ECMDB: Phenylacetyl-CoA (ECMDB06503) (M2MDB000676)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (7)XML

Proteins (975)

Record Information

Version

2.0

Creation Date

2012-05-31 14:08:40 -0600

Update Date

2015-06-03 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

MOL SDF PDB SMILES InChI

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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

acyl-CoA (CHEBI:15537 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	3.19 g/L	ALOGPS
logP	-0.03	ALOGPS
logP	-5.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	196.93 m³·mol⁻¹	ChemAxon
Polarizability	79.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Hydrogen ion + NADPH + Oxygen + Phenylacetyl-CoA > Water + NADP + Ring 1,2-epoxyphenylacetyl-CoA
Adenosine triphosphate + Coenzyme A + Benzeneacetic acid <> Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate
Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion <> 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
Phenylacetyl-CoA + Water <> Benzeneacetic acid + Coenzyme A
Coenzyme A + phenylacetate + Adenosine triphosphate > Phenylacetyl-CoA + Pyrophosphate + Adenosine monophosphate
Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion > 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water
Phenylacetyl-CoA + NADPH + Oxygen > 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water
Adenosine triphosphate + Benzeneacetic acid + CoA > Adenosine monophosphate + Pyrophosphate + Phenylacetyl-CoA
Benzeneacetic acid + Adenosine triphosphate + Coenzyme A > Adenosine monophosphate + Pyrophosphate + Phenylacetyl-CoA
Phenylacetyl-CoA + Hydrogen ion + NADPH + Oxygen > Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA

SMPDB Pathways:

Phenylalanine metabolism	PW000921
Phenylethylamine metabolism	PW002027

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 Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1902000120-2675b76ad9f54835a9ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0912000000-529bf6f64f6aacd6d751	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-620185a5c119150569f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-3911030340-ecb4e904f2d54efd9472	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00o0-3900010010-92262d3c897c5a9b8604	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-467f72db3de4e82f7bbe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000090-773f38ddd970a96002b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-017i-5100100390-5d328a7aaed3dcc1dfa6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002r-9002320720-f91bf300c731f9f42e04	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000090-c7825ec5d50f1cbcc9b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00p0-1204300290-163a53f40212d6e050c1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0109000000-f82ff9edb826d50c5d35	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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

Links

External Links:

Resource	Link
CHEBI ID	15537
HMDB ID	HMDB06503
Pubchem Compound ID	439267
Kegg ID	C00582
ChemSpider ID	145148
Wikipedia ID	Phenylacetyl-CoA
BioCyc ID	CPD-207
EcoCyc ID	CPD-207
Ligand Expo	FAQ

Enzymes

Protein Details

1. Probable phenylacetic acid degradation NADH oxidoreductase paaE

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

Protein Details

2. Phenylacetate-coenzyme A ligase

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.

Protein Details

3. Phenylacetic acid degradation protein paaB

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

Protein Details

4. Phenylacetic acid degradation protein paaA

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.

Protein Details

5. Phenylacetic acid degradation protein paaD

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

Protein Details

6. Phenylacetic acid degradation protein paaC

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

Protein Details

7. thioesterase, most active with ring-hydroxylated phenylacetyl-coenzyme A thioesters

General function:: Not Available
Specific function:: Not Available
Gene Name:: paaI
Uniprot ID:: P76084
Molecular weight:: Not Available

Phenylacetyl-CoA (ECMDB06503) (M2MDB000676)

Structure for #<Compound:0x9e8a5658>

Enzymes

Reactions

Reactions