Record Information
Version1.0
Creation date2011-09-21 00:27:11 UTC
Update date2015-07-21 06:57:36 UTC
Primary IDFDB023267
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDecenoyl-CoA
Description(2E)-Decenoyl-CoA is a beta-oxidation intermediate, the substrate of the enzyme peroxisomal acyl-CoA thioesterase 2 (PTE-2, 3.1.2.2), which is localized in the peroxisome. The peroxisomal beta-oxidation system contains two sets of enzymes, one of which is involved in the oxidation of branched chain fatty acids and intermediates in the hepatic bile acid biosynthetic pathway and consists of one or two branched-chain acyl-CoA oxidase(s), a D-specific bifunctional protein and the sterol carrier-like protein x (SCPx). Peroxisomes are cellular organelles present in all eukaryotic cells. They play an indispensable role in the metabolism of a variety of lipids including very long-chain fatty acids, dicarboxylic fatty acids, bile acids, prostaglandins, leukotrienes, thromboxanes, pristanic acid, and xenobiotic fatty acids. (PMID: 11673457) [HMDB]
CAS Number10018-95-8
Structure
Thumb
Synonyms
SynonymSource
(e)-S-2-DecenoateHMDB
(e)-S-2-Decenoate CoAHMDB
(e)-S-2-Decenoate coenzyme AHMDB
(e)-S-2-Decenoic acidHMDB
2-trans-Decenoyl-CoAHMDB
2-trans-Decenoyl-coenzyme AHMDB
S-(2E)-2-DecenoateHMDB
S-(2E)-2-Decenoate CoAHMDB
S-(2E)-2-Decenoate coenzyme AHMDB
S-(2E)-2-Decenoic acidHMDB
trans-2-Decenoylcoenzyme AHMDB
trans-D2,3-Decenoyl-CoAHMDB
trans-D2,3-Decenoyl-coenzyme AHMDB
trans-Dec-2-enoyl-CoAHMDB
trans-Dec-2-enoyl-coenzyme AHMDB
(E)-S-2-decenoatehmdb
(E)-S-2-decenoate CoAhmdb
(E)-S-2-decenoate Coenzyme Ahmdb
(E)-S-2-decenoic acidhmdb
2-trans-Decenoyl-Coenzyme Ahmdb
Decenoyl-CoAmanual
S-(2E)-2-decenoatehmdb
S-(2E)-2-decenoate CoAhmdb
S-(2E)-2-decenoate Coenzyme Ahmdb
S-(2E)-2-decenoic acidhmdb
trans-D2,3-Decenoyl-Coenzyme Ahmdb
trans-Dec-2-enoyl-Coenzyme Ahmdb
Predicted Properties
PropertyValueSource
Water Solubility2.71 g/LALOGPS
logP0.92ALOGPS
logP-2.9ChemAxon
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 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity210.14 m³·mol⁻¹ChemAxon
Polarizability87.08 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC31H52N7O17P3S
IUPAC name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E)-dec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
InChI IdentifierInChI=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/h10-11,18-20,24-26,30,41-42H,4-9,12-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b11-10+/t20-,24-,25-,26?,30-/m1/s1
InChI KeyMGNBGCRQQFMNBM-VHTAIFHGSA-N
Isomeric SMILESCCCCCCC\C=C\C(=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
Average Molecular Weight919.768
Monoisotopic Molecular Weight919.235323499
Classification
Description belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentMedium-chain 2-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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1911101102-d7c5b2f21ab6de6c61a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0940200000-818ed4496f38cd7d6a74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910001000-c714a78ef8b78dd3a10aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0lgi-2911030303-9132d7ddb990defb4306View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-2910010000-1700c7e9cc7f78c834b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-20950b9a12bc4a9a836cView in MoNA
ChemSpider ID4444334
ChEMBL IDNot Available
KEGG Compound IDC05275
Pubchem Compound ID5280768
Pubchem Substance IDNot Available
ChEBI ID10723
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03948
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Hepatic triacylglycerol lipaseLIPCP11150
Diacylglycerol O-acyltransferase 1DGAT1O75907
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Diacylglycerol O-acyltransferase 2DGAT2Q96PD7
2-acylglycerol O-acyltransferase 1MOGAT1Q96PD6
2-acylglycerol O-acyltransferase 3MOGAT3Q86VF5
Glycerol-3-phosphate acyltransferase 3AGPAT9Q53EU6
Fatty acyl-CoA reductase 2FAR2Q96K12
Acyl-CoA wax alcohol acyltransferase 2AWAT2Q6E213
Sterol O-acyltransferase 1SOAT1P35610
Peroxisome proliferator-activated receptor gammaPPARGP37231
Long-chain fatty acid transport protein 3SLC27A3Q5K4L6
Long-chain fatty acid transport protein 4SLC27A4Q6P1M0
Fatty acyl-CoA reductase 1FAR1Q8WVX9
Acyl-CoA wax alcohol acyltransferase 1AWAT1Q58HT5
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Diacylglycerol O-acyltransferase 2-like protein 6DGAT2L6Q6ZPD8
Putative diacylglycerol O-acyltransferase 2-like protein 7DGAT2L7Q6IED9
Acyl-CoA-binding proteinDBIP07108
Peroxisome proliferator-activated receptor deltaPPARDQ03181
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHBP21953
Cytosolic acyl coenzyme A thioester hydrolase-likeACOT7LQ6ZUV0
Long-chain-fatty-acid--CoA ligase ACSBG2ACSBG2Q5FVE4
Long-chain-fatty-acid--CoA ligase ACSBG1ACSBG1Q96GR2
3-ketoacyl-CoA thiolase, mitochondrialACAA2P42765
Peroxisomal trans-2-enoyl-CoA reductasePECRQ9BY49
Bile acyl-CoA synthetaseSLC27A5Q9Y2P5
Sterol O-acyltransferase 2SOAT2O75908
Acyl-CoA synthetase family member 4AASDHQ4L235
Enoyl-CoA hydratase, mitochondrialECHS1P30084
Glycerol-3-phosphate acyltransferase 1, mitochondrialGPAMQ9HCL2
Glycerol-3-phosphate acyltransferase 4AGPAT6Q86UL3
Glycerol-3-phosphate acyltransferase 2, mitochondrialGPAT2Q6NUI2
Very long-chain acyl-CoA synthetaseSLC27A2O14975
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
1-acyl-sn-glycerol-3-phosphate acyltransferase gammaAGPAT3Q9NRZ7
1-acyl-sn-glycerol-3-phosphate acyltransferase betaAGPAT2O15120
1-acyl-sn-glycerol-3-phosphate acyltransferase alphaAGPAT1Q99943
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilonAGPAT5Q9NUQ2
1-acyl-sn-glycerol-3-phosphate acyltransferase deltaAGPAT4Q9NRZ5
Lysocardiolipin acyltransferase 1LCLAT1Q6UWP7
Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrialDBTP11182
3-ketoacyl-CoA thiolase, peroxisomalACAA1P09110
Trifunctional enzyme subunit beta, mitochondrialHADHBP55084
Dihydroxyacetone phosphate acyltransferaseGNPATO15228
Peroxisome proliferator-activated receptor alphaPPARAQ07869
Fatty acid-binding protein, heartFABP3P05413
Acyl-CoA dehydrogenase family member 10ACAD10Q6JQN1
Acyl-CoA dehydrogenase family member 11ACAD11Q709F0
Lysophospholipid acyltransferase LPCAT4LPCAT4Q643R3
Enoyl-CoA delta isomerase 2, mitochondrialECI2O75521
Nef-associated protein 1C9orf156Q9BU70
Acyl-coenzyme A thioesterase 9, mitochondrialACOT9Q9Y305
Acyl-CoA synthetase family member 3, mitochondrialACSF3Q4G176
Acyl-CoA synthetase family member 2, mitochondrialACSF2Q96CM8
Acyl-coenzyme A thioesterase 11ACOT11Q8WXI4
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid Elongation In MitochondriaSMP00054 map00062
Fatty acid MetabolismSMP00051 map00071
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference