Showing Metabocard for (3S)-hydroxyhexadecanoyl-CoA (BASm0004330)

Not AvailableNot AvailableNot Available

Common Name

(3s)-hydroxyhexadecanoyl-coa

Description

(S)-3-Hydroxyhexadecanoyl-CoA is a beta-oxidation intermediate derivative of palmitoyl-CoA and the substrate of the enzyme peroxisomal acyl-CoA thioesterase 2 (PTE-2, EC 3.1.2.2), which is localized in the peroxisome. The peroxisomal beta-oxidation system contains two sets of enzymes, one of which is involved in the oxidation of branched chain fatty acids and intermediates in the hepatic bile acid biosynthetic pathway and consists of one or two branched-chain acyl-CoA oxidase(s), a D-specific bifunctional protein and the sterol carrier-like protein x (SCPx). Peroxisomes are cellular organelles present in all eukaryotic cells. They play an indispensable role in the metabolism of a variety of lipids including very long-chain fatty acids, dicarboxylic fatty acids, bile acids, prostaglandins, leukotrienes, thromboxanes, pristanic acid, and xenobiotic fatty acids. (S)-3-Hydroxyhexadecanoyl-CoA may accumulate intracellularly in certain long-chain fatty acid/j-oxidation deficiencies. Succinate-driven synthesis of ATP from ADP and phosphate is progressively inhibited by increasing concentrations of (S)-3-Hydroxyhexadecanoyl-CoA. (PMID: 11673457 , 8739955 , 7662716 ).

Structure

Molecular Formula

C₃₇H₆₆N₇O₁₈P₃S

Average Mass

1021.94200

Monoisotopic Mass

1021.33979

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

35106-50-4

SMILES

CCCCCCCCCCCCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]

InChI Identifier

InChI=1S/C37H66N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-26,30-32,36,45,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t25-,26+,30+,31+,32-,36+/m0/s1

InChI Key

DEHLMTDDPWDRDR-BCIKBWLNSA-N

CHEBI ID

CHEBI:62613

HMDB ID

HMDB0003932

MiMeDB ID

MMDBc0032995

Pathways

Name	SMPDB/PathBank
Fatty acid Metabolism
Fatty Acid Elongation In Mitochondria
Ethylmalonic Encephalopathy
Glutaric Aciduria Type I
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids
Carnitine palmitoyl transferase deficiency (I)
Long chain acyl-CoA dehydrogenase deficiency (LCAD)
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)
Carnitine palmitoyl transferase deficiency (II)
Medium chain acyl-coa dehydrogenase deficiency (MCAD)
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)
Trifunctional protein deficiency

State

Solid

Water Solubility

Not Available

logS

Not Available

pKa (Strongest Acidic)

Not Available

pKa (Strongest Basic)

Not Available

Hydrogen Acceptor Count

Not Available

Hydrogen Donor Count

Not Available

Rotatable Bond Count

Not Available

Physiological Charge

Not Available

Formal Charge

Not Available

Polarizability

Not Available

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