Orthosiphol U

CNP0226794.1 · C33H42O11 · View on COCONUT ↗

2D Structure

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Identifiers

Name	Orthosiphol U
IUPAC Name	[(2~{S},3~{S},4~{R},4~{a}~{S},4~{b}~{S},5~{R},7~{R},8~{a}~{R},9~{R},10~{a}~{S})-2,3,9-triacetoxy-5,8~{a}-dihydroxy-1,1,4~{a},7-tetramethyl-8-oxo-7-vinyl-3,4,4~{b},5,6,9,10,10~{a}-octahydro-2~{H}-phenanthren-4-yl] benzoate
COCONUT ID	CNP0226794.1
InChIKey	VXLLVGCAWRWNCI-FQNFDSBVSA-N
InChI	InChI=1S/C33H42O11/c1-9-31(7)16-21(37)25-32(8)22(15-23(41-17(2)34)33(25,40)29(31)39)30(5,6)26(43-19(4)36)24(42-18(3)35)27(32)44-28(38)20-13-11-10-12-14-20/h9-14,21-27,37,40H,1,15-16H2,2-8H3/t21-,22+,23-,24+,25-,26-,27+,31+,32+,33+/m1/s1
SMILES	C=C[C@@]1(C)C[C@@H](O)[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](OC(C)=O)[C@H](OC(=O)C3=CC=CC=C3)[C@@]12C

Properties

Molecular Formula	C33H42O11
Molecular Weight	614.69
Exact Mass	614.27271
Log P (ALogP)	2.95
TPSA	162.73
H-Bond Donors / Acceptors	2 / 11
Rotatable Bonds	6
Lipinski's Rule of 5 Violations	2
QED Drug-likeness	0.28
NP-likeness	2.53

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 (3)

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