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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:46:24 UTC
Update Date2017-12-07 01:52:49 UTC
HMDB IDHMDB0003937
Secondary Accession Numbers
  • HMDB03937
  • HMDB06350
Metabolite Identification
Common Name3-Oxododecanoyl-CoA
Description3-Oxododecanoyl-CoA is a human metabolite involved in the fatty acid elongation in mitochondria pathway. The enzyme acetyl-CoA C-acyltransferase catalyzes the formation of this metabolite from Acetyl-CoA.
Structure
Thumb
Synonyms
ValueSource
3-Oxododecanoyl-coenzyme AHMDB
3-Oxolauroyl-CoAHMDB
Chemical FormulaC33H56N7O18P3S
Average Molecular Weight963.82
Monoisotopic Molecular Weight963.261538249
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-oxododecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxododecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number78303-19-2
SMILES
CCCCCCCCCC(=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/C33H56N7O18P3S/c1-4-5-6-7-8-9-10-11-21(41)16-24(43)62-15-14-35-23(42)12-13-36-31(46)28(45)33(2,3)18-55-61(52,53)58-60(50,51)54-17-22-27(57-59(47,48)49)26(44)32(56-22)40-20-39-25-29(34)37-19-38-30(25)40/h19-20,22,26-28,32,44-45H,4-18H2,1-3H3,(H,35,42)(H,36,46)(H,50,51)(H,52,53)(H2,34,37,38)(H2,47,48,49)/t22-,26-,27-,28?,32-/m1/s1
InChI KeyHQANBZHVWIDNQZ-IIZVUBDFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
  • Pentose monosaccharide
  • Organic pyrophosphate
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • Pyrimidine
  • 1,3-dicarbonyl compound
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Primary aromatic amine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Oxolane
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Thiocarboxylic acid ester
  • Ketone
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Biochemical process:

    Chemical reaction:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.364Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.82 g/LALOGPS
logP0.98ALOGPS
logP-2.9ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity218.94 m³·mol⁻¹ChemAxon
Polarizability89.72 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1911101102-28c1a77e39e689b9d6ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920300000-fe0fcd490fad648c21fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900001000-b14c48fd7f94587c46c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02cs-2921121203-f382e032b417ee8f5e34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2910100001-796e51294930a7b17077View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-cd1cef9797873819f254View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Carnitine palmitoyl transferase deficiency (I)Pw000514Pw000514 greyscalePw000514 simpleNot Available
Carnitine palmitoyl transferase deficiency (II)Pw000517Pw000517 greyscalePw000517 simpleNot Available
Ethylmalonic EncephalopathyPw000106Pw000106 greyscalePw000106 simpleNot Available
Fatty Acid Elongation In MitochondriaPw000022Pw000022 greyscalePw000022 simpleMap00062
Fatty Acid MetabolismPw000023Pw000023 greyscalePw000023 simpleMap00071
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 IDFDB023256
KNApSAcK IDNot Available
Chemspider ID389502
KEGG Compound IDC05263
BioCyc IDNot Available
BiGG ID45453
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440604
PDB IDNot Available
ChEBI ID27868
References
Synthesis ReferenceKrahling, Jeffrey B.; Tolbert, N. E. Peroxisomal b-ketothiolase. Archives of Biochemistry and Biophysics (1981), 209(1), 100-10. CODEN: ABBIA4 ISSN:0003-9861. CAN 95:37869 AN 1981:437869
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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
Decanoyl-CoA (n-C10:0CoA) + Acetyl-CoA → Coenzyme A + 3-Oxododecanoyl-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
Decanoyl-CoA (n-C10:0CoA) + Acetyl-CoA → Coenzyme A + 3-Oxododecanoyl-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
Decanoyl-CoA (n-C10:0CoA) + Acetyl-CoA → Coenzyme A + 3-Oxododecanoyl-CoAdetails
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)-3-Hydroxydodecanoyl-CoA + NAD → 3-Oxododecanoyl-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
(S)-3-Hydroxydodecanoyl-CoA + NAD → 3-Oxododecanoyl-CoA + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
(S)-3-Hydroxydodecanoyl-CoA + NAD → 3-Oxododecanoyl-CoA + NADH + Hydrogen Iondetails
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