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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:58:04 UTC
Update Date2021-09-14 15:17:51 UTC
HMDB IDHMDB0060378
Secondary Accession Numbers
  • HMDB60378
Metabolite Identification
Common Name3-Oxoadipyl-CoA
Description3-Oxoadipyl-CoA, also known as b-ketoadipyl-CoA, belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative. Thus, 3-oxoadipyl-CoA is considered to be a fatty ester lipid molecule. 3-Oxoadipyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866052
Synonyms
ValueSource
beta-Ketoadipyl-CoAChEBI
S-(5-Carboxy-3-oxopentanoyl)-coenzyme AChEBI
b-Ketoadipyl-CoAGenerator
Β-ketoadipyl-CoAGenerator
Chemical FormulaC27H42N7O20P3S
Average Molecular Weight909.644
Monoisotopic Molecular Weight909.141817045
IUPAC Name6-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4,6-dioxohexanoic acid
Traditional Name6-({2-[(3-{[(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4,6-dioxohexanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC(=O)CCC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
InChI Identifier
InChI=1S/C27H42N7O20P3S/c1-27(2,22(41)25(42)30-6-5-16(36)29-7-8-58-18(39)9-14(35)3-4-17(37)38)11-51-57(48,49)54-56(46,47)50-10-15-21(53-55(43,44)45)20(40)26(52-15)34-13-33-19-23(28)31-12-32-24(19)34/h12-13,15,20-22,26,40-41H,3-11H2,1-2H3,(H,29,36)(H,30,42)(H,37,38)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t15-,20-,21-,22+,26-/m1/s1
InChI KeyVKKKAAPGXHWXOO-BIEWRJSYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-oxo-acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Medium-chain keto acid
  • Purine
  • Gamma-keto acid
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Hydroxy fatty acid
  • Thia fatty acid
  • Imidolactam
  • Fatty amide
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Keto acid
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Ketone
  • Thiocarboxylic acid ester
  • Organoheterocyclic compound
  • Thiocarboxylic acid or derivatives
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Sulfenyl compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organosulfur compound
  • Primary amine
  • Amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.68 g/LALOGPS
logP10(-0.31) g/LALOGPS
logP10(-4.2) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.83ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area424.98 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity194.04 m³·mol⁻¹ChemAxon
Polarizability79.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 10V, Positive-QTOFsplash10-000i-1891000240-c524c3ff5fd842d57ece2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 20V, Positive-QTOFsplash10-000i-0971100000-80d5547f65c1fc8150de2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 40V, Positive-QTOFsplash10-000i-2950000000-612b6d4425f697b409932015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 10V, Negative-QTOFsplash10-05nf-3910031342-e4c44893eb8c508e6f422015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 20V, Negative-QTOFsplash10-001i-3910110010-0f13889f40f293baf8912015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 40V, Negative-QTOFsplash10-057i-6900100000-b08ba94bf6810bae77112015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 10V, Positive-QTOFsplash10-006x-0000000191-b8c40f2f26e5fcde41c92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 20V, Positive-QTOFsplash10-00di-2000100190-001f90d2b3594f2760732021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 40V, Positive-QTOFsplash10-0udi-1112900100-53b42ae4a8ec6933f5312021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 10V, Negative-QTOFsplash10-0a4i-0000000079-6cb5fca35d6adce63b632021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 20V, Negative-QTOFsplash10-00tf-6000003972-4ec89f8fd41c03afc96a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipyl-CoA 40V, Negative-QTOFsplash10-002b-9100200120-6e901dc655646da8536a2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7822126
KEGG Compound IDC02232
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543153
PDB IDNot Available
ChEBI ID15490
Food Biomarker OntologyNot Available
VMH IDOXADPCOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
ACAA2
Uniprot ID:
P42765
Molecular weight:
41923.82
Reactions
Succinyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxoadipyl-CoAdetails
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
Reactions
Succinyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxoadipyl-CoAdetails
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
HADHB
Uniprot ID:
P55084
Molecular weight:
51293.955
Reactions
Succinyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxoadipyl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
(3S)-3-Hydroxyadipyl-CoA + NAD → 3-Oxoadipyl-CoA + NADH + Hydrogen Iondetails
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
(3S)-3-Hydroxyadipyl-CoA + NAD → 3-Oxoadipyl-CoA + NADH + Hydrogen Iondetails