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COCONUT Compound

Cucurbitacin E

CNP0210262.2 · C32H44O8 · View on COCONUT ↗

2D Structure

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Identifiers

NameCucurbitacin E
IUPAC Name[(~{E},5~{R})-5-[(8~{S},9~{R},10~{R},13~{R},14~{S},16~{R},17~{R})-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7~{H}-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-1,1-dimethyl-4-oxo-hex-2-enyl] acetate
COCONUT IDCNP0210262.2
CAS18444-66-1
InChIKeyNDYMQXYDSVBNLL-MUYMLXPFSA-N
InChIInChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1
SMILESCC(=O)OC(C)(C)/C=C/C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

Properties

Molecular FormulaC32H44O8
Molecular Weight556.70
Exact Mass556.30362
Log P (ALogP)4.19
TPSA138.20
H-Bond Donors / Acceptors3 / 8
Rotatable Bonds5
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.26
NP-likeness3.15

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassCucurbitane triterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassSteroids and steroid derivatives
Chemical SubclassCucurbitacins

Reported in GR-MAPs Plants

Bacopa monnieri as “Bacopa Monnieri” in COCONUT

References (35)

  1. 10.1002/(SICI)1099-1565(200003/04)11:2<121::AID-PCA493>3.0.CO;2-9
  2. 10.1002/9780470744307.gat218
  3. 10.1002/CHIN.200434239
  4. 10.1002/MRC.1570
  5. 10.1002/food.19880321030
  6. 10.1002/mrc.1570
  7. 10.1002/ptr.2650090302
  8. 10.1007/BF00987375
  9. 10.1007/s00011-013-0598-z
  10. 10.1016/0031-9422(75)85356-8
  11. 10.1016/0031-9422(77)84014-4
  12. 10.1016/0031-9422(88)80472-2
  13. 10.1016/0031-9422(88)84112-8
  14. 10.1016/0040-4020(76)85214-3
  15. 10.1016/J.FITOTE.2011.08.002
  16. 10.1016/J.FITOTE.2012.09.016
  17. 10.1016/J.PHYTOCHEM.2007.03.013
  18. 10.1016/S0024-3205(03)00602-7
  19. 10.1016/S0040-4020(01)91826-5
  20. 10.1016/S0367-326X(00)00256-2
  21. 10.1021/ACS.JNATPROD.8B00461
  22. 10.1021/JF00103A051
  23. 10.1021/NP50112A015
  24. 10.1021/NP50113A004
  25. 10.1021/OL036469R
  26. 10.1055/S-2006-957755
  27. 10.1055/S-2006-959668
  28. 10.1080/1057563021000042329
  29. 10.1080/10575639908048799
  30. 10.1248/CPB.49.1377
  31. 10.1248/CPB.52.345
  32. 10.1248/CPB.58.747
  33. 10.1271/BBB1961.50.2831
  34. 10.3109/10408447709082600
  35. 10.4268/CJCMM20151817

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.