Summary

IMPPAT Phytochemical identifier: IMPHY011447

Phytochemical name: [(1R,2R,6S,7S,8R,10S,11S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl

Synonymous chemical names:
daphnane, mezerein

External chemical identifiers:
CID:5281382, ChEMBL:CHEMBL126750, ChEBI:6918

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Chemical structure information

SMILES:
OC[C@]12O[C@H]1[C@H]1[C@H]3OC4(O[C@]1([C@H]1[C@@]([C@@H]2O)(O)C(=O)C(=C1)C)[C@@H]([C@H]([C@@]3(O4)C(=C)C)OC(=O)/C=C/C=C/c1ccccc1)C)c1ccccc1

InChI:
InChI=1S/C38H38O10/c1-21(2)36-30(44-27(40)18-12-11-15-24-13-7-5-8-14-24)23(4)37-26-19-22(3)29(41)35(26,43)33(42)34(20-39)31(45-34)28(37)32(36)46-38(47-36,48-37)25-16-9-6-10-17-25/h5-19,23,26,28,30-33,39,42-43H,1,20H2,2-4H3/b15-11+,18-12+/t23-,26-,28+,30-,31+,32-,33-,34+,35-,36+,37+,38?/m1/s1

InChIKey:
DLEDLHFNQDHEOJ-HBJWEEFJSA-N

DeepSMILES:
OC[C@]O[C@H]3[C@H][C@H]OCO[C@]6[C@H][C@@][C@@H]%12O))O)C=O)C=C5)C)))))[C@@H][C@H][C@@]8O7)C=C)C)))OC=O)/C=C/C=C/cccccc6)))))))))))))C))))cccccc6

Functional groups:
C=C(C)C, CC1=CCCC1=O, CO, C[C@]1(C)O[C@H]1C, c/C=C/C=C/C(=O)OC, cC1(OC)OCCO1

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(C=CC=Cc1ccccc1)OC1CC23OC4(c5ccccc5)OC1C(O4)C2C1OC1CC1C(=O)C=CC13

Scaffold Graph/Node level:
OC(CCCCC1CCCCC1)OC1CC23OC4(C5CCCCC5)OC1C(O4)C2C1OC1CC1C(O)CCC13

Scaffold Graph level:
CC(CCCCC1CCCCC1)CC1CC23CC4(C5CCCCC5)CC1C(C4)C2C1CC1CC1C(C)CCC13

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Prenol lipids

ClassyFire Subclass: Diterpenoids

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Diterpenoids

NP Classifier Class: Daphnane diterpenoids

NP-Likeness score: 3.013

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Chemical structure download