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COCONUT Compound

celastrol

CNP0199266.2 · C29H38O4 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Namecelastrol
IUPAC Name(2~{R},4~{a}~{S},6~{a}~{R},6~{a}~{S},14~{a}~{S},14~{b}~{R})-10-hydroxy-2,4~{a},6~{a},6~{a},9,14~{a}-hexamethyl-11-oxo-1,3,4,5,6,13,14,14~{b}-octahydropicene-2-carboxylic acid
COCONUT IDCNP0199266.2
CAS34157-83-0, 34157-83-0 (castrol)
InChIKeyKQJSQWZMSAGSHN-JJWQIEBTSA-N
InChIInChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
SMILESCC1=C(O)C(=O)C=C2C1=CC=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@](C)(C(=O)O)CC[C@]3(C)CC[C@]12C

Properties

Molecular FormulaC29H38O4
Molecular Weight450.62
Exact Mass450.27701
Log P (ALogP)6.70
TPSA74.60
H-Bond Donors / Acceptors2 / 3
Rotatable Bonds1
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.47
NP-likeness3.33

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP Class
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTriterpenoids

Reported in GR-MAPs Plants

Centella asiatica as “Centella asiatica” in COCONUT

References (44)

  1. 10.1002/HLCA.200900426
  2. 10.1002/PCA.626
  3. 10.1002/PS.953
  4. 10.1002/pca.626
  5. 10.1016/0031-9422(88)83123-6
  6. 10.1016/0031-9422(90)80182-G
  7. 10.1016/0031-9422(90)80182-g
  8. 10.1016/0031-9422(94)00916-H
  9. 10.1016/0031-9422(96)00886-2
  10. 10.1016/0040-4020(96)00497-8
  11. 10.1016/0305-1978(86)90005-0
  12. 10.1016/0968-0896(96)00078-8
  13. 10.1016/J.BMCL.2007.12.016
  14. 10.1016/J.BMCL.2010.01.152
  15. 10.1016/J.FCT.2010.11.044
  16. 10.1016/J.PHYTOCHEM.2010.06.023
  17. 10.1016/J.PHYTOCHEM.2011.03.018
  18. 10.1016/J.PHYTOCHEM.2011.11.023
  19. 10.1016/S0031-9422(00)00007-8
  20. 10.1016/S0031-9422(00)00144-8
  21. 10.1016/S0031-9422(00)00285-5
  22. 10.1016/S0031-9422(96)00858-8
  23. 10.1016/S0031-9422(96)00859-X
  24. 10.1016/S0031-9422(97)00048-4
  25. 10.1016/S0031-9422(97)00288-4
  26. 10.1016/S0031-9422(98)00300-8
  27. 10.1016/S0031-9422(99)00557-9
  28. 10.1016/S0040-4020(98)00835-7
  29. 10.1016/j.bmc.2012.06.050
  30. 10.1016/j.phytochem.2018.01.009
  31. 10.1021/JO00169A030
  32. 10.1021/NP010428R
  33. 10.1021/NP030241V
  34. 10.1021/NP030241V.S001
  35. 10.1021/NP200029Q
  36. 10.1021/NP50103A001
  37. 10.1021/NP900820P
  38. 10.1021/NP9704157
  39. 10.1039/9781847555649-00238
  40. 10.1039/P19830002845

Showing 40 of 44. 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.