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COCONUT Compound

Cannabidiolic acid

CNP0234351.1 · C22H30O4 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameCannabidiolic acid
IUPAC Name2,4-dihydroxy-3-[(1~{R},6~{R})-6-isopropenyl-3-methyl-cyclohex-2-en-1-yl]-6-pentyl-benzoic acid
COCONUT IDCNP0234351.1
CAS1244-58-2
InChIKeyWVOLTBSCXRRQFR-DLBZAZTESA-N
InChIInChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1
SMILESC=C(C)[C@@H]1CCC(C)=C[C@H]1C1=C(O)C=C(CCCCC)C(C(=O)O)=C1O

Properties

Molecular FormulaC22H30O4
Molecular Weight358.48
Exact Mass358.21441
Log P (ALogP)5.54
TPSA77.76
H-Bond Donors / Acceptors3 / 3
Rotatable Bonds7
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.44
NP-likeness2.26

Classification

NP PathwayPolyketides
NP SuperclassMeroterpenoids
NP ClassCannabinoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassMonoterpenoids

Reported in GR-MAPs Plants

Canabis Sativa as “Cannabis Sativa; Cannabis sativa L.” in COCONUT

References (13)

  1. 10.1002/food.19880321030
  2. 10.1007/S11101-008-9094-4
  3. 10.1007/s11101-008-9094-4
  4. 10.1016/j.lfs.2005.09.011
  5. 10.1021/NP50008A001
  6. 10.1021/NP8002673
  7. 10.1021/np8002673
  8. 10.1074/JBC.271.29.17411
  9. 10.1080/10826079508009265
  10. 10.1093/PCP/PCN150
  11. 10.1111/J.1476-5381.2010.01166.X
  12. 10.3390/biom10060900
  13. 10.3390/molecules25112638

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.