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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 14:11:32 UTC
Update Date2017-12-07 01:59:00 UTC
HMDB IDHMDB0006522
Secondary Accession Numbers
  • HMDB06522
Metabolite Identification
Common Nametrans-3-Hexenoyl-CoA
DescriptionTrans-3-hexenoyl-coa, also known as (E)-S-3-hexenoate or 3-trans-hexenoylcoenzyme a, is a member of the class of compounds known as 3-enoyl coas. 3-enoyl coas are organic compounds containing a coenzyme A substructure linked to a 3-enoyl chain. Thus, trans-3-hexenoyl-coa is considered to be a fatty ester lipid molecule. Trans-3-hexenoyl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Within the cell, trans-3-hexenoyl-coa is primarily located in the cytoplasm, in the membrane (predicted from logP) and in the mitochondria. It can also be found in the extracellular space. In the mitochondria, the enzyme 2,4-dienoyl-CoA reductase (NADPH) [EC:1.3.1.34] catalyzes the production of this metabolite from trans,trans-2,4-hexadienoyl-CoA (PMID:15629123 )..
Structure
Thumb
Synonyms
ValueSource
(e)-S-3-HexenoateHMDB
(e)-S-3-Hexenoate CoAHMDB
(e)-S-3-Hexenoate coenzyme AHMDB
(e)-S-3-Hexenoic acidHMDB
3-trans-Hexenoylcoenzyme AHMDB
S-(3E)-3-HexenoateHMDB
S-(3E)-3-Hexenoate CoAHMDB
S-(3E)-3-Hexenoate coenzyme AHMDB
S-(3E)-3-Hexenoic acidHMDB
Chemical FormulaC27H44N7O17P3S
Average Molecular Weight863.661
Monoisotopic Molecular Weight863.172723243
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(3E)-hex-3-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(3E)-hex-3-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number6599-65-1
SMILES
CC\C=C\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/C27H44N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h5-6,14-16,20-22,26,37-38H,4,7-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/b6-5+/t16-,20-,21-,22?,26-/m1/s1
InChI KeySKDDJNFRAZIJIG-PFNGVMQSSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 3-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 3-enoyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-enoyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility3.63 g/LALOGPS
logP0.2ALOGPS
logP-5.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity191.75 m³·mol⁻¹ChemAxon
Polarizability77.43 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-2901000120-b45e54c731e8766bdc8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913000000-7d0c974ecf8a037ef681View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1901000000-9d37e047b82195621966View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01sj-7930140450-6d6fccf18ea12ce4373cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6910010000-d785e36ebf23b0627039View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-6eea26f271d7f30bc840View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationNot 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
FoodDB IDFDB023957
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477848
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yu W, Chu X, Chen G, Li D: Studies of human mitochondrial 2,4-dienoyl-CoA reductase. Arch Biochem Biophys. 2005 Feb 1;434(1):195-200. [PubMed:15629123 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Auxiliary enzyme of beta-oxidation. It participates in the metabolism of unsaturated fatty enoyl-CoA esters having double bonds in both even- and odd-numbered positions. Catalyzes the NADP-dependent reduction of 2,4-dienoyl-CoA to yield trans-3-enoyl-CoA.
Gene Name:
DECR1
Uniprot ID:
Q16698
Molecular weight:
36067.4