Structure Database (LMSD)

Common Name
Tricosylic acid
Systematic Name
Tricosanoic acid
Synonyms
  • C23:0
LM ID
LMFA01010023
Formula
C23H46O2
Exact Mass
Calculate m/z
354.34978
Sum Composition
FA 23:0
Status
Curated
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Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Straight chain fatty acids [FA0101]

Biological Context

Tricosanoic acid is a naturally occurring saturated fatty acid that has been found in various edible mushroom species.1 It inhibits lysis of human erythrocytes induced by S. aureus delta toxin in a concentration-dependent manner.2 Tricosanoic acid levels are decreased in the sebum of patients with papulopustular rosacea and increased in malignant, but not adjacent nonmalignant, prostate tissue in patients with prostate cancer.3,4 Tricosanoic acid has been used as an internal standard for the quantification of fatty acids in chicken egg yolk.5

This information has been provided by Cayman Chemical

References

1. Wang, Y., Sunwoo, H., Cherian, G., et al. Fatty acid determination in chicken egg yolk: A comparison of different methods. Poult. Sci. 79(8), 1168-1171 (2000).
2. Ní Raghallaigh, S., Bender, K., Lacey, N., et al. The fatty acid profile of the skin surface lipid layer in papulopustular rosacea. Br. J. Dermatol. 166(2), 279-287 (2012).
3. Ribeiro, B., Guedes de Pinho, P., Andrade, P.B., et al. Fatty acid composition of wild edible mushrooms species: A comparative study. Microchem. J. 93(1), 29-35 (2009).
4. Jung, K., Reszka, R., Kamlage, B., et al. Tissue metabolite profiling identifies differentiating and prognostic biomarkers for prostate carcinoma. Int. J. Cancer 133(12), 2914-2924 (2013).
5. Kapral, F.A. Effect of fatty acids on Staphylococcus aureus delta-toxin hemolytic activity. Infect. Immun. 13(1), 114-119 (1976).

Reactions

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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)
XEZVDURJDFGERA-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C23H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(24)25/h2-22H2,1H3,(H,24,25)
SMILES (Click to copy)
C(CCCCCCCCCCCCC(=O)O)CCCCCCCCC

Other Databases

HMDB ID
HMDB0001160
CHEBI ID
42394
LIPIDBANK ID
DFA0023
PubChem CID
17085
PlantFA ID
10164
SwissLipids ID
SLM:000001128
Cayman ID
26867
PDB ID
F23

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 21
Van der Waals Molecular Volume 421.40
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 8.28
Molar Refractivity 110.27

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Created at
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Updated at
25th Apr 2022