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COCONUT Compound

Isovaltrate

CNP0302292.1 · C22H30O8 · View on COCONUT ↗

2D Structure

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Identifiers

NameIsovaltrate
IUPAC Name[(1~{S},6~{S},7~{R},7~{a}~{S})-6-acetoxy-1-(3-methylbutanoyloxy)spiro[6,7~{a}-dihydro-1~{H}-cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate
COCONUT IDCNP0302292.1
CAS31078-10-1
InChIKeyXLACUABANMZLCJ-KVJIRVJXSA-N
InChIInChI=1S/C22H30O8/c1-12(2)6-18(24)26-9-15-10-27-21(30-19(25)7-13(3)4)20-16(15)8-17(29-14(5)23)22(20)11-28-22/h8,10,12-13,17,20-21H,6-7,9,11H2,1-5H3/t17-,20+,21-,22+/m0/s1
SMILESCC(=O)O[C@H]1C=C2C(COC(=O)CC(C)C)=CO[C@@H](OC(=O)CC(C)C)[C@@H]2[C@@]12CO2

Properties

Molecular FormulaC22H30O8
Molecular Weight422.47
Exact Mass422.19407
Log P (ALogP)2.66
TPSA100.66
H-Bond Donors / Acceptors0 / 8
Rotatable Bonds8
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.33
NP-likeness2.35

Classification

NP PathwayTerpenoids
NP SuperclassMonoterpenoids
NP ClassIridoids monoterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassMonoterpenoids

Reported in GR-MAPs Plants

Valeriana jatamansi as “Valeriana Jatamansi” in COCONUT

References (29)

  1. 10.1002/(SICI)1099-1565(199603)7:2<76::AID-PCA288>3.0.CO;2-L
  2. 10.1002/(SICI)1099-1565(200005/06)11:3<179::AID-PCA515>3.0.CO;2-5
  3. 10.1002/HLCA.201100465
  4. 10.1002/PCA.2800050605
  5. 10.1002/food.19880321030
  6. 10.1007/BF00233361
  7. 10.1007/BF02097255
  8. 10.1016/0031-9422(74)80247-5
  9. 10.1016/0031-9422(80)87018-X
  10. 10.1016/0031-9422(95)91889-9
  11. 10.1016/0378-8741(88)90123-7
  12. 10.1016/S0031-9422(00)81597-6
  13. 10.1016/S0031-9422(00)83011-3
  14. 10.1016/S0944-7113(98)80032-9
  15. 10.1021/NP0104267
  16. 10.1021/NP0203335
  17. 10.1021/NP0704553
  18. 10.1021/NP50012A004
  19. 10.1021/NP50036A004
  20. 10.1021/NP50037A003
  21. 10.1021/np0704553
  22. 10.1055/S-2001-18344
  23. 10.1055/S-2006-957392
  24. 10.1055/S-2006-959740
  25. 10.1055/S-2006-961613
  26. 10.1055/S-2007-969605
  27. 10.1055/S-2007-969817
  28. 10.2478/v10136-009-0002-z
  29. 10.3109/13880208709060916

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.