Summary

IMPPAT Phytochemical identifier: IMPHY002852

Phytochemical name: (3S,4S)-4-[(Z)-1-carboxy-3-[[(1R,19R,21S,22R,23R)-6,7,8,11,12,13,22-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyl)oxy-2,17,20-trioxatetracyclo[17.3.1.04,9.010,15]tricosa-4,6,8,10,12,14-hexaen-23

Synonymous chemical names:
repandusinic acid a

External chemical identifiers:
CID:14483070

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Chemical structure information

SMILES:
OC(=O)/C=C(/[C@H]1[C@H](OC(=O)c2c1c(O)c(c(c2)O)O)C(=O)O)C(=O)O[C@@H]1[C@H]2COC(=O)c3cc(O)c(c(c3-c3c(C(=O)O[C@@H]1[C@H]([C@@H](O2)OC(=O)c1cc(O)c(c(c1)O)O)O)cc(O)c(c3O)O)O)O

InChI:
InChI=1S/C41H30O28/c42-13-1-8(2-14(43)24(13)49)36(59)69-41-31(56)34-32(66-40(63)12(6-19(47)48)23-22-11(5-17(46)27(52)30(22)55)38(61)67-33(23)35(57)58)18(65-41)7-64-37(60)9-3-15(44)25(50)28(53)20(9)21-10(39(62)68-34)4-16(45)26(51)29(21)54/h1-6,18,23,31-34,41-46,49-56H,7H2,(H,47,48)(H,57,58)/b12-6-/t18-,23-,31-,32-,33+,34-,41+/m1/s1

InChIKey:
WUTXIOAKRFKQHK-IOVBSTNJSA-N

DeepSMILES:
OC=O)/C=C/[C@H][C@H]OC=O)cc6cO)ccc6)O))O)))))))C=O)O))))C=O)O[C@@H][C@H]COC=O)cccO)ccc6-ccC=O)O[C@@H]%16[C@H][C@@H]O%18)OC=O)cccO)ccc6)O))O))))))))O)))))ccO)cc6O))O)))))))O))O

Functional groups:
C/C(=C/C(=O)O)C(=O)OC, CC(=O)O, CO, cC(=O)OC, cC(=O)O[C@@H](C)OC, cO

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
C=C(C(=O)OC1C2CC(OC(=O)c3ccccc3)OC1COC(=O)c1ccccc1-c1ccccc1C(=O)O2)C1COC(=O)c2ccccc21

Scaffold Graph/Node level:
CC(C(O)OC1C2COC(O)C3CCCCC3C3CCCCC3C(O)OC1CC(OC(O)C1CCCCC1)O2)C1COC(O)C2CCCCC21

Scaffold Graph level:
CC(CC1CC2CCC(C)C3CCCCC3C3CCCCC3C(C)CC(C1)C2CC(C)C(C)C1CCC(C)C2CCCCC21)C1CCCCC1

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Phenylpropanoids and polyketides

ClassyFire Class: Tannins

ClassyFire Subclass: Hydrolyzable tannins

NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids

NP Classifier Superclass: Phenolic acids (C6-C1)

NP Classifier Class: Gallotannins

NP-Likeness score: 1.464

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Chemical structure download