Record Information
Version2.0
Creation Date2012-05-31 14:08:40 -0600
Update Date2015-06-03 15:54:52 -0600
Secondary Accession Numbers
  • ECMDB06503
Identification
Name:Phenylacetyl-CoA
Description:Phenylacetyl-CoA is an intermediate in the metabolism of phenylacetic acid. Phenylacetyl-CoA is synthesized by the Phenylacetyl-CoA ligase protein paaK using the following reaction: ATP + phenylacetate + CoA = AMP + diphosphate + phenylacetyl-CoA.
Structure
Thumb
Synonyms:
  • Phenylacetate-CoA
  • Phenylacetic acid-CoA
Chemical Formula:C29H42N7O17P3S
Weight:Average: 885.667
Monoisotopic: 885.157073179
InChI Key:ZIGIFDRJFZYEEQ-CECATXLMSA-N
InChI:InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24+,28-/m1/s1
CAS number:7532-39-0
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-phenylacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name:phenylacetyl-coa
SMILES:CC(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)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC1=CC=CC=C1
Chemical Taxonomy
DescriptionThis compound 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
  • Alkyl phosphate
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Benzenoid
  • Fatty amide
  • Phosphoric acid ester
  • Monocyclic benzene moiety
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.19 g/LALOGPS
logP-0.03ALOGPS
logP-5.1ChemAxon
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 Count22ChemAxon
Refractivity196.93 m³·mol⁻¹ChemAxon
Polarizability79.56 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylethylamine metabolismPW002027 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Phenylalanine metabolism ec00360
EcoCyc Pathways:
  • phenylacetate degradation I (aerobic) PWY0-321
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1902000120-2675b76ad9f54835a9caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0912000000-529bf6f64f6aacd6d751View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-620185a5c119150569f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-3911030340-ecb4e904f2d54efd9472View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-3900010010-92262d3c897c5a9b8604View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-467f72db3de4e82f7bbeView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Potempska A, Loo YH, Wisniewski HM: On the possible mechanism of phenylacetate neurotoxicity: inhibition of choline acetyltransferase by phenylacetyl-CoA. J Neurochem. 1984 May;42(5):1499-501. Pubmed: 6142928
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15537
HMDB IDHMDB06503
Pubchem Compound ID439267
Kegg IDC00582
ChemSpider ID145148
Wikipedia IDNot Available
BioCyc IDCPD-207
EcoCyc IDCPD-207
Ligand ExpoFAQ

Enzymes

General function:
Involved in electron carrier activity
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaE
Uniprot ID:
P76081
Molecular weight:
39320
General function:
Involved in catalytic activity
Specific function:
Catalyzes the activation of phenylacetic acid to phenylacetyl-CoA
Gene Name:
paaK
Uniprot ID:
P76085
Molecular weight:
48953
Reactions
ATP + phenylacetate + CoA = AMP + diphosphate + phenylacetyl-CoA.
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaB
Uniprot ID:
P76078
Molecular weight:
10942
General function:
Involved in oxidoreductase activity
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaA
Uniprot ID:
P76077
Molecular weight:
35499
Reactions
Phenylacetyl-CoA + NADPH + O(2) = 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP(+) + H(2)O.
General function:
Not Available
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaD
Uniprot ID:
P76080
Molecular weight:
18324
General function:
Involved in oxidoreductase activity
Specific function:
May be part of a multicomponent oxygenase involved in phenylacetyl-CoA hydroxylation
Gene Name:
paaC
Uniprot ID:
P76079
Molecular weight:
27877
General function:
Not Available
Specific function:
Not Available
Gene Name:
paaI
Uniprot ID:
P76084
Molecular weight:
Not Available