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COCONUT Compound

orthosiphol A

CNP0210323.1 · C38H44O11 · View on COCONUT ↗

2D Structure

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Identifiers

Nameorthosiphol A
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})-6,10-diacetoxy-5-benzoyloxy-7,10~{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 IDCNP0210323.1
CAS142741-25-1
InChIKeyHIBFBUSEUDRQMX-OFUWLHILSA-N
InChIInChI=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(41)28(47-22(3)40)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
SMILESC=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](O)[C@H](OC(C)=O)[C@H](OC(=O)C3=CC=CC=C3)[C@@]12C

Properties

Molecular FormulaC38H44O11
Molecular Weight676.76
Exact Mass676.28836
Log P (ALogP)4.24
TPSA162.73
H-Bond Donors / Acceptors2 / 11
Rotatable Bonds7
Lipinski's Rule of 5 Violations2
QED Drug-likeness0.25
NP-likeness2.24

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 (11)

  1. 10.1016/0031-9422(93)85530-5
  2. 10.1016/S0040-4020(01)89868-9
  3. 10.1016/S0040-4039(00)91583-1
  4. 10.1021/NP000607T
  5. 10.1021/NP020455X
  6. 10.1021/np000607t
  7. 10.1021/np020455x
  8. 10.1248/BPB.26.468
  9. 10.1248/CPB.47.695
  10. 10.1248/CPB.47.911
  11. 10.1248/CPB.48.433

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.