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COCONUT Compound

Acetobetulinic acid

CNP0233093.1 · C32H50O4 · View on COCONUT ↗

2D Structure

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Identifiers

NameAcetobetulinic acid
IUPAC Name(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{R})-9-acetoxy-1-isopropenyl-5~{a},5~{b},8,8,11~{a}-pentamethyl-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 IDCNP0233093.1
CAS10376-50-8
InChIKeyACWNTJJUZAIOLW-BWXYOZBYSA-N
InChIInChI=1S/C32H50O4/c1-19(2)21-11-16-32(27(34)35)18-17-30(7)22(26(21)32)9-10-24-29(6)14-13-25(36-20(3)33)28(4,5)23(29)12-15-31(24,30)8/h21-26H,1,9-18H2,2-8H3,(H,34,35)/t21-,22+,23-,24+,25-,26+,29-,30+,31+,32-/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](OC(C)=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Properties

Molecular FormulaC32H50O4
Molecular Weight498.75
Exact Mass498.37091
Log P (ALogP)7.66
TPSA63.60
H-Bond Donors / Acceptors1 / 3
Rotatable Bonds3
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.32
NP-likeness3.01

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

Plantago ovata as “Plantago ovata” in COCONUT

References (11)

  1. 10.1016/J.BMCL.2010.10.058
  2. 10.1016/J.PHYTOL.2011.05.002
  3. 10.1016/S0367-326X(00)00155-6
  4. 10.1021/NP0502793
  5. 10.1021/NP50054A031
  6. 10.1021/NP9606052
  7. 10.1021/NP990227B
  8. 10.1021/np50054a031
  9. 10.1248/CPB.39.3276
  10. 10.1248/CPB.58.971
  11. 10.5012/BKCS.2010.31.01.199

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.