Summary

IMPPAT Phytochemical identifier: IMPHY011295

Phytochemical name: (3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren

Synonymous chemical names:
tholloside

External chemical identifiers:
CID:23312

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Chemical structure information

SMILES:
O=C[C@@]12CC[C@@H](C[C@@]2(O)CCC2C1C(O)C[C@]1([C@]2(O)CC[C@@H]1C1=CC(=O)OC1)C)O[C@H]1OC(C)[C@H](C(C1O)O)O

InChI:
InChI=1S/C29H42O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)21-18(4-7-28(27,36)10-16)29(37)8-5-17(15-9-20(32)38-12-15)26(29,2)11-19(21)31/h9,13-14,16-19,21-25,31,33-37H,3-8,10-12H2,1-2H3/t14?,16-,17+,18?,19?,21?,22+,23?,24?,25+,26+,27-,28-,29-/m0/s1

InChIKey:
AZOXLPPOBHVORY-RQTNDROZSA-N

DeepSMILES:
O=C[C@]CC[C@@H]C[C@@]6O)CCCC%10CO)C[C@][C@]6O)CC[C@@H]5C=CC=O)OC5)))))))))C))))))))))O[C@H]OCC)[C@H]CC6O))O))O

Functional groups:
CC1=CC(=O)OC1, CC=O, CO, CO[C@@H](C)OC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1C=C(C2CCC3C2CCC2C4CCC(OC5CCCCO5)CC4CCC23)CO1

Scaffold Graph/Node level:
OC1CC(C2CCC3C2CCC2C4CCC(OC5CCCCO5)CC4CCC23)CO1

Scaffold Graph level:
CC1CCC(C2CCC3C2CCC2C4CCC(CC5CCCCC5)CC4CCC23)C1

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Steroids and steroid derivatives

ClassyFire Subclass: Steroid lactones

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Steroids

NP Classifier Class: Cardenolides

NP-Likeness score: 3.238

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Chemical structure download