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Human Metabolome Database Version 3.5

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Showing metabocard for (S)-Hydroxyoctanoyl-CoA (HMDB03940)

Record Information
Version 3.5
Creation Date 2006-08-13 01:48:28 -0600
Update Date 2013-02-08 17:12:50 -0700
HMDB ID HMDB03940
Secondary Accession Numbers None
Metabolite Identification
Common Name (S)-Hydroxyoctanoyl-CoA
Description Coenzyme A is notable for its role in the synthesis and oxidation of fatty acids. Since coenzyme A is chemically a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. It assists in transferring fatty acids from the cytoplasm to mitochondria. Specifically (S)-Hydroxyoctanoyl-CoA is involved in fatty acid metabolism. It is the product of a reaction between 3-Oxooctanoyl-CoA and two enzymes; 3-hydroxyacyl-CoA Dehydrogenase and long-chain- 3-hydroxyacyl-CoA dehydrogenase.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (S)-3-Hydroxyoctanoyl-CoA
  2. (S)-3-Hydroxyoctanoyl-Coenzyme A
Chemical Formula C29H50N7O18P3S
Average Molecular Weight 909.73
Monoisotopic Molecular Weight 909.214588057
IUPAC Name {[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyoctanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name [(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyoctanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number 79171-48-5
SMILES [H][C@](O)(CCCCC)CC(=O)SCCNC(=O)CCNC(=O)[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier InChI=1S/C29H50N7O18P3S/c1-4-5-6-7-17(37)12-20(39)58-11-10-31-19(38)8-9-32-27(42)24(41)29(2,3)14-51-57(48,49)54-56(46,47)50-13-18-23(53-55(43,44)45)22(40)28(52-18)36-16-35-21-25(30)33-15-34-26(21)36/h15-18,22-24,28,37,40-41H,4-14H2,1-3H3,(H,31,38)(H,32,42)(H,46,47)(H,48,49)(H2,30,33,34)(H2,43,44,45)/t17-,18+,22?,23-,24-,28+/m0/s1
InChI Key ATVGTMKWKDUCMS-FZQVHTIWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Disaccharide Phosphate
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Other Mixed Disaccharide
  • Oxolane
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent Acyl CoAs
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -2.119 Not Available
Predicted Properties
Property Value Source
Water Solubility 3.44 g/L ALOGPS
LogP -0.03 ALOGPS
LogP -5.3 ChemAxon
LogS -2.42 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 10 ChemAxon
Polar Surface Area 383.86 A2 ChemAxon
Rotatable Bond Count 26 ChemAxon
Refractivity 201.36 ChemAxon
Polarizability 84.67 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Fatty acid Metabolism SMP00051 map00071 Link_out
Fatty Acid Elongation In Mitochondria SMP00054 map00062 Link_out
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids SMP00480 Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids SMP00481 Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023259
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C05266 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03940 Link_out
Metagene Link HMDB03940 Link_out
METLIN ID Not Available
PubChem Compound 53477508 Link_out
PDB ID Not Available
ChEBI ID 28632 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: 3-hydroxyacyl-CoA dehydrogenase type-2
Reactions:
  • (2S,3S)-3-hydroxy-2-methylbutanoyl-CoA + NAD+ = 2-methylacetoacetyl-CoA + NADH + H+ [RN:R04203]
Gene Name: HSD17B10
Uniprot ID: Q99714 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal bifunctional enzyme
Reactions:
  • (3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA [RN:R04100]
Gene Name: EHHADH
Uniprot ID: Q08426 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial
Reactions:
  • (S)-3-hydroxyacyl-CoA + NAD+ = 3-oxoacyl-CoA + NADH + H+ [RN:R01778]
Gene Name: HADH
Uniprot ID: Q16836 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Enoyl-CoA hydratase, mitochondrial
Reactions:
  • (3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H2O [RN:R02685 R07314]
Gene Name: ECHS1
Uniprot ID: P30084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit alpha, mitochondrial
Reactions:
  • (3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H2O [RN:R02685 R07314]
Gene Name: HADHA
Uniprot ID: P40939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal multifunctional enzyme type 2
Reactions:
  • (24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestanoyl- CoA = (24E)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-enoyl-CoA + H2O [RN:R04813]
Gene Name: HSD17B4
Uniprot ID: P51659 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA