Summary

IMPPAT Phytochemical identifier: IMPHY002486

Phytochemical name: 3-[2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-2-oxoethyl]-2H-furan-5-one

Synonymous chemical names:
14-deoxy-11-oxo-andrographolide, 14-deoxy-11-oxoandrographolide, homoandrographolide

External chemical identifiers:
CID:101593061, ZINC:ZINC000238761695

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Chemical structure information

SMILES:
OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C(=O)CC1=CC(=O)OC1)C

InChI:
InChI=1S/C20H28O5/c1-12-4-5-15-19(2,7-6-16(23)20(15,3)11-21)18(12)14(22)8-13-9-17(24)25-10-13/h9,15-16,18,21,23H,1,4-8,10-11H2,2-3H3/t15-,16+,18-,19+,20-/m0/s1

InChIKey:
XBINLYXLOLWNSB-ZRSLWSEBSA-N

DeepSMILES:
OC[C@]C)[C@H]O)CC[C@@][C@@H]6CCC=C)[C@H]6C=O)CC=CC=O)OC5))))))))))))C

Functional groups:
C=C(C)C, CC(C)=O, CC1=CC(=O)OC1, CO

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
C=C1CCC2CCCCC2C1C(=O)CC1=CC(=O)OC1

Scaffold Graph/Node level:
CC1CCC2CCCCC2C1C(O)CC1COC(O)C1

Scaffold Graph level:
CC1CCC(CC(C)C2C(C)CCC3CCCCC32)C1

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Prenol lipids

ClassyFire Subclass: Terpene lactones

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Diterpenoids

NP Classifier Class: Labdane diterpenoids

NP-Likeness score: 2.843

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Chemical structure download