|
Menu

COCONUT Compound

Lupeol

CNP0269715.3 · C30H50O · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameLupeol
IUPAC Name(1~{R},3~{a}~{R},5~{a}~{R},5~{b}~{R},7~{a}~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{R})-1-isopropenyl-3~{a},5~{a},5~{b},8,8,11~{a}-hexamethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysen-9-ol
COCONUT IDCNP0269715.3
CAS545-47-1
InChIKeyMQYXUWHLBZFQQO-QGTGJCAVSA-N
InChIInChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
SMILESC=C(C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Properties

Molecular FormulaC30H50O
Molecular Weight426.73
Exact Mass426.38617
Log P (ALogP)8.02
TPSA20.23
H-Bond Donors / Acceptors1 / 1
Rotatable Bonds1
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.42
NP-likeness3.05

Classification

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

Reported in GR-MAPs Plants

Bacopa monnieri as “Bacopa monnieri” in COCONUT
Centella asiatica as “Centella asiatica” in COCONUT
Tagetes erecta as “Tagetes erecta” in COCONUT
Arabidopsis thaliana as “Arabidopsis thaliana” in COCONUT
Matricaria chamomilla as “Chamomilla recutita” in COCONUT
Daucus carota as “Daucus carota” in COCONUT
Cayratia japonica as “Cayratia japonica” in COCONUT
Salvia officinalis as “Salvia officinalis” in COCONUT
Viola odorata as “Viola odorata” in COCONUT
Tephrosia purpurea as “Tephrosia Purpurea” in COCONUT
Emblica officinalis as “Phyllanthus Emblica” in COCONUT

References (830)

  1. 10.1002/(SICI)1099-1573(199612)10:8<694::AID-PTR923>3.0.CO;2-X
  2. 10.1002/(SICI)1099-1573(199908/09)13:5<433::AID-PTR457>3.0.CO;2-4
  3. 10.1002/1097-458X(200007)38:7<488::AID-MRC704>3.0.CO;2-G
  4. 10.1002/1099-1565(200011/12)11:6<345::AID-PCA540>3.0.CO;2-T
  5. 10.1002/CBDV.200800266
  6. 10.1002/CBDV.200900326
  7. 10.1002/CBDV.201000166
  8. 10.1002/CHIN.198339322
  9. 10.1002/CHIN.198528357
  10. 10.1002/CHIN.199410238
  11. 10.1002/CHIN.200307143
  12. 10.1002/CHIN.200319178
  13. 10.1002/CHIN.200324153
  14. 10.1002/CHIN.200413142
  15. 10.1002/CHIN.200431151
  16. 10.1002/CHIN.200533207
  17. 10.1002/CHIN.200533271
  18. 10.1002/CHIN.200537209
  19. 10.1002/CHIN.200539166
  20. 10.1002/CHIN.200543209
  21. 10.1002/CHIN.200630195
  22. 10.1002/CHIN.200640213
  23. 10.1002/CHIN.201034210
  24. 10.1002/EJOC.200600742
  25. 10.1002/EJOC.201100505
  26. 10.1002/HLCA.19930760712
  27. 10.1002/HLCA.200790187
  28. 10.1002/HLCA.200890115
  29. 10.1002/HLCA.200900431
  30. 10.1002/HLCA.201000138
  31. 10.1002/HLCA.201000207
  32. 10.1002/JCCS.196800006
  33. 10.1002/JCCS.199200061
  34. 10.1002/JCCS.199400028
  35. 10.1002/JCCS.199500076
  36. 10.1002/JCCS.199700056
  37. 10.1002/JCCS.200000075
  38. 10.1002/JCCS.200100154
  39. 10.1002/JCCS.200200019
  40. 10.1002/JCCS.200300178

Showing 40 of 830. 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.