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COCONUT Compound

7-O-deacetylorthosiphol O

CNP0166758.1 · C36H42O10 · View on COCONUT ↗

2D Structure

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Identifiers

Name7-O-deacetylorthosiphol O
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})-3-acetoxy-4-benzoyloxy-5,8~{a},9-trihydroxy-1,1,4~{a},7-tetramethyl-8-oxo-7-vinyl-3,4,4~{b},5,6,9,10,10~{a}-octahydro-2~{H}-phenanthren-2-yl] benzoate
COCONUT IDCNP0166758.1
InChIKeyADVJBOBFOAHJLA-KXWDHPLKSA-N
InChIInChI=1S/C36H42O10/c1-7-34(5)19-23(38)27-35(6)24(18-25(39)36(27,43)32(34)42)33(3,4)28(45-30(40)21-14-10-8-11-15-21)26(44-20(2)37)29(35)46-31(41)22-16-12-9-13-17-22/h7-17,23-29,38-39,43H,1,18-19H2,2-6H3/t23-,24+,25-,26+,27-,28-,29+,34+,35+,36+/m1/s1
SMILESC=C[C@@]1(C)C[C@@H](O)[C@H]2[C@](O)(C1=O)[C@H](O)C[C@H]1C(C)(C)[C@H](OC(=O)C3=CC=CC=C3)[C@H](OC(C)=O)[C@H](OC(=O)C3=CC=CC=C3)[C@@]12C

Properties

Molecular FormulaC36H42O10
Molecular Weight634.72
Exact Mass634.27780
Log P (ALogP)3.67
TPSA156.66
H-Bond Donors / Acceptors3 / 10
Rotatable Bonds6
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.24
NP-likeness2.26

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. 10.1016/j.bmcl.2019.126841
  2. 10.1021/NP020455X
  3. 10.1021/np020455x
  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.