orthosiphol B

CNP0294947.1 · C38H44O11 · View on COCONUT ↗

2D Structure

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Identifiers

Name	orthosiphol B
IUPAC Name	[(2~{R},4~{R},4~{a}~{S},4~{b}~{S},5~{R},6~{S},7~{S},8~{a}~{S},10~{R},10~{a}~{R})-7,10-diacetoxy-5-benzoyloxy-6,10~{a}-dihydroxy-2,4~{b},8,8-tetramethyl-1-oxo-2-vinyl-4,4~{a},5,6,7,8~{a},9,10-octahydro-3~{H}-phenanthren-4-yl] benzoate
COCONUT ID	CNP0294947.1
CAS	144078-08-0
InChIKey	BXKNTIMTKVZYDP-OFUWLHILSA-N
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
SMILES	C=C[C@@]1(C)C[C@@H](OC(=O)C2=CC=CC=C2)[C@H]2[C@](O)(C1=O)[C@H](OC(C)=O)C[C@H]1C(C)(C)[C@H](OC(C)=O)[C@H](O)[C@H](OC(=O)C3=CC=CC=C3)[C@@]12C

Properties

Molecular Formula	C38H44O11
Molecular Weight	676.76
Exact Mass	676.28836
Log P (ALogP)	4.24
TPSA	162.73
H-Bond Donors / Acceptors	2 / 11
Rotatable Bonds	7
Lipinski's Rule of 5 Violations	2
QED Drug-likeness	0.25
NP-likeness	2.19

Classification

NP Pathway	Terpenoids
NP Superclass	Diterpenoids
NP Class	Pimarane and Isopimarane diterpenoids
Chemical Superclass	Lipids and lipid-like molecules
Chemical Class	Prenol lipids
Chemical Subclass	Diterpenoids

Reported in GR-MAPs Plants

Oryza sativa	as “Oryza sativa” in COCONUT

References (10)

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.

COCONUT Compound