| Common Name |
4-cis-Decenoyl-CoA
| Description |
cis-4-Decenoyl-CoA is an intermediate of linoleic acid catabolism, degraded by a mitochondrial 4-enoyl-CoA reductase. (PMID: 729581 ). There are two 2,4-dienoyl-CoA reductases (formerly called 4-enoyl-CoA reductase) in liver, one in mitochondria and another one in peroxisomes. Isolated peroxisomes metabolize 4-cis-decenoyl-CoA via the 2,4-dienoyl-CoA reductase pathway. (PMID: 7263650 ).
| Structure |
| Synonyms |
| Value |
Source |
4Z-Decaenoyl-CoAHMDB
4Z-Decaenoyl-coenzyme AHMDB
cis-Deca-4-enoyl-CoAHMDB
cis-Deca-4-enoyl-coenzime aHMDB
cis-Deca-4-enoyl-coenzyme AHMDB
Deca-4Z-enoyl-CoAHMDB
Deca-4Z-enoyl-coenzyme AHMDB
4-Decenoyl-coenzyme AMeSH
cis-4-Decenoyl-CoAMeSH
cis-4-Decenoyl-coenzyme AMeSH
| 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-[(4E)-dec-4-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 |
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-{[2-({2-[(4E)-dec-4-enoylslifanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid
| CAS Registry Number |
69281-30-7
| SMILES |
CCCCCC=CCCC(=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/h8-9,18-20,24-26,30,41-42H,4-7,10-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b9-8+/t20-,24-,25-,26+,30-/m1/s1
| InChI Key |
QTOYQSMKQWCWOX-CCVVLBLYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as medium-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a medium aliphatic chain of 6 to 12 carbon atoms.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Fatty Acyls
| Direct Parent |
Medium-chain fatty acyl CoAs
| Alternative Parents |
Coenzyme A and derivatives
Purine ribonucleoside diphosphates
Ribonucleoside 3-phosphates
Pentose phosphates
Beta amino acids and derivatives
Glycosylamines
6-aminopurines
Monosaccharide phosphates
Organic pyrophosphates
Aminopyrimidines and derivatives
Monoalkyl phosphates
Primary aromatic amines
Imidolactams
N-acyl amines
N-substituted imidazoles
Oxolanes
Heteroaromatic compounds
Thioesters
Secondary alcohols
Carbothioic S-esters
Secondary carboxylic acid amides
Oxacyclic compounds
Slifenyl compounds
Azacyclic compounds
Hydrocarbon derivatives
Carbonyl compounds
Organic oxides
Organopnictogen compounds
| 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 |
Not Available
| 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 Solubility2.79 mg/mLALOGPS
logP0.96ALOGPS
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
Polarizability86.61 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 |
FDB022867
| KNApSAcK ID |
Not Available
| Chemspider ID |
4947585
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02145
| Metagene Link |
HMDB02145
| METLIN ID |
6509
| PubChem Compound |
6443609
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: BG45
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Chen Q, Luthria DL, Sprecher H: Analysis of the acyl-CoAs that accumulate during the peroxisomal beta-oxidation of arachidonic acid and 6,9,12-octadecatrienoic acid. Arch Biochem Biophys. 1998 Jan 15;349(2):371-5. [PubMed:9448727 ]
- Kunau WH, Dommes P: Degradation of unsaturated fatty acids. Identification of intermediates in the degradation of cis-4-decenoly-CoA by extracts of beef-liver mitochondria. Eur J Biochem. 1978 Nov 15;91(2):533-44. [PubMed:729581 ]
- Dommes V, Baumgart C, Kunau WH: Degradation of unsaturated fatty acids in peroxisomes. Existence of a 2,4-dienoyl-CoA reductase pathway. J Biol Chem. 1981 Aug 25;256(16):8259-62. [PubMed:7263650 ]
- (). Engeland K, Kindl H. Evidence for a peroxisomal fatty acid beta-oxidation involving D-3-hydroxyacyl-CoAs. Characterization of two forms of hydro-lyase that convert D-(-)-3-hydroxyacyl-CoA into 2-trans-enoyl-CoA. Eur J Biochem. 1991 Aug 15;200(1):171-8.. .
- (). Horst Schulz, Wolf-H. Kunau. Beta-oxidation of unsaturated fatty acids: a revised pathway. Pages 403-406. . .
|
PMID: 15266010