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COCONUT Compound

Orthosiphol M

CNP0312344.1 · C31H38O10 · View on COCONUT ↗

2D Structure

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Identifiers

NameOrthosiphol M
IUPAC Name[(2~{S},3~{S},4~{R},4~{a}~{S},4~{b}~{R},7~{R},8~{a}~{R},9~{R},10~{a}~{S})-3,9-diacetoxy-2,8~{a}-dihydroxy-1,1,4~{a},7-tetramethyl-5,8-dioxo-7-vinyl-2,3,4,4~{b},6,9,10,10~{a}-octahydrophenanthren-4-yl] benzoate
COCONUT IDCNP0312344.1
InChIKeyGTEFXIUCQAABAV-FYEHOKTBSA-N
InChIInChI=1S/C31H38O10/c1-8-29(6)15-19(34)23-30(7)20(14-21(39-16(2)32)31(23,38)27(29)37)28(4,5)24(35)22(40-17(3)33)25(30)41-26(36)18-12-10-9-11-13-18/h8-13,20-25,35,38H,1,14-15H2,2-7H3/t20-,21+,22-,23+,24+,25-,29-,30-,31-/m0/s1
SMILESC=C[C@@]1(C)CC(=O)[C@H]2[C@](O)(C1=O)[C@H](OC(C)=O)C[C@H]1C(C)(C)[C@H](O)[C@H](OC(C)=O)[C@H](OC(=O)C3=CC=CC=C3)[C@@]12C

Properties

Molecular FormulaC31H38O10
Molecular Weight570.64
Exact Mass570.24650
Log P (ALogP)2.58
TPSA153.50
H-Bond Donors / Acceptors2 / 10
Rotatable Bonds5
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.31
NP-likeness2.58

Classification

NP PathwayTerpenoids
NP SuperclassDiterpenoids
NP ClassPimarane and Isopimarane diterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassDiterpenoids

Reported in GR-MAPs Plants

Oryza sativa as “Oryza sativa” in COCONUT

References (4)

  1. 10.1002/CHIN.200334172
  2. 10.1021/NP000607T
  3. 10.1021/np000607t
  4. 10.1248/BPB.26.468

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.