Structure Database (LMSD)

Common Name
2-hydroxy behenic
Systematic Name
2-hydroxy-docosanoic acid
Synonyms
LM ID
LMFA01050077
Formula
C22H44O3
Exact Mass
Calculate m/z
356.329046
Sum Composition
FA 22:0;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]
Docosanoids [FA04]

Biological Context

2-hydroxy Docosanoic acid is a hydroxylated fatty acid that has been found in the mature black epidermis of the Antarctic minke whale, as the N-acyl chain of galactosylceramides in mouse brain, and the inner bark of E. globulus.1,2,3 It is upregulated in prostate carcinoma tissue as compared to normal prostate epithelium.4 [Matreya, LLC. Catalog No. 1711]

This information has been provided by Cayman Chemical

References

1. Alderson, N.L., Maldonado, E.N., Kern, M.J., et al. FA2H-dependent fatty acid 2-hydroxylation in postnatal mouse brain. J. Lipid Res. 47(12), 2772-2780 (2006).
2. Yunoki, K., Ishikawa, H., Fukui, Y., et al. Chemical properties of epidermal lipids, especially sphingolipids, of the Antarctic minke whale. Lipids 43(2), 151-159 (2008).
3. Freire, C.S.R., Silvestre, A.J.D., Neto, C.P., et al. Lipophilic extractives of the inner and outer barks of Eucalyptus globulus. Holzforschung 56(4), 372-379 (2002).
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).

String Representations

InChiKey (Click to copy)
RPGJJWLCCOPDAZ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C22H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(23)22(24)25/h21,23H,2-20H2,1H3,(H,24,25)
SMILES (Click to copy)
C(CCCCCCCCCCCC(O)C(=O)O)CCCCCCCC

Other Databases

HMDB ID
HMDB0061660
CHEBI ID
76980
LIPIDBANK ID
DFA0343
PubChem CID
193484
PlantFA ID
10266
SwissLipids ID
SLM:000000828
Cayman ID
24594

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 20
Van der Waals Molecular Volume 412.89
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 7.15
Molar Refractivity 107.55

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Updated at
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