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COCONUT Compound

23-hydroxybetulinic acid

CNP0139464.2 · C30H48O4 · View on COCONUT ↗

2D Structure

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Identifiers

Name23-hydroxybetulinic acid
IUPAC Name(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},8~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{R})-9-hydroxy-8-(hydroxymethyl)-1-isopropenyl-5~{a},5~{b},8,11~{a}-tetramethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysene-3~{a}-carboxylic acid
COCONUT IDCNP0139464.2
CAS85999-40-2
InChIKeyHXWLKAXCQLXHML-WGOZWDAUSA-N
InChIInChI=1S/C30H48O4/c1-18(2)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h19-24,31-32H,1,7-17H2,2-6H3,(H,33,34)/t19-,20+,21+,22+,23-,24+,26-,27-,28+,29+,30-/m0/s1
SMILESC=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]12

Properties

Molecular FormulaC30H48O4
Molecular Weight472.71
Exact Mass472.35526
Log P (ALogP)6.06
TPSA77.76
H-Bond Donors / Acceptors3 / 3
Rotatable Bonds3
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.44
NP-likeness3.02

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassLupane triterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassSteroids and steroid derivatives
Chemical SubclassHydroxysteroids

Reported in GR-MAPs Plants

Rosmarinus officinalis as “Rosmarinus Officinalis” in COCONUT
Salvia officinalis as “Salvia officinalis” in COCONUT

References (8)

  1. 10.1016/0031-9422(94)00445-Y
  2. 10.1016/0031-9422(96)00043-X
  3. 10.1016/J.JEP.2010.02.004
  4. 10.1016/J.PHYTOCHEM.2005.04.041
  5. 10.1016/S0024-3205(02)02176-8
  6. 10.1016/S0031-9422(01)00180-7
  7. 10.1021/NP200359V
  8. 10.1055/S-2002-20254

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.