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COCONUT Compound

orthosiphol D

CNP0338142.2 · C31H36O9 · View on COCONUT ↗

2D Structure

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Identifiers

Nameorthosiphol D
IUPAC Name[(2~{R},4~{R},4~{a}~{S},4~{b}~{R},8~{a}~{R},10~{R},10~{a}~{R})-6,10-diacetoxy-10~{a}-hydroxy-2,4~{b},8,8-tetramethyl-1,7-dioxo-2-vinyl-3,4,4~{a},8~{a},9,10-hexahydrophenanthren-4-yl] benzoate
COCONUT IDCNP0338142.2
InChIKeyLSZJDNYREMWISO-FHGPSSOVSA-N
InChIInChI=1S/C31H36O9/c1-8-29(6)15-20(40-26(35)19-12-10-9-11-13-19)24-30(7)16-21(38-17(2)32)25(34)28(4,5)22(30)14-23(39-18(3)33)31(24,37)27(29)36/h8-13,16,20,22-24,37H,1,14-15H2,2-7H3/t20-,22+,23-,24-,29+,30+,31+/m1/s1
SMILESC=C[C@@]1(C)C[C@@H](OC(=O)C2=CC=CC=C2)[C@@H]2[C@@]3(C)C=C(OC(C)=O)C(=O)C(C)(C)[C@@H]3C[C@@H](OC(C)=O)[C@@]2(O)C1=O

Properties

Molecular FormulaC31H36O9
Molecular Weight552.62
Exact Mass552.23593
Log P (ALogP)3.74
TPSA133.27
H-Bond Donors / Acceptors1 / 9
Rotatable Bonds5
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.33
NP-likeness2.44

Classification

NP PathwayTerpenoids
NP SuperclassDiterpenoids
NP ClassNorpimarane and Norisopimarane 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 (6)

  1. 10.1016/0031-9422(93)85530-5
  2. 10.1021/NP020455X
  3. 10.1021/NP030471+
  4. 10.1021/np020455x
  5. 10.1055/S-2002-23137
  6. 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.