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Record Information
Version3.6
Creation Date2006-08-13 07:49:56 UTC
Update Date2013-04-25 20:42:27 UTC
HMDB IDHMDB03942
Secondary Accession NumbersNone
Metabolite Identification
Common Name(S)-Hydroxyhexanoyl-CoA
Description(S)-Hydroxyhexanoyl-CoA is an intermediate in fatty acid metabolism, being the substrate of the enzymes beta-hydroxyacyl-CoA dehydrogenase and 3-hydroxyacyl-CoA dehydrogenase [EC 1.1.1.211-1.1.1.35]; (S)-Hydroxyhexanoyl-CoA is an intermediate in fatty acid elongation in mitochondria, the substrate of the enzymes enoyl-CoA hydratase and long-chain-enoyl-CoA hydratase [EC 4.2.1.17-4.2.1.74]. (KEGG).
Structure
Thumb
Synonyms
  1. (S)-3-Hydroxyhexanoyl-CoA
  2. (S)-3-Hydroxyhexanoyl-Coenzyme A
  3. S-(3-Hydroxyhexanoate
  4. S-(3-Hydroxyhexanoate)CoA
  5. S-(3-Hydroxyhexanoate)Coenzyme A
  6. S-(3-Hydroxyhexanoic acid
  7. [R,S]-Lactyl CoA
  8. [R,S]-Lactyl Coenzyme A
Chemical FormulaC27H46N7O18P3S
Average Molecular Weight881.677
Monoisotopic Molecular Weight881.183287929
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number5060-32-2
SMILES
CCC[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1S/C27H46N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-16,20-22,26,35,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t15-,16+,20+,21+,22?,26+/m0/s1
InChI KeyVAAHKRMGOFIORX-DWUFXMDISA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassAcyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Fatty acyl CoAs(KEGG)
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Disaccharide Phosphate
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Mixed Pentose/Hexose Disaccharide
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct ParentAcyl CoAs
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.019Not Available
Predicted Properties
PropertyValueSource
water solubility3.71 g/LALOGPS
logP-0.28ALOGPS
logP-6.2ChemAxon
logS-2.4ALOGPS
pKa (strongest acidic)0.83ChemAxon
pKa (strongest basic)4.95ChemAxon
physiological charge-4ChemAxon
hydrogen acceptor count18ChemAxon
hydrogen donor count10ChemAxon
polar surface area383.86ChemAxon
rotatable bond count24ChemAxon
refractivity192.15ChemAxon
polarizability78.5ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid Elongation In MitochondriaSMP00054map00062
Fatty acid MetabolismSMP00051map00071
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023261
KNApSAcK IDNot Available
Chemspider ID389507
KEGG Compound IDC05268
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03942
Metagene LinkHMDB03942
METLIN IDNot Available
PubChem Compound440609
PDB IDNot Available
ChEBI ID28276
References
Synthesis ReferenceTamvakopoulos, Constantine S.; Anderson, Vernon E. Detection of acyl-coenzyme A thioester intermediates of fatty acid b-oxidation as the N-acylglycines by negative-ion chemical ionization gas chromatography mass spectrometry. Analytical Biochemistry
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dalluge JJ, Gort S, Hobson R, Selifonova O, Amore F, Gokarn R: Separation and identification of organic acid-coenzyme A thioesters using liquid chromatography/electrospray ionization-mass spectrometry. Anal Bioanal Chem. 2002 Nov;374(5):835-40. Epub 2002 Oct 8. Pubmed: 12434239
  2. Klees AG, Linder D, Buckel W: 2-Hydroxyglutaryl-CoA dehydratase from Fusobacterium nucleatum (subsp. nucleatum): an iron-sulfur flavoprotein. Arch Microbiol. 1992;158(4):294-301. Pubmed: 1417419
  3. Kim J, Hetzel M, Boiangiu CD, Buckel W: Dehydration of (R)-2-hydroxyacyl-CoA to enoyl-CoA in the fermentation of alpha-amino acids by anaerobic bacteria. FEMS Microbiol Rev. 2004 Oct;28(4):455-68. Pubmed: 15374661
  4. Hofmeister AE, Buckel W: (R)-lactyl-CoA dehydratase from Clostridium propionicum. Stereochemistry of the dehydration of (R)-2-hydroxybutyryl-CoA to crotonyl-CoA. Eur J Biochem. 1992 Jun 1;206(2):547-52. Pubmed: 1597194
  5. Kuchta RD, Hanson GR, Holmquist B, Abeles RH: Fe-S centers in lactyl-CoA dehydratase. Biochemistry. 1986 Nov 18;25(23):7301-7. Pubmed: 3026450
  6. Kuchta RD, Abeles RH: Lactate reduction in Clostridium propionicum. Purification and properties of lactyl-CoA dehydratase. J Biol Chem. 1985 Oct 25;260(24):13181-9. Pubmed: 4055736
  7. Sokatch JR: Alanine and aspartate formation during growth on valine-C14 by Pseudomonas aeruginosa. J Bacteriol. 1966 Jul;92(1):72-5. Pubmed: 4957438
  8. Megraw RE, Reeves HC, Ajl SJ: Formation of lactyl-coenzyme A and pyruvyl-coenzyme A from lactic acid by Escherichia coli. J Bacteriol. 1965 Oct;90(4):984-8. Pubmed: 5321404

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:
HSD17B10
Uniprot ID:
Q99714
Molecular weight:
25983.695
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
(S)-Hydroxyhexanoyl-CoA + NAD → 3-Oxohexanoyl-CoA + NADH + Hydrogen Iondetails
(S)-Hydroxyhexanoyl-CoA → trans-2-Hexenoyl-CoA + Waterdetails
General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:
HADH
Uniprot ID:
Q16836
Molecular weight:
36035.11
Reactions
(S)-Hydroxyhexanoyl-CoA + NAD → 3-Oxohexanoyl-CoA + NADH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:
ECHS1
Uniprot ID:
P30084
Molecular weight:
31387.085
Reactions
(S)-Hydroxyhexanoyl-CoA → trans-2-Hexenoyl-CoA + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
(S)-Hydroxyhexanoyl-CoA + NAD → 3-Oxohexanoyl-CoA + NADH + Hydrogen Iondetails
(S)-Hydroxyhexanoyl-CoA → trans-2-Hexenoyl-CoA + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme acting on the peroxisomal beta-oxidation pathway for fatty acids. Catalyzes the formation of 3-ketoacyl-CoA intermediates from both straight-chain and 2-methyl-branched-chain fatty acids.
Gene Name:
HSD17B4
Uniprot ID:
P51659
Molecular weight:
79685.715