LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Cannabinolic acid

Systematic Name

1-hydroxy-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-2-carboxylic acid

Synonyms

CBNA

LM ID

LMPK13120007

Formula

C₂₂H₂₆O₄

Exact Mass

Calculate m/z

354.18311

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Cannabis sativa (#3483)

Magnoliopsida (#3398)

Hashish. IV. The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids.,
Tetrahedron, 1965

Pubmed ID: 5879350

DOI: 10.1016/0040-4020(65)80064-3

String Representations

InChiKey (Click to copy)

KXKOBIRSQLNUPS-UHFFFAOYSA-N

InChi (Click to copy)

InChI=1S/C22H26O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h9-12,23H,5-8H2,1-4H3,(H,24,25)

SMILES (Click to copy)

C12=C(C(C)(OC3C=C(C(C(O)=O)=C(O)C=31)CCCCC)C)C=CC(C)=C2

Other Databases

PubChem CID

3081990

Cayman ID

37688

Calculated Physicochemical Properties

Heavy Atoms 26

Rings 3

Aromatic Rings 2

Rotatable Bonds 5

Van der Waals Molecular Volume 346.96

Topological Polar Surface Area 68.83

Hydrogen Bond Donors 2

Hydrogen Bond Acceptors 4

logP 5.43

Molar Refractivity 102.12

Admin

Created at

31st Jul 2024

Updated at