Structure Database (LMSD)

Common Name
DL-2-hydroxy stearic acid
Systematic Name
2-hydroxy-octadecanoic acid
Synonyms
LM ID
LMFA02000120
Formula
C18H36O3
Exact Mass
Calculate m/z
300.266445
Sum Composition
FA 18:0;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]
Octadecanoids [FA02]
Other Octadecanoids [FA0200]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]

Biological Context

2-hydroxy Stearic acid is a naturally occurring hydroxylated fatty acid that has been found in humans and U. armoricana.1,2,3 It reduces growth of Ehrlich ascites tumor (EAT) cells in vitro when used at a concentration of 100 μM.4 Levels of 2-hydroxy stearic acid are elevated in human joint synovial fluid after ankle fracture and in patients with Buruli ulcer disease.2,3 [Matreya, LLC. Catalog No. 1707]

This information has been provided by Cayman Chemical

References

1. Kendel, M., Wielgosz-Collin, G., Bertrand, S., et al. Lipid composition, fatty acids and sterols in the seaweeds Ulva armoricana, and Solieria chordalis from Brittany (France): An analysis from nutritional, chemotaxonomic, and antiproliferative activity perspectives. Mar. Drugs 13(9), 5606-5628 (2015).
2. Leimer, E.M., Pappan, K.L., Nettles, D.L., et al. Lipid profile of human synovial fluid following intra-articular ankle fracture. J. Orthop. Res. 35(3), 657-666 (2017).
3. Niang, F., Sarfo, F.S., Frimpong, M., et al. Metabolomic profiles delineate mycolactone signature in Buruli ulcer disease. Sci. Rep. 5:17693, (2015).
4. Kusmoto, K., Kageyama, K., Matsuda, T., et al. Effects of ethyl-esterization, chain-lengths, unsaturation degrees, and hyperthermia on carcinostatic effect of omega-hydroxylated fatty acids. Exp. Oncol. 29(2), 106-110 (2007).

String Representations

InChiKey (Click to copy)
KIHBGTRZFAVZRV-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C18H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h17,19H,2-16H2,1H3,(H,20,21)
SMILES (Click to copy)
C(CCCCCCCCCCCCCCC)C(O)C(=O)O

Other Databases

HMDB ID
HMDB0062549
CHEBI ID
19660
PubChem CID
69417
PlantFA ID
10262
SwissLipids ID
SLM:000000831
Cayman ID
24590

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 343.69
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.59
Molar Refractivity 89.08

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Updated at
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