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COCONUT Compound

Penupogenin

CNP0281161.2 · C30H40O7 · View on COCONUT ↗

2D Structure

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Identifiers

NamePenupogenin
IUPAC Name[(3~{S},8~{S},9~{R},10~{R},12~{R},13~{R},14~{R},17~{S})-3,8,14,17-tetrahydroxy-17-[(1~{R})-1-hydroxyethyl]-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (~{E})-3-phenylprop-2-enoate
COCONUT IDCNP0281161.2
CAS27526-87-0
InChIKeyCSSZPOBBUXFMAA-JWBRRKRUSA-N
InChIInChI=1S/C30H40O7/c1-19(31)28(34)15-16-30(36)27(28,3)24(37-25(33)10-9-20-7-5-4-6-8-20)18-23-26(2)13-12-22(32)17-21(26)11-14-29(23,30)35/h4-11,19,22-24,31-32,34-36H,12-18H2,1-3H3/b10-9+/t19-,22+,23-,24-,26+,27-,28-,29+,30-/m1/s1
SMILESC[C@@H](O)[C@]1(O)CC[C@@]2(O)[C@]1(C)[C@H](OC(=O)/C=C/C1=CC=CC=C1)C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@]12O

Properties

Molecular FormulaC30H40O7
Molecular Weight512.64
Exact Mass512.27740
Log P (ALogP)2.89
TPSA127.45
H-Bond Donors / Acceptors5 / 7
Rotatable Bonds4
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.24
NP-likeness2.80

Classification

NP PathwayTerpenoids
NP SuperclassSteroids
NP ClassPregnane steroids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassSteroids and steroid derivatives
Chemical SubclassPregnane steroids

Reported in GR-MAPs Plants

Gymnema sylvester as “Gymnema sylvestre” in COCONUT

References (6)

  1. 10.1002/JCCS.199900114
  2. 10.1016/0031-9422(91)80034-X
  3. 10.1016/J.STEROIDS.2007.09.004
  4. 10.1021/NP50119A004
  5. 10.1055/S-2006-961429
  6. 10.1248/CPB.47.869

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.