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Trifolirhizin

PubChem CID: 442827

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Compound Synonyms Trifolirhizin, 6807-83-6, trifolrhizin, MFCD00238700, (-)-maackiain-3-O-glucoside, CHEBI:9714, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-3,4,5-triol, DTXSID70987516, (-)-Maackiain 3-O-glucoside, Sophojaponicin B2, (2S,3R,4S,5S,6R)-2-(((6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4',5':5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, CHEMBL454878, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(((1R,12R)-5,7,11,19-tetraoxapentacyclo(10.8.0.02,10.04,8.013,18)icosa-2,4(8),9,13(18),14,16-hexaen-16-yl)oxy)oxane-3,4,5-triol, Trifolirhizin (Standard), ACon1_002295, HY-N0616R, VGSYCWGXBYZLLE-QEEQPWONSA-N, DTXCID501414675, HY-N0616, s9425, AKOS030632879, CCG-269193, FT65534, NCGC00169980-01, NCGC00169980-03, Trifolirhizin, >=95% (LC/MS-ELSD), beta-D-Glucopyranoside, 6a,12a-dihydro-6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-yl, (6aR-cis)-, DA-68330, CS-0009612, BRD-K43094903-001-01-3, Q27108480
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 136.0
Hydrogen Bond Donor Count 4.0
Pfizer 3 75 Rule True
Scaffold Graph Level C1CCC(CC2CCC3C(CCC4C5CC6CCCC6CC5CC34)C2)CC1
Np Classifier Class Pterocarpan
Deep Smiles OC[C@H]O[C@@H]Occcccc6)OC[C@@H][C@H]6Occ5cccc6)OCO5)))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Heavy Atom Count 32.0
Classyfire Class Isoflavonoids
Description (-)-maackiain-3-o-glucoside, also known as trifolrhizin, is a member of the class of compounds known as pterocarpans. Pterocarpans are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids (-)-maackiain-3-o-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (-)-maackiain-3-o-glucoside can be found in a number of food items such as pepper (c. pubescens), loquat, nopal, and kiwi, which makes (-)-maackiain-3-o-glucoside a potential biomarker for the consumption of these food products.
Scaffold Graph Node Level C1CCC(OC2CCC3C(C2)OCC2C4CC5OCOC5CC4OC32)OC1
Classyfire Subclass Furanoisoflavonoids
Isotope Atom Count 0.0
Molecular Complexity 679.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 7.0
Iupac Name (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-3,4,5-triol
Prediction Hob 0.0
Class Isoflavonoids
Veber Rule True
Classyfire Superclass Phenylpropanoids and polyketides
Xlogp 0.6
Superclass Phenylpropanoids and polyketides
Subclass Furanoisoflavonoids
Gsk 4 400 Rule False
Molecular Formula C22H22O10
Scaffold Graph Node Bond Level c1cc2c(cc1OC1CCCCO1)OCC1c3cc4c(cc3OC21)OCO4
Prediction Swissadme 0.0
Inchi Key VGSYCWGXBYZLLE-QEEQPWONSA-N
Silicos It Class Soluble
Fcsp3 0.4545454545454545
Logs -4.405
Rotatable Bond Count 3.0
Logd 1.258
Synonyms (-)-Maackiain 3-O-glucoside, (-)-maackiain-3-o-glucoside, trifolirhizin
Esol Class Soluble
Functional Groups CO, c1cOCO1, cOC, cO[C@@H](C)OC
Compound Name Trifolirhizin
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 446.121
Formal Charge 0.0
Monoisotopic Mass 446.121
Hydrogen Bond Acceptor Count 10.0
Molecular Weight 446.4
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 7.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Lipinski Rule Of 5 True
Esol -3.1975296000000006
Inchi InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1
Smiles C1[C@@H]2[C@H](C3=C(O1)C=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC5=CC6=C(C=C25)OCO6
Nring 6.0
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 0.0
Egan Rule False
Taxonomy Direct Parent Pterocarpans
Np Classifier Superclass Isoflavonoids

  • 1. Outgoing r'ship FOUND_IN to/from Abelia Chinensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Asimina Parviflora (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 3. Outgoing r'ship FOUND_IN to/from Atraphaxis Spinosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 4. Outgoing r'ship FOUND_IN to/from Baccharis Neglecta (Plant) Rel Props:Source_db:npass_chem_all
  • 5. Outgoing r'ship FOUND_IN to/from Centaurea Maculosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 6. Outgoing r'ship FOUND_IN to/from Chondrodendron Tomentosum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 7. Outgoing r'ship FOUND_IN to/from Clerodendrum Bungei (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Cordia Leucocephala (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 9. Outgoing r'ship FOUND_IN to/from Diospyros Assimilis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Embelia Parviflora (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Embelia Schimperi (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 12. Outgoing r'ship FOUND_IN to/from Ephedra Sinica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 13. Outgoing r'ship FOUND_IN to/from Epilobium Hirsutum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 14. Outgoing r'ship FOUND_IN to/from Eria Anomala (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 15. Outgoing r'ship FOUND_IN to/from Erysimum Leptophyllum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 16. Outgoing r'ship FOUND_IN to/from Erythrina Melanacantha (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 17. Outgoing r'ship FOUND_IN to/from Esenbeckia Leiocarpa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 18. Outgoing r'ship FOUND_IN to/from Euphorbia Nematocypha (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 19. Outgoing r'ship FOUND_IN to/from Faramea Salicifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 20. Outgoing r'ship FOUND_IN to/from Gymnocalycium Schickendantzii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 21. Outgoing r'ship FOUND_IN to/from Haplophyllum Obtusifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 22. Outgoing r'ship FOUND_IN to/from Helichrysum Tenuifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 23. Outgoing r'ship FOUND_IN to/from Hypericum Styphelioides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 24. Outgoing r'ship FOUND_IN to/from Lemaireocereus Longispinus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 25. Outgoing r'ship FOUND_IN to/from Lythrum Salicaria (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 26. Outgoing r'ship FOUND_IN to/from Monsonia Senegalensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 27. Outgoing r'ship FOUND_IN to/from Morella Rubra (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 28. Outgoing r'ship FOUND_IN to/from Onopordum Acanthium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 29. Outgoing r'ship FOUND_IN to/from Pancratium Sickenbergeri (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 30. Outgoing r'ship FOUND_IN to/from Picrasma Quassioides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 31. Outgoing r'ship FOUND_IN to/from Piper Regnellii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 32. Outgoing r'ship FOUND_IN to/from Plathymenia Reticulata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 33. Outgoing r'ship FOUND_IN to/from Pteridium Esculentum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 34. Outgoing r'ship FOUND_IN to/from Simarouba Glauca (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 35. Outgoing r'ship FOUND_IN to/from Sophora Alopecuroides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 36. Outgoing r'ship FOUND_IN to/from Sophora Flavescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 37. Outgoing r'ship FOUND_IN to/from Sophora Tonkinensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 38. Outgoing r'ship FOUND_IN to/from Syzygium Polycephaloides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 39. Outgoing r'ship FOUND_IN to/from Trifolium Pratense (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279
  • 40. Outgoing r'ship FOUND_IN to/from Vellozia Nanuzae (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 41. Outgoing r'ship FOUND_IN to/from Vernonia Fagifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
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