Structure Database (LMSD)

Common Name
Behenic acid
Systematic Name
docosanoic acid
Synonyms
  • C22:0
LM ID
LMFA01010022
Formula
Exact Mass
Calculate m/z
340.33413
Sum Composition
Status
Curated



Classification

Biological Context

Docosanoic acid is a long-chain saturated fatty acid. It has been found in peanut and M. oleifera seed oils.1,2 It inhibits the double-stranded DNA binding activity of p53 through a direct interaction with the DNA binding domain (Kd = 12 nM).3 Docosanoic acid inhibits rat DNA polymerase β and human DNA polymerase λ activity in cell-free enzyme assays when used at a concentration of 100 µM and inhibits human DNA topoisomerase I and II relaxation activity at a concentration of 25 µM.4 Liver levels of docosanoic acid are reduced in rats fed a high-fat or a high-fat high-cholesterol diet but not a high-cholesterol diet.5 Formulations containing docosanoic acid have been used in hair conditioner and moisturizers.

This information has been provided by Cayman Chemical

References

3. Dean, L.L., and Sanders, T.H. Hexacosanoic acid and other very long-chain fatty acids in peanut seed oil. Plant Genet. Resour. 7(3), 252-256 (2009).

Reactions

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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
UKMSUNONTOPOIO-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)
SMILES (Click to copy)
C(CCCCCCCCCCCCC(=O)O)CCCCCCCC

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0022
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 20
Van der Waals Molecular Volume 404.10
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 7.89
Molar Refractivity 105.65

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Created at
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Updated at
25th Apr 2022