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Human Metabolome Database Version 3.5

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Showing metabocard for 3-Oxooctanoyl-CoA (HMDB03941)

Record Information
Version 3.5
Creation Date 2006-08-13 01:49:22 -0600
Update Date 2013-02-08 17:12:51 -0700
HMDB ID HMDB03941
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Oxooctanoyl-CoA
Description 3-Oxooctanoyl-CoA is the substrate of the acetyl-CoA C-acyltransferase/oxoacyl-CoA thiolase A (EC 2.3.1.16, SCP2/3-oxoacyl-CoA thiolase) present in peroxisomes from normal liver. Peroxisomes beta -oxidize a wide variety of substrates including straight chain fatty acids, 2-methyl-branched fatty acids, and the side chain of the bile acid intermediates di- and trihydroxycoprostanic acids. Peroxisomes contain several beta -oxidation pathways with different substrate specificities; or example, straight chain acyl-CoAs are desaturated by palmitoyl-CoA oxidase, and their enoyl-CoAs are then converted to 3-oxoacyl-CoAs by MFP-1, which forms (hydration) and dehydrogenates L-3(3S)-hydroxyacyl-CoAs; for example, straight chain acyl-CoAs are desaturated by palmitoyl-CoA oxidase (23), and their enoyl-CoAs are then converted to 3-oxoacyl-CoAs by 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35), which forms (hydration) and dehydrogenates L-3(3S)-hydroxyacyl-CoAs and their enoyl-CoAs are then converted to the corresponding 3-oxoacyl-CoAs by long-chain-enoyl-CoA hydratase(EC 4.2.1.74), which forms and dehydrogenates D-3(3R)-hydroxyacyl-CoAs. (PMID: 9325339 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Ketooctanoyl-CoA
  2. 3-Ketooctanoyl-Coenzyme A
  3. 3-Oxooctanoyl coenzyme A
  4. 3-Oxooctanoyl-coenzyme A
  5. S-(3-Oxooctanoate
  6. S-(3-Oxooctanoate) CoA
  7. S-(3-Oxooctanoate) Coenzyme A
  8. S-(3-Oxooctanoic acid
Chemical Formula C29H48N7O18P3S
Average Molecular Weight 907.714
Monoisotopic Molecular Weight 907.198937993
IUPAC Name {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxooctanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)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-2,2-dimethyl-3-{[2-({2-[(3-oxooctanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number 54684-64-9
SMILES CCCCCC(=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/C29H48N7O18P3S/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/h15-16,18,22-24,28,40-41H,4-14H2,1-3H3,(H,31,38)(H,32,42)(H,46,47)(H,48,49)(H2,30,33,34)(H2,43,44,45)/t18-,22-,23-,24?,28-/m1/s1
InChI Key WPIVBCGRGVNDDT-FFJUWABQSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Acyl CoAs
  • Aromatic Heteropolycyclic Compounds
  • Fatty acyl CoAs(KEGG)
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Ketone
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent 3-Oxo-acyl CoAs
Ontology
Status Expected 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
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 -2.164 Not Available
Predicted Properties
Property Value Source
Water Solubility 3.07 g/L ALOGPS
LogP 0.23 ALOGPS
LogP -4.7 ChemAxon
LogS -2.47 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 380.7 A2 ChemAxon
Rotatable Bond Count 26 ChemAxon
Refractivity 200.53 ChemAxon
Polarizability 81.88 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 FDB023260
KNApSAcK ID Not Available
Chemspider ID 389506 Link_out
KEGG Compound ID C05267 Link_out
BioCyc ID 7-METHYL-3-OXOOCTANOYL-COA Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03941 Link_out
Metagene Link HMDB03941 Link_out
METLIN ID Not Available
PubChem Compound 440608 Link_out
PDB ID Not Available
ChEBI ID 28264 Link_out
References
Synthesis Reference Thorpe, Colin. A method for the preparation of 3-ketoacyl-CoA derivatives. Analytical Biochemistry (1986), 155(2), 391-4.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: 3-ketoacyl-CoA thiolase, mitochondrial
Reactions:
  • acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA [RN:R00391]
Gene Name: ACAA2
Uniprot ID: P42765 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-ketoacyl-CoA thiolase, peroxisomal
Reactions:
  • acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA [RN:R00391]
Gene Name: ACAA1
Uniprot ID: P09110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit beta, mitochondrial
Reactions:
  • acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA [RN:R00391]
Gene Name: HADHB
Uniprot ID: P55084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
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: 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
Name: Estradiol 17-beta-dehydrogenase 12
Reactions:
  • estradiol-17beta + NAD(P)+ = estrone + NAD(P)H + H+ [RN:R02352 R02353]
Gene Name: HSD17B12
Uniprot ID: Q53GQ0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA