Summary

IMPPAT Phytochemical identifier: IMPHY009273

Phytochemical name: orthosiphol B

Synonymous chemical names:
orthosiphol b

External chemical identifiers:
CID:15385859, ChEMBL:CHEMBL509129, ZINC:ZINC000049899625, SureChEMBL:SCHEMBL1996101

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Chemical structure information

SMILES:
C=C[C@@]1(C)C[C@@H](OC(=O)c2ccccc2)[C@H]2[C@@](C1=O)(O)[C@H](OC(=O)C)C[C@@H]1[C@]2(C)[C@@H](OC(=O)c2ccccc2)[C@@H](O)[C@H](C1(C)C)OC(=O)C

InChI:
InChI=1S/C38H44O11/c1-8-36(6)20-25(48-32(42)23-15-11-9-12-16-23)29-37(7)26(19-27(46-21(2)39)38(29,45)34(36)44)35(4,5)30(47-22(3)40)28(41)31(37)49-33(43)24-17-13-10-14-18-24/h8-18,25-31,41,45H,1,19-20H2,2-7H3/t25-,26+,27-,28+,29-,30-,31+,36+,37+,38+/m1/s1

InChIKey:
BXKNTIMTKVZYDP-OFUWLHILSA-N

DeepSMILES:
C=C[C@@]C)C[C@@H]OC=O)cccccc6))))))))[C@H][C@@]C6=O))O)[C@H]OC=O)C)))C[C@@H][C@]6C)[C@@H]OC=O)cccccc6))))))))[C@@H]O)[C@H]C6C)C))OC=O)C

Functional groups:
C=CC, CC(=O)OC, CC(C)=O, CO, cC(=O)OC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(OC1CCCC2CCC3C(=O)CCC(OC(=O)c4ccccc4)C3C21)c1ccccc1

Scaffold Graph/Node level:
OC1CCC(OC(O)C2CCCCC2)C2C1CCC1CCCC(OC(O)C3CCCCC3)C12

Scaffold Graph level:
CC(CC1CCCC2CCC3C(C)CCC(CC(C)C4CCCCC4)C3C21)C1CCCCC1

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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: Pimarane and Isopimarane diterpenoids

NP-Likeness score: 2.19

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Chemical structure download