Structure Database (LMSD)
Common Name
3-hydroxy-hexadecanoic acid
Systematic Name
3-hydroxy-hexadecanoic acid
Synonyms
3D model of 3-hydroxy-hexadecanoic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
3-hydroxy Palmitic acid is a form of the 16:0 lipid palmitic acid . The lipid A part of lipopolysaccharides contain various 3-hydroxy fatty acids, making oxylipins such as 3-hydroxy palmitic acid useful as chemical markers of endotoxins.1 In R. solanacearum, 3-hydroxy palmitic acid is converted by an S-adenosyl methionine-dependent methyltransferase to 3-hydroxy palmitic acid methyl ester, which acts as a quorum sensing signal molecule for post-transcriptional modulation of genes involved in virulence.2 Long-chain 3-hydroxy fatty acids, such as 3-hydroxy palmitic acid, are also known to accumulate during long-chain 3-hydroxy-acyl-CoA dehydrogenase and mitochondrial trifunctional protein deficiencies.3 Such accumulation induces oxidative stress, leading to mitochondrial bioenergetics deregulation and eventual multi-organ dysfunction.3
This information has been provided by Cayman Chemical
References
1. Shinohara, M., Nakajima, N., and Uehara, Y. Purification and characterization of a novel esterase (β-hydroxypalmitate methyl ester hydrolase) and prevention of the expression of virulence by Ralstonia solanacearum. J. Appl. Microbiol. 103(1), 152-162 (2007).
2. Tonin, A.M., Amaral, A.U., Busanello, E.N., et al. Mitochondrial bioenergetics deregulation caused by long-chain 3-hydroxy fatty acids accumulating in LCHAD and MTP deficiencies in rat brain: A possible role of mPTP opening as a pathomechanism in these disorders? Biochim. Biophys. Acta 1842(9), 1658-1667 (2014).
String Representations
InChiKey (Click to copy)
CBWALJHXHCJYTE-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)
SMILES (Click to copy)
C(CC(O)CCCCCCCCCCCCC)(=O)O
Other Databases
LIPIDAT ID
1796
HMDB ID
CHEBI ID
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
19
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
309.09
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
4.81
Molar Refractivity
79.85
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Created at
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Updated at
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