| Common Name |
trans-3-Decenoyl-CoA
| Description |
trans-3-Decenoyl-CoA is an intermediate in fatty acid metabolism. trans-3-Decenoyl-CoA is the substrate of medium-chain acyl-CoA dehydrogenase (MCAD, EC 1.3.99.3) MCAD acts on C4-C16 acyl-CoAs with its peak activity toward medium-chain (C6-C12) substrates. MCAD is a key enzyme for the beta-oxidation of fatty acids. MCAD deficiency is caused by mutation in the medium-chain acyl-CoA dehydrogenase gene (ACADM; OMIM 607008 ). Inherited deficiency of medium-chain acyl-CoA dehydrogenase is characterized by intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels. The disorder may be severe, and even fatal, in young patients. It has been reported that between 19 and 25% of patients with undiagnosed deficiency of MCAD die during their first episode of metabolic decompensation. (PMID: 15850406 ).
| Structure |
| Synonyms |
| Value |
Source |
3-trans-Decenoyl-CoAChEBI
3-trans-Decenoyl-coenzyme AChEBI
trans-3-Decenoyl-coenzyme AChEBI
trans-Dec-3-enoyl-coenzyme AChEBI
(e)-S-3-DecenoateHMDB
(e)-S-3-Decenoate CoAHMDB
(e)-S-3-Decenoate coenzyme AHMDB
(e)-S-3-Decenoic acidHMDB
S-(3E)-3-DecenoateHMDB
S-(3E)-3-DecenoateCoAHMDB
S-(3E)-3-Decenoatecoenzyme AHMDB
S-(3E)-3-Decenoic acidHMDB
| Chemical Formlia |
C31H52N7O17P3S
| Average Molecliar Weight |
919.768
| Monoisotopic Molecliar Weight |
919.235323499
| IUPAC Name |
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(3E)-dec-3-enoylslifanyl]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 |
3-trans-decenoyl-coa
| CAS Registry Number |
6410-54-4
| SMILES |
CCCCCCC=CCC(=O)SCCNC(=O)CCNC(=O)[C@H](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/C31H52N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h9-10,18-20,24-26,30,41-42H,4-8,11-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b10-9+/t20-,24-,25-,26+,30-/m1/s1
| InChI Key |
CQGVNMQHZQJNII-ZJZQAHHTSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as 3-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 3-enoyl chain.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Fatty Acyls
| Direct Parent |
3-enoyl CoAs
| Alternative Parents |
Acyl CoAs
Coenzyme A and derivatives
Purine ribonucleoside diphosphates
Pentose phosphates
Ribonucleoside 3-phosphates
Beta amino acids and derivatives
Glycosylamines
6-aminopurines
Organic pyrophosphates
Monosaccharide phosphates
Aminopyrimidines and derivatives
Monoalkyl phosphates
Primary aromatic amines
N-substituted imidazoles
N-acyl amines
Imidolactams
Oxolanes
Heteroaromatic compounds
Secondary alcohols
Thioesters
Secondary carboxylic acid amides
Carbothioic S-esters
Azacyclic compounds
Oxacyclic compounds
Slifenyl compounds
Carbonyl compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
| 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
Monosaccharide phosphate
Organic pyrophosphate
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Fatty amide
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Primary aromatic amine
Pyrimidine
Oxolane
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Thiocarboxylic acid ester
Carboxamide group
Carbothioic s-ester
Secondary carboxylic acid amide
Secondary alcohol
Slifenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Amine
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organoslifur compound
Organic oxygen compound
Organopnictogen compound
Primary amine
Organic oxide
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
medium-chain fatty acyl-CoA (CHEBI:29126 )
trans-3-enoyl-CoA (CHEBI:29126 )
| Ontology |
| Status |
Expected 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 Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility2.76 mg/mLALOGPS
logP0.99ALOGPS
logP-3.5ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 Å2ChemAxon
Rotatable Bond Count27ChemAxon
Refractivity210.16 m3·mol-1ChemAxon
Polarizability85.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022862
| KNApSAcK ID |
Not Available
| Chemspider ID |
13148715
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02137
| Metagene Link |
HMDB02137
| METLIN ID |
6504
| PubChem Compound |
16019966
| PDB ID |
Not Available
| ChEBI ID |
29126
Product: CARM1-IN-1 (hydrochloride)
References |
| Synthesis Reference |
Kunau, W. H.; Dommes, V.; Dommes, P. Degradation of unsaturated fatty acids. 4-Enoyl-CoA reductase: purification, characterization and physiological function. Progress in Lipid Research (1981), 20(1-4), 327-30. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Tserng KY, Jin SJ: NADPH-dependent reductive metabolism of cis-5 unsaturated fatty acids. A revised pathway for the beta-oxidation of oleic acid. J Biol Chem. 1991 Jun 25;266(18):11614-20. [PubMed:2050669 ]
- Zeng J, Li D: Intrinsic isomerase activity of medium-chain acyl-CoA dehydrogenase. Biochemistry. 2005 May 3;44(17):6715-22. [PubMed:15850406 ]
|
Enzymes
- General function:
- Involved in acyl-CoA dehydrogenase activity
- Specific function:
- This enzyme is specific for acyl chain lengths of 4 to 16.
- Gene Name:
- ACADM
- Uniprot ID:
- P11310
- Molecular weight:
- 46587.98
PMID: 16025138