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COCONUT Compound

Acetylursolic acid

CNP0156134.2 · C32H50O4 · View on COCONUT ↗

2D Structure

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Identifiers

NameAcetylursolic acid
IUPAC Name(1~{S},2~{R},4~{a}~{S},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},10~{S},12~{a}~{R},14~{b}~{S})-10-acetoxy-1,2,6~{a},6~{b},9,9,12~{a}-heptamethyl-2,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydro-1~{H}-picene-4~{a}-carboxylic acid
COCONUT IDCNP0156134.2
CAS7372-30-7
InChIKeyPHFUCJXOLZAQNH-OTMOLZNZSA-N
InChIInChI=1S/C32H50O4/c1-19-11-16-32(27(34)35)18-17-30(7)22(26(32)20(19)2)9-10-24-29(6)14-13-25(36-21(3)33)28(4,5)23(29)12-15-31(24,30)8/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)/t19-,20+,23+,24-,25+,26+,29+,30-,31-,32+/m1/s1
SMILESCC(=O)O[C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C(=O)O)CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C

Properties

Molecular FormulaC32H50O4
Molecular Weight498.75
Exact Mass498.37091
Log P (ALogP)7.66
TPSA63.60
H-Bond Donors / Acceptors1 / 3
Rotatable Bonds2
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.31
NP-likeness3.14

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassUrsane and Taraxastane triterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTriterpenoids

Reported in GR-MAPs Plants

Callicarpa macrophylla as “Callicarpa Macrophylla” in COCONUT
Rosmarinus officinalis as “Rosmarinus officinalis” in COCONUT
Salvia officinalis as “Salvia officinalis” in COCONUT
Eucalyptus citriodora as “Eucalyptus citriodora” in COCONUT

References (89)

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  2. 10.1002/CBDV.201000228
  3. 10.1002/JSSC.201300794
  4. 10.1007/BF00567057
  5. 10.1007/BF02973871
  6. 10.1007/S10600-009-9411-1
  7. 10.1007/S11418-006-0015-9
  8. 10.1007/S11418-008-0267-7
  9. 10.1007/S11746-011-1770-7
  10. 10.1016/0031-9422(83)80050-8
  11. 10.1016/0031-9422(83)80162-9
  12. 10.1016/0031-9422(92)80123-V
  13. 10.1016/0031-9422(92)83634-B
  14. 10.1016/J.BMCL.2010.10.058
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  18. 10.1016/J.PHYMED.2008.01.003
  19. 10.1016/J.PHYTOCHEM.2004.12.026
  20. 10.1016/J.PHYTOCHEM.2005.11.024
  21. 10.1016/J.PHYTOCHEM.2007.01.008
  22. 10.1016/J.PHYTOCHEM.2009.04.019
  23. 10.1016/J.PHYTOCHEM.2009.05.011
  24. 10.1016/J.TET.2010.05.010
  25. 10.1016/S0031-9422(00)00007-8
  26. 10.1016/S0031-9422(00)81179-6
  27. 10.1016/S0031-9422(00)81749-5
  28. 10.1016/S0031-9422(00)82359-6
  29. 10.1016/S0031-9422(00)91468-7
  30. 10.1016/S0031-9422(00)94210-9
  31. 10.1016/S0031-9422(00)94767-8
  32. 10.1016/S0031-9422(97)00492-5
  33. 10.1016/S0031-9422(97)01004-2
  34. 10.1016/S0031-9422(97)01020-0
  35. 10.1016/S0031-9422(97)01061-3
  36. 10.1016/S0031-9422(98)80075-7
  37. 10.1016/S0031-9422(99)00167-3
  38. 10.1016/S0031-9422(99)00270-8
  39. 10.1016/S0031-9422(99)00557-9
  40. 10.1016/S0305-1978(98)00061-1

Showing 40 of 89. See all references on COCONUT.

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.