harun N, Khan SM, Ahmad Z, Han H, Yoo S, Raposo A Heliyon 27-Mar-2024
PMCID:PMC10998220
doi:10.1016/j.heliyon.2024.e28613
PMID:38586350
UPLC-TQD-MS/MS Method Validation for Quality Control of Alkaloid Content in Lepidium meyenii (Maca)-Containing Food and Dietary Supplements Le NT, Foubert K, Theunis M, Naessens T, Bozdag M, Van Der Veken P, Pieters L, Tuenter E ACS Omega 26-Mar-2024
PMCID:PMC11007719
doi:10.1021/acsomega.3c09356
PMID:38617670
Harmaline induces apoptosis and inhibits migration in A2780 ovarian cancer cells in vitro Shariat Razavi SA, Taghdisi Khaboushan M, Jafari R, Shahini A, Ferns GA, Bahrami A Physiol Rep 26-Mar-2024
PMCID:PMC10965315
doi:10.14814/phy2.15984
PMID:38531560
Research progress on the antitumor effects of harmine Hu Y, Yu X, Yang L, Xue G, Wei Q, Han Z, Chen H Front Oncol 25-Mar-2024
PMCID:PMC10999596
doi:10.3389/fonc.2024.1382142
PMID:38590646
Enhancing Native Plant Establishment in Mine Tailings under Drought Stress Conditions through the Application of Organo-Mineral Amendments and Microbial Inoculants Atika M, Leila B, Pereira SI, Castro PM, Ali B Plants (Basel) 17-Mar-2024
PMCID:PMC10975093
doi:10.3390/plants13060863
PMID:38592869
Folk Knowledge and Perceptions about the Use of Wild Fruits and Vegetables–Cross-Cultural Knowledge in the Pipli Pahar Reserved Forest of Okara, Pakistan Jabeen S, Arshad F, Harun N, Waheed M, Alamri S, Haq SM, Vitasović-Kosić I, Fatima K, Chaudhry AS, Bussmann RW Plants (Basel) 14-Mar-2024
PMCID:PMC10974405
doi:10.3390/plants13060832
PMID:38592859
A decade of advances in the study of buckwheat for organic farming and agroecology (2013-2023) Vieites-Álvarez Y, Reigosa MJ, Sánchez-Moreiras AM Front Plant Sci 06-Mar-2024
PMCID:PMC10950947
doi:10.3389/fpls.2024.1354672
PMID:38510443
Syrupy herbal formulation of green bean pod extract of Phaseolus vulgaris L.: Formulation optimization by central composite design, and evaluation for anti-urolithiatic activity Noorulla KM, Doyo Dalecha D, Jemal Haji M, S R, Arumugam M, Zafar A, Gadisa Gobena W, Mekit S, Haji Negawo H, Hussein M, Fekadu Demessie H, Yasir M Heliyon 29-Feb-2024
PMCID:PMC10943400
doi:10.1016/j.heliyon.2024.e27330
PMID:38495171
The mechanistic role of natural antimicrobials in preventing Staphylococcus aureus invasion of MAC-T cells using an in vitro mastitis model Balta I, McCleery D, David SR, Pet E, Stef D, Iancu T, Pet I, Stef L, Corcionivoschi N Ir Vet J 27-Feb-2024
PMCID:PMC10898119
doi:10.1186/s13620-024-00265-0
PMID:38414081
The sustainable use of diverse plants accustomed by different ethnic groups in Sibi District, Balochistan, Pakistan Maria B, Saeed S, Ahmed A, Ahmed M, Rehman A PLoS One 21-Feb-2024
PMCID:PMC10880983
doi:10.1371/journal.pone.0294989
PMID:38381718
Anti-Bacterial Activity of Green Synthesised Silver and Zinc Oxide Nanoparticles against Propionibacterium acnes Al-Momani H, Massadeh MI, Almasri M, Al Balawi D, Aolymat I, Hamed S, Albiss BA, Ibrahim L, Balawi HA, Al Haj Mahmoud S Pharmaceuticals (Basel) 16-Feb-2024
PMCID:PMC10891609
doi:10.3390/ph17020255
PMID:38399471
The Contribution of Botanical Origin to the Physicochemical and Antioxidant Properties of Algerian Honeys Harbane S, Escuredo O, Saker Y, Ghorab A, Nakib R, Rodríguez-Flores MS, Ouelhadj A, Seijo MC Foods 14-Feb-2024
PMCID:PMC10888090
doi:10.3390/foods13040573
PMID:38397550
Exploring the benefits of wild plants in dietary nutrition: investigating perspectives, choices, health impacts and sustainable practices Anwar T, Qureshi H, Shahzadi S, Siddiqi EH, Ali HM, Abdelhamid MM, Nazim M BMC Complement Med Ther 14-Feb-2024
PMCID:PMC10865668
doi:10.1186/s12906-024-04379-4
PMID:38355544

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 / Harmala alkaloids
(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol 163190288 Click to see CC1=NCCC2=C1NC3=C2C=CC(=C3OC4C(C(C(C(O4)CO)O)O)O)OC 392.40 unknown https://doi.org/10.1016/0031-9422(75)85054-0
(R)-Tetrahydroharmine 442118 Click to see CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC 216.28 unknown via CMAUP database
1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-7-one 5353656 Click to see CC1=C2C(=C3C=CC(=O)C=C3N2)CCN1 200.24 unknown https://doi.org/10.1016/J.FITOTE.2010.04.004
2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol 162966983 Click to see CC1=NCCC2=C1NC3=C2C=CC(=C3OC4C(C(C(C(O4)CO)O)O)O)OC 392.40 unknown https://doi.org/10.1016/0031-9422(75)85054-0
6-Methoxyharman 5376026 Click to see CC1=NC=CC2=C1NC3=C2C=C(C=C3)OC 212.25 unknown https://doi.org/10.1016/0031-9422(91)85312-N
7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole 5280951 Click to see CC1=C2C(=C3C=CC(=CC3=N2)OC)CCN1 214.26 unknown https://doi.org/10.1016/J.FITOTE.2010.04.004
7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carbaldehyde 163192349 Click to see COC1=CC2=C(C=C1)C3=C(N2)C(NCC3)C=O 230.26 unknown https://doi.org/10.3987/COM-88-4490
Harmalan 160510 Click to see CC1=NCCC2=C1NC3=CC=CC=C23 184.24 unknown https://www.ncbi.nlm.nih.gov/pmc/articles/PMC426218/
Harmaline 3564 Click to see CC1=NCCC2=C1NC3=C2C=CC(=C3)OC 214.26 unknown https://doi.org/10.1111/J.1439-0418.1997.TB01387.X
https://doi.org/10.1007/BF00563655
https://doi.org/10.1007/BF00565223
https://doi.org/10.1016/S0031-9422(00)97911-1
https://doi.org/10.1007/BF00579504
https://doi.org/10.1515/ZNC-1992-3-410
https://doi.org/10.1002/PCA.2800060206
https://doi.org/10.1016/0031-9422(93)85453-X
https://doi.org/10.1351/PAC196306040601
https://doi.org/10.1007/BF00569029
https://doi.org/10.1016/S0031-9422(00)81861-0
https://doi.org/10.1007/S10600-006-0085-7
https://doi.org/10.1016/0031-9422(91)85312-N
https://doi.org/10.1021/NP50018A025
Harmalol 3565 Click to see CC1=NCCC2=C1NC3=C2C=CC(=C3)O 200.24 unknown https://doi.org/10.1007/S10600-006-0085-7
https://doi.org/10.1016/0031-9422(93)85453-X
https://doi.org/10.1016/S0031-9422(00)97911-1
https://doi.org/10.1351/PAC196306040601
https://doi.org/10.1515/ZNC-1992-3-410
https://doi.org/10.1111/J.1439-0418.1997.TB01387.X
https://doi.org/10.1016/0031-9422(91)85312-N
https://doi.org/10.1515/ZNC-1990-0626
https://doi.org/10.1007/BF00563655
Harman 5281404 Click to see CC1=NC=CC2=C1NC3=CC=CC=C23 182.22 unknown https://doi.org/10.1016/J.FITOTE.2010.04.004
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC426218/
Harmine 5280953 Click to see CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC 212.25 unknown https://doi.org/10.1016/S0031-9422(00)81861-0
https://doi.org/10.1007/S10600-009-9381-3
https://doi.org/10.1007/BF00563370
https://doi.org/10.1007/BF00564251
https://doi.org/10.1007/BF00579504
https://doi.org/10.1515/ZNC-1990-0626
https://doi.org/10.1007/BF00563655
https://doi.org/10.1016/0031-9422(93)85453-X
https://doi.org/10.1016/S0031-9422(00)86329-3
https://doi.org/10.1016/0031-9422(91)85312-N
https://doi.org/10.1007/BF00567834
https://doi.org/10.1007/BF00569029
https://doi.org/10.1351/PAC196306040601
https://doi.org/10.1016/J.FITOTE.2010.04.004
https://doi.org/10.1007/S10600-006-0085-7
https://doi.org/10.1021/NP50018A025
https://doi.org/10.1007/BF00565223
https://doi.org/10.1111/J.1439-0418.1997.TB01387.X
https://doi.org/10.1016/S0031-9422(00)97911-1
https://doi.org/10.1515/ZNC-1992-3-410
Harmine C-11 5462124 Click to see CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC 211.25 unknown via CMAUP database
Harmol 68094 Click to see CC1=C2C(=C3C=CC(=O)C=C3N2)C=CN1 198.22 unknown https://doi.org/10.1016/0031-9422(93)85453-X
https://doi.org/10.1515/ZNC-1992-3-410
https://doi.org/10.1007/BF00563655
Tetrahydroharmine 159809 Click to see CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC 216.28 unknown https://doi.org/10.1007/BF00563655
Tetrahydroharmol 368982 Click to see CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)O 202.25 unknown via CMAUP database
> Benzenoids / Benzene and substituted derivatives / Aniline and substituted anilines
(3R)-1-[(2-aminophenyl)methyl]-3-hydroxypyrrolidin-2-one 92470596 Click to see C1CN(C(=O)C1O)CC2=CC=CC=C2N 206.24 unknown https://doi.org/10.1007/BF00596685
> Benzenoids / Phenanthrenes and derivatives
Phenanthrene 995 Click to see C1=CC=C2C(=C1)C=CC3=CC=CC=C32 178.23 unknown via CMAUP database
> Lignans, neolignans and related compounds / Lignan lactones
(5R,5Ar)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one 10452586 Click to see COC1=CC(=CC(=C1O)OC)C2C3C(CC4=CC5=C(C=C24)OCO5)COC3=O 384.40 unknown via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty acids and conjugates / Long-chain fatty acids
(9R,14S)-9,14-dihydroxyoctadecanoic acid 163056343 Click to see CCCCC(CCCCC(CCCCCCCC(=O)O)O)O 316.50 unknown https://doi.org/10.1016/0031-9422(71)85084-7
9,14-Dihydroxyoctadecanoic acid 5312768 Click to see CCCCC(CCCCC(CCCCCCCC(=O)O)O)O 316.50 unknown https://doi.org/10.1016/0031-9422(71)85084-7
> Lipids and lipid-like molecules / Fatty Acyls / Fatty alcohols
1-Hexacosanol 68171 Click to see CCCCCCCCCCCCCCCCCCCCCCCCCCO 382.70 unknown https://doi.org/10.1007/S10600-006-0086-6
1-Nonacosanol 243696 Click to see CCCCCCCCCCCCCCCCCCCCCCCCCCCCCO 424.80 unknown https://doi.org/10.1007/S10600-006-0086-6
> Lipids and lipid-like molecules / Fatty Acyls / Lineolic acids and derivatives
Linoleic Acid 5280450 Click to see CCCCCC=CCC=CCCCCCCCC(=O)O 280.40 unknown https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7997936/
> Lipids and lipid-like molecules / Prenol lipids / Sesquiterpenoids / Guaianes
2-[(8S)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoic acid 5321022 Click to see CC1CCC(CC2=C(C(=O)CC12)C)C(=C)C(=O)O 248.32 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Terpene glycosides / Iridoid O-glycosides
[5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl]methyl acetate 5317967 Click to see CC(=O)OCC1CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O 390.40 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Terpene glycosides / Triterpene glycosides / Triterpene saponins
Pedunculoside 14286954 Click to see CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)O)C)C)C2C1(C)O)C)C(=O)OC6C(C(C(C(O6)CO)O)O)O 650.80 unknown via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Triterpenoids
(10S,13R,14R)-4,4,10,13,14-pentamethyl-17-(6-methylhept-5-en-2-yl)-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol 44135612 Click to see CC(CCC=C(C)C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C 426.70 unknown via CMAUP database
> Lipids and lipid-like molecules / Steroids and steroid derivatives / Steroidal alkaloids / Cerveratrum-type alkaloids
6,10,23-Trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosane-10,17,20-triol 3727034 Click to see CC1CCC2C(C3CCC4C(C3CN2C1)CC5C4CC(C6C5(CCC(C6)O)C)O)(C)O 431.70 unknown via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acid amides
N,N'-bis(3-hydroxy-5-methylphenyl)oxamide 14355694 Click to see CC1=CC(=CC(=C1)O)NC(=O)C(=O)NC2=CC(=CC(=C2)C)O 300.31 unknown https://doi.org/10.1016/S0031-9422(00)97911-1
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / Alpha amino acids and derivatives / Alpha amino acids
4-Hydroxypipecolic acid 151907 Click to see C1CNC(CC1O)C(=O)O 145.16 unknown https://doi.org/10.1016/S0031-9422(00)97428-4
> 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
(2S,4R)-4-hydroxypiperidine-2-carboxylic acid 10898837 Click to see C1CNC(CC1O)C(=O)O 145.16 unknown https://doi.org/10.1016/S0031-9422(00)97428-4
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Glycosyl compounds / O-glycosyl compounds
4a-Hydroxy-4-(oxiran-2-yl)-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[3,4-c]pyran-8-one 14543432 Click to see C1COC(=O)C2=COC(C(C21O)C3CO3)OC4C(C(C(C(O4)CO)O)O)O 390.34 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Glycosyl compounds / Phenolic glycosides
(2S,3R,4R,5S,6R)-2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-9H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol 163190286 Click to see CC1=NC=CC2=C1NC3=C2C=CC(=C3OC4C(C(C(C(O4)CO)O)O)O)OC 390.40 unknown https://doi.org/10.1016/S0031-9422(00)94034-2
2-(hydroxymethyl)-6-[(7-methoxy-1-methyl-9H-pyrido[3,4-b]indol-8-yl)oxy]oxane-3,4,5-triol 21863061 Click to see CC1=NC=CC2=C1NC3=C2C=CC(=C3OC4C(C(C(C(O4)CO)O)O)O)OC 390.40 unknown https://doi.org/10.1016/S0031-9422(00)94034-2
2,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]benzoic acid 162989941 Click to see C1=CC(=C(C=C1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)OC3C(C(C(C(O3)CO)O)O)O 478.40 unknown https://doi.org/10.1016/0031-9422(75)85054-0
2,5-Bis[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]benzoic acid 162989940 Click to see C1=CC(=C(C=C1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)OC3C(C(C(C(O3)CO)O)O)O 478.40 unknown https://doi.org/10.1016/0031-9422(75)85054-0
Ruine 11972453 Click to see CC1=NC=CC2=C1NC3=C2C=CC(=C3OC4C(C(C(C(O4)CO)O)O)O)OC 390.40 unknown https://doi.org/10.1515/ZNC-1992-3-410
https://doi.org/10.1007/BF00563655
https://doi.org/10.1016/0031-9422(93)85453-X
> Organoheterocyclic compounds / Diazanaphthalenes / Benzodiazines / Quinazolines
(1S)-1-[(9R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl]-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one 162997745 Click to see C1CC2=NC3=CC=CC=C3C(N2C1)C4CCC5=NC6=CC=CC=C6C(=O)N45 356.40 unknown https://doi.org/10.1007/BF00563655
(3S)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol 667496 Click to see C1CN2CC3=CC=CC=C3N=C2C1O 188.23 unknown https://doi.org/10.1007/BF00563655
https://doi.org/10.1007/BF00564251
https://doi.org/10.1007/BF00567834
https://doi.org/10.1007/BF00565223
https://doi.org/10.1007/BF00563370
https://doi.org/10.1007/BF01373792
https://doi.org/10.1007/BF00569029
https://doi.org/10.1007/BF00571245
https://doi.org/10.1021/NP50018A025
(3S)-3-[(9R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl]-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one 21769549 Click to see C1CC2=NC3=CC=CC=C3C(N2C1)C4CCN5C4=NC6=CC=CC=C6C5=O 356.40 unknown https://doi.org/10.1007/BF00563655
(9R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-ol 906608 Click to see C1CC2=NC3=CC=CC=C3C(N2C1)O 188.23 unknown https://doi.org/10.1007/BF00567971
1-(1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl)-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one 162997744 Click to see C1CC2=NC3=CC=CC=C3C(N2C1)C4CCC5=NC6=CC=CC=C6C(=O)N45 356.40 unknown https://doi.org/10.1007/BF00563655
1-(1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-9-yl)propan-2-one 10955323 Click to see CC(=O)CC1C2=CC=CC=C2N=C3N1CCC3 228.29 unknown https://doi.org/10.1007/BF00563370
https://doi.org/10.1007/BF00563655
1-(3-Hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl)propan-2-one 14391707 Click to see CC(=O)CC1C2=CC=CC=C2N=C3N1CCC3O 244.29 unknown https://doi.org/10.1007/BF00563655
https://doi.org/10.1007/BF00568612
https://doi.org/10.1007/BF00565223
1-[(3S,9R)-3-hydroxy-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl]propan-2-one 154497166 Click to see CC(=O)CC1C2=CC=CC=C2N=C3N1CCC3O 244.29 unknown https://doi.org/10.1007/BF00568612
1-[(9R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-yl]propan-2-one 162932015 Click to see CC(=O)CC1C2=CC=CC=C2N=C3N1CCC3 228.29 unknown https://doi.org/10.1007/BF00563370
1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-9-ol 3756584 Click to see C1CC2=NC3=CC=CC=C3C(N2C1)O 188.23 unknown https://doi.org/10.1007/BF00563655
https://doi.org/10.1007/BF00567971
https://doi.org/10.1007/BF00565223
1H-Pyrrolo[2,1-b]quinazolin-9-one, 3-hydroxy-2,3-dihydro- 10242 Click to see C1CN2C(=NC3=CC=CC=C3C2=O)C1O 202.21 unknown https://doi.org/10.1007/S10600-009-9381-3
https://doi.org/10.1007/S10600-006-0086-6
2-(3-hydroxypropyl)-1H-quinazolin-4-one 6325786 Click to see C1=CC=C2C(=C1)C(=O)N=C(N2)CCCO 204.22 unknown https://doi.org/10.1007/BF00563655
https://doi.org/10.1007/BF00565223
https://doi.org/10.1007/BF00564251
CID 776133 776133 Click to see C1CN2C(=NC3=CC=CC=C3C2=O)C1O 202.21 unknown https://doi.org/10.1007/BF00564251
https://doi.org/10.1007/BF00567834
https://doi.org/10.1007/S10600-009-9381-3
https://doi.org/10.1007/BF00565223
https://doi.org/10.1007/S10600-006-0086-6
Deoxypeganine 442894 Click to see C1CC2=NC3=CC=CC=C3CN2C1 172.23 unknown https://doi.org/10.1007/BF00595109
Deoxyvasicinone 68261 Click to see C1CC2=NC3=CC=CC=C3C(=O)N2C1 186.21 unknown https://doi.org/10.1007/BF00563655
https://doi.org/10.1007/BF00564251
https://doi.org/10.1007/BF00567834
https://doi.org/10.1021/NP50018A025
Peganine 442929 Click to see C1CN2CC3=CC=CC=C3N=C2C1O 188.23 unknown https://doi.org/10.1007/BF00563655
https://doi.org/10.1007/BF00564251
https://doi.org/10.1007/BF00567834
https://doi.org/10.1007/S10600-009-9381-3
https://doi.org/10.1007/BF00565223
https://doi.org/10.1007/BF00563370
https://doi.org/10.1016/S0021-9673(01)93059-6
https://doi.org/10.1002/CBER.19360690903
https://doi.org/10.1007/BF00579504
https://doi.org/10.1007/BF01373792
https://doi.org/10.1007/S10600-006-0086-6
https://doi.org/10.1007/BF00569029
https://doi.org/10.1007/BF00571245
https://doi.org/10.1021/NP50018A025
Pyrrolo(2,1-b)quinazoline-3,7-diol, 1,2,3,9-tetrahydro-, (R)- 6452262 Click to see C1CN2CC3=C(C=CC(=C3)O)N=C2C1O 204.22 unknown via CMAUP database
Vasicine 72610 Click to see C1CN2CC3=CC=CC=C3N=C2C1O 188.23 unknown https://doi.org/10.1007/S10600-006-0086-6
https://doi.org/10.1007/S10600-009-9381-3
https://doi.org/10.1007/BF01373792
https://doi.org/10.1007/BF00579504
https://doi.org/10.1002/CBER.19360690903
Vasicinone 442935 Click to see C1CN2C(=NC3=CC=CC=C3C2=O)C1O 202.21 unknown https://doi.org/10.1007/BF00565223
https://doi.org/10.1007/BF00563655
https://doi.org/10.1007/BF00564251
https://doi.org/10.1007/BF00567834
> Organoheterocyclic compounds / Dihydrofurans / Furanones / Butenolides
Ascorbic Acid 54670067 Click to see C(C(C1C(=C(C(=O)O1)O)O)O)O 176.12 unknown https://doi.org/10.1007/978-3-662-04480-3_6
> Organoheterocyclic compounds / Indoles and derivatives / Pyridoindoles / Beta carbolines
10-methoxy-2-methyl-7,12-dihydro-6H-indolo[2,3-a]quinolizin-4-one 14558296 Click to see CC1=CC(=O)N2CCC3=C(C2=C1)NC4=C3C=CC(=C4)OC 280.32 unknown https://doi.org/10.3987/COM-89-4834
1H-Pyrido[3,4-b]indol-5-ol, 2,3,4,9-tetrahydro- 10375218 Click to see C1CNCC2=C1C3=C(N2)C=CC=C3O 188.23 unknown https://doi.org/10.1016/0031-9422(93)85453-X
5-Hydroxytryptoline 159959 Click to see C1CNCC2=C1C3=C(N2)C=CC(=C3)O 188.23 unknown https://doi.org/10.1016/0031-9422(93)85453-X
7-Methoxy-1,2,3,4-tetrahydropyrido[3,4-b]indole-9-carbaldehyde 14106930 Click to see COC1=CC2=C(C=C1)C3=C(N2C=O)CNCC3 230.26 unknown https://doi.org/10.3987/R-1987-06-1563
7-Methoxy-9-methyl-3,4-dihydropyrido[3,4-b]indole 118384447 Click to see CN1C2=C(C=CC(=C2)OC)C3=C1C=NCC3 214.26 unknown https://doi.org/10.1016/S0031-9422(00)86329-3
7-Methoxy-9H-pyrido[3,4-b]indole 9815570 Click to see COC1=CC2=C(C=C1)C3=C(N2)C=NC=C3 198.22 unknown https://doi.org/10.3987/COM-89-4834
Harmalacidine 179484 Click to see COC1=CC2=C(C=C1)C3=C(N2)C(=O)NCC3 216.24 unknown https://doi.org/10.3987/R-1987-06-1563
Harmalidine 13819666 Click to see CC1(CN2C3=C(C=CC(=C3)OC)C4=C2C1=NCC4)C 254.33 unknown https://doi.org/10.1016/S0031-9422(00)81861-0
Ojvcxvgfrrzmrp-uhfffaoysa- 14191996 Click to see COC1=CC2=C(C=C1)C3=C(N2)C4=CC=CC(=O)N4CC3 266.29 unknown https://doi.org/10.3987/COM-88-4490
https://doi.org/10.3987/R-1987-06-1563
> Organoheterocyclic compounds / Indoles and derivatives / Tryptamines and derivatives
6-Hydroxytryptamine 160463 Click to see C1=CC2=C(C=C1O)NC=C2CCN 176.21 unknown https://doi.org/10.1007/BF00563655
https://doi.org/10.1016/0031-9422(75)85054-0
> Organoheterocyclic compounds / Indoles and derivatives / Tryptamines and derivatives / Serotonins
Serotonin 5202 Click to see C1=CC2=C(C=C1O)C(=CN2)CCN 176.21 unknown https://doi.org/10.1007/BF00563655
https://doi.org/10.1515/ZNC-1992-3-410
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC426218/
https://doi.org/10.1016/0031-9422(93)85453-X
https://doi.org/10.1016/0031-9422(75)85054-0
> Organoheterocyclic compounds / Piperidines
1-(3-Hydroxy-1,2,3,4,4a,8a-hexahydroisoquinolin-1-yl)propan-2-one 163035232 Click to see CC(=O)CC1C2C=CC=CC2CC(N1)O 207.27 unknown https://doi.org/10.1007/BF00563655
1-[(1R,3S,4aR,8aS)-3-hydroxy-1,2,3,4,4a,8a-hexahydroisoquinolin-1-yl]propan-2-one 163035233 Click to see CC(=O)CC1C2C=CC=CC2CC(N1)O 207.27 unknown https://doi.org/10.1007/BF00563655
> Organoheterocyclic compounds / Pyrrolidines / Phenylpyrrolidines
Benzenamine, N,N-dimethyl-2-(1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-yl)- 626005 Click to see CN(C)C1=CC=CC=C1C2CCN3C2=NC4=CC=CC=C4C3 291.40 unknown via CMAUP database
> Organoheterocyclic compounds / Quinolines and derivatives
2-Methylquinoline 7060 Click to see CC1=NC2=CC=CC=C2C=C1 143.18 unknown https://doi.org/10.1007/BF00563655
Quinoline 7047 Click to see C1=CC=C2C(=C1)C=CC=N2 129.16 unknown https://doi.org/10.1007/BF00563655
> Organoheterocyclic compounds / Quinolines and derivatives / Pyrroloquinolines
1,2,3,4-Tetrahydro-9h-pyrrolo[3,4-b]quinolin-9-one 12884011 Click to see C1C2=C(CN1)NC3=CC=CC=C3C2=O 186.21 unknown https://doi.org/10.1016/S0031-9422(00)86329-3
> Phenylpropanoids and polyketides / Flavonoids / Flavones / Flavonols
Kaempferol 5280863 Click to see C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O 286.24 unknown https://doi.org/10.1021/NP50032A022
Quercetin 5280343 Click to see C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O 302.23 unknown https://doi.org/10.1021/NP50032A022
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid C-glycosides / Flavonoid 8-C-glycosides
8-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one 102064906 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)CO)O)O)CO)O)O)O)O)O 754.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
8-[(2S,3R,4S,5S,6S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one 162998076 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)CO)O)O)CO)O)O)O)O)O 754.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
8-[3-[4,5-Dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one 74977544 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)CO)O)O)CO)O)O)O)O)O 754.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
Cytisoside 44257872 Click to see COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O 446.40 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
> Phenylpropanoids and polyketides / Flavonoids / Flavonoid glycosides / Flavonoid O-glycosides / Flavonoid-7-O-glycosides
[(2S,3R,4R,5S,6S)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate 102064904 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)OC(=O)C)O 796.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
[(2S,3S,4R,5S,6S)-2-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-2-[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate 162899284 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)OC(=O)C)O 796.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
[2-[4,5-Dihydroxy-2-[5-hydroxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate 74977553 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)OC(=O)C)O 796.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
5-hydroxy-2-(4-methoxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one 102442676 Click to see CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=CC3=O)C4=CC=C(C=C4)OC)O)O)O)O 430.40 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
5-hydroxy-2-(4-methoxyphenyl)-7-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one 162906360 Click to see CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=CC3=O)C4=CC=C(C=C4)OC)O)O)O)O 430.40 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one 102064905 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)OC)O)CO)O)O)CO)O)O)O)O)O 754.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one 162850281 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)OC)O)CO)O)O)CO)O)O)O)O)O 754.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
7-[3-[4,5-Dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one 74977554 Click to see CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)OC)O)CO)O)O)CO)O)O)O)O)O 754.70 unknown https://doi.org/10.1016/S0031-9422(96)00531-6
Peganetin 5491743 Click to see CC1C(C(C(C(O1)OC2C(OC(C(C2O)OC3C(C(C(C(O3)COC(=O)C)O)O)O)OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)OC)O)COC7C(C(C(C(O7)CO)O)O)O)O)O)O 958.90 unknown https://doi.org/10.1021/NP50050A028
> Phenylpropanoids and polyketides / Isoflavonoids / Isoflavonoid O-glycosides
7-[(2S,3R,4S,6S)-3,4-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-3-(4-methoxyphenyl)chromen-4-one 6325060 Click to see CC1C(C(C(C(O1)OCC2CC(C(C(O2)OC3=CC4=C(C=C3)C(=O)C(=CO4)C5=CC=C(C=C5)OC)O)O)O)O)O 560.50 unknown via CMAUP database

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