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Record Information
Version3.6
Creation Date2007-05-23 05:35:22 UTC
Update Date2016-02-11 01:07:30 UTC
HMDB IDHMDB06402
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Oxohexadecanoyl-CoA
Description3-Oxohexadecanoyl-CoA has a role in the synthesis and oxidation of fatty acid. It is involved in the pathway, fatty acid elongation in mitochondria. In this pathway Acetyl-CoA is acted upon by the enzyme, acetyl-CoA C-acyltransferase to produce 3-Oxohexadecanoyl-CoA. 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 the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group it is usually referred to as 'CoASH' or 'HSCoA'.
Structure
Thumb
Synonyms
ValueSource
3-Ketopalmitoleoyl-CoAHMDB
3-Ketopalmitoleoyl-coenzyme AHMDB
3-Ketopalmitoyl-CoAHMDB
3-Ketopalmitoyl-coenzyme AHMDB
3-oxo-cis-9-Hexadecenoyl-CoAHMDB
3-oxo-cis-9-Hexadecenoyl-coenzyme AHMDB
3-Oxohexadec-9Z-enoyl-CoAHMDB
3-Oxohexadec-9Z-enoyl-coenzyme AHMDB
3-Oxohexadec-cis-9-enoyl-CoAHMDB
3-Oxohexadec-cis-9-enoyl-coenzyme AHMDB
3-Oxopalmitoleoyl-CoAHMDB
3-Oxopalmitoleoyl-coenzyme AHMDB
3-Oxopalmitoyl-CoAHMDB
3-Oxopalmitoyl-coenzyme AHMDB
Chemical FormulaC37H64N7O18P3S
Average Molecular Weight1019.926
Monoisotopic Molecular Weight1019.324138505
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-oxohexadecanoyl)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-oxohexadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number34619-89-1
SMILES
CCCCCCCCCCCCCC(=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/C37H64N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-24,26,30-32,36,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t26-,30-,31-,32?,36-/m1/s1
InChI KeyInChIKey=NQMPLXPCRJOSHL-TZIIWEFPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain 3-oxoacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Ketone
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but 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
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.01 mg/mLALOGPS
logP1.96ALOGPS
logP-1.2ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 Å2ChemAxon
Rotatable Bond Count34ChemAxon
Refractivity237.34 m3·mol-1ChemAxon
Polarizability99.31 Å3ChemAxon
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-4902010200-41e4cf6d39eaf589148eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913030000-3702c3a476f36f032656View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000100-43ec495f5ad7705f76ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kyi-9681231300-516949aaf17232c14bfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4931200000-62f23b99716fb50af5edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-442610dbd007f0499935View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Peroxisome
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Carnitine palmitoyl transferase deficiency (I)SMP00538Not Available
Carnitine palmitoyl transferase deficiency (II)SMP00541Not Available
Ethylmalonic EncephalopathySMP00181Not Available
Fatty Acid Elongation In MitochondriaSMP00054map00062
Fatty acid MetabolismSMP00051map00071
Glutaric Aciduria Type ISMP00185Not Available
Long chain acyl-CoA dehydrogenase deficiency (LCAD)SMP00539Not Available
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)SMP00544Not Available
Medium chain acyl-coa dehydrogenase deficiency (MCAD)SMP00542Not Available
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482Not Available
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)SMP00235Not Available
Trifunctional protein deficiencySMP00545Not Available
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)SMP00540Not 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 IDFDB023908
KNApSAcK IDNot Available
Chemspider ID389499
KEGG Compound IDC05259
BioCyc ID3-OXOPALMITOYL-COA
BiGG ID45445
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06402
Metagene LinkHMDB06402
METLIN IDNot Available
PubChem Compound440601
PDB IDNot Available
ChEBI ID15491
References
Synthesis ReferenceNot Available
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
Tetradecanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxohexadecanoyl-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
Tetradecanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxohexadecanoyl-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
Tetradecanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxohexadecanoyl-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-Hydroxyhexadecanoyl-CoA + NAD → 3-Oxohexadecanoyl-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-Hydroxyhexadecanoyl-CoA + NAD → 3-Oxohexadecanoyl-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-Hydroxyhexadecanoyl-CoA + NAD → 3-Oxohexadecanoyl-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
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of estrone (E1) into estradiol (E2), suggesting a central role in estrogen formation. Its strong expression in ovary and mammary gland suggest that it may constitute the major enzyme responsible for the conversion of E1 to E2 in women. Also has 3-ketoacyl-CoA reductase activity, reducing both long chain 3-ketoacyl-CoAs and long chain fatty acyl-CoAs, suggesting a role in long fatty acid elongation.
Gene Name:
HSD17B12
Uniprot ID:
Q53GQ0
Molecular weight:
34323.875