Record Information
Version1.0
Creation date2011-09-21 00:15:26 UTC
Update date2015-07-21 06:57:15 UTC
Primary IDFDB022529
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePropionyl-CoA
DescriptionPropionyl-CoA is an intermediate in the metabolism of propanoate. Propionic aciduria is caused by an autosomal recessive disorder of propionyl coenzyme A (CoA) carboxylase deficiency (EC 6.4.1.3). In propionic aciduria, propionyl CoA accumulates within the mitochondria in massive quantities; free carnitine is then esterified, creating propionyl carnitine, which is then excreted in the urine. Because the supply of carnitine in the diet and from synthesis is limited, such patients readily develop carnitine deficiency as a result of the increased loss of acylcarnitine derivatives. This condition demands supplementation of free carnitine above the normal dietary intake to continue to remove (detoxify) the accumulating organic acids. Propionyl-CoA is a substrate for Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acetyl-coenzyme A synthetase 2-like (mitochondrial), Propionyl-CoA carboxylase alpha chain (mitochondrial), Methylmalonate-semialdehyde dehydrogenase (mitochondrial), Trifunctional enzyme beta subunit (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Malonyl-CoA decarboxylase (mitochondrial), Acetyl-coenzyme A synthetase (cytoplasmic), 3-ketoacyl-CoA thiolase (mitochondrial) and Propionyl-CoA carboxylase beta chain (mitochondrial). (PMID: 10650319) [HMDB]
CAS Number317-66-8
Structure
Thumb
Synonyms
SynonymSource
2-Methylacetyl-CoAHMDB
2-Methylacetyl-coenzyme AHMDB
alpha-Methylacetyl-CoAHMDB
alpha-Methylacetyl-coenzyme AHMDB
Propanoyl-CoAHMDB
Propanoyl-coenzyme AHMDB
Propionyl-coenzyme AHMDB
2-methylacetyl-CoAhmdb
2-methylacetyl-Coenzyme Ahmdb
alpha-methylacetyl-CoAhmdb
alpha-methylacetyl-Coenzyme Ahmdb
propanoyl-CoAhmdb
propanoyl-Coenzyme Ahmdb
Propionyl-CoAhmdb
propionyl-coenzyme Ahmdb
Predicted Properties
PropertyValueSource
Water Solubility4.27 g/LALOGPS
logP-0.31ALOGPS
logP-6.3ChemAxon
logS-2.3ALOGPS
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 Count21ChemAxon
Refractivity176.83 m³·mol⁻¹ChemAxon
Polarizability72.51 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H40N7O17P3S
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-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C24H40N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,34-35H,4-10H2,1-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13-,17-,18-,19?,23-/m1/s1
InChI KeyQAQREVBBADEHPA-UXYNFSPESA-N
Isomeric SMILESCCC(=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=C1N=CN=C2N
Average Molecular Weight823.597
Monoisotopic Molecular Weight823.141423115
Classification
Description belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1921000110-a902ba2e846c5fa3a6f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-1911000000-73f7c171e662ee7ccd1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-1910000000-e82bdc99f5bada8c440eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-9830232560-d45384d1d1a3fe0dd614JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910200000-2a67602fe8e4a74a6abeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-8900100000-d3e8a1b9393d73c218b4JSpectraViewer
ChemSpider ID388310
ChEMBL IDNot Available
KEGG Compound IDC00100
Pubchem Compound ID439164
Pubchem Substance IDNot Available
ChEBI ID15539
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01275
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33852
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPropionyl-CoA
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
Propionyl-CoA carboxylase beta chain, mitochondrialPCCBP05166
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Carnitine O-acetyltransferaseCRATP43155
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
Malonyl-CoA decarboxylase, mitochondrialMLYCDO95822
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
Acetyl-coenzyme A synthetase, cytoplasmicACSS2Q9NR19
Acetyl-coenzyme A synthetase 2-like, mitochondrialACSS1Q9NUB1
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
Propionyl-CoA carboxylase alpha chain, mitochondrialPCCAP05165
Peroxisomal trans-2-enoyl-CoA reductasePECRQ9BY49
Bile acyl-CoA synthetaseSLC27A5Q9Y2P5
Sterol O-acyltransferase 2SOAT2O75908
Acyl-CoA synthetase family member 4AASDHQ4L235
Glycerol-3-phosphate acyltransferase 1, mitochondrialGPAMQ9HCL2
Glycerol-3-phosphate acyltransferase 4AGPAT6Q86UL3
Glycerol-3-phosphate acyltransferase 2, mitochondrialGPAT2Q6NUI2
Very long-chain acyl-CoA synthetaseSLC27A2O14975
Non-specific lipid-transfer proteinSCP2P22307
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
Oxidation of Branched Chain Fatty AcidsSMP00030 Not Available
Phytanic Acid Peroxisomal OxidationSMP00450 Not Available
Propanoate MetabolismSMP00016 map00640
Threonine and 2-Oxobutanoate DegradationSMP00452 Not Available
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference