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Identification
YMDB IDYMDB00891
NamePhenylacetic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhenylacetic acid, also known as phenylacetate or alpha-toluic acid, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenylacetic acid is a weakly acidic compound (based on its pKa). Phenylacetic acid exists in all living species, ranging from bacteria to humans. Phenylacetic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-Phenylacetate
  • 2-Phenylacetic acid
  • 2-phenylethanoate
  • 2-phenylethanoic acid
  • a-Toluate
  • a-Toluic acid
  • alpha-Toluate
  • alpha-Toluic acid
  • Benzeneacetate
  • Benzeneacetic acid
  • Benzylformate
  • Benzylformic acid
  • omega-Phenylacetate
  • omega-Phenylacetic acid
  • Phenylacetate
  • Phenylacetic acid
  • Phenylethanoate
  • Phenylethanoic acid
  • w-Phenylacetate
  • w-Phenylacetic acid
  • PA
  • Α-toluate
  • Α-toluic acid
  • Phenylacetic acid, potassium salt
  • Sodium phenylacetate
  • Phenylacetic acid, lithium salt
  • Phenylacetic acid, sodium salt
  • Phenylacetic acid, ammonium salt
  • Phenylacetic acid, calcium salt
  • Phenylacetic acid, cesium salt
  • Phenylacetic acid, mercury salt
  • Phenylacetic acid, rubidium salt
  • Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPD
  • (2S)-6-(Acetylamino)-2-aminohexanoic acid
  • N(6)-ACETYLLYSINE
  • N(zeta)-Acetyllysine
  • N-epsilon-Acetyl-L-lysine
  • N-Epsilon-Acetyllysine
  • N(epsilon)-Acetyl-L-lysine
  • N(zeta)-Acetyl-L-lysine
  • (2S)-6-(Acetylamino)-2-aminohexanoate
  • N(Z)-Acetyllysine
  • N(Ζ)-acetyllysine
  • N(Z)-Acetyl-L-lysine
  • N(Ζ)-acetyl-L-lysine
  • e-Acetyl-L-lysine
  • e-N-Acetyl-L-lysine
  • e-N-Acetyllysine
  • epsilon-Acetyl-L-lysine
  • epsilon-N-Acetyl-L-lysine
  • epsilon-N-Acetyllysine
  • L-e-N-Acetyllysine
  • L-epsilon-N-Acetyllysine
  • N-e-Acetyl-L-lysine
  • N-e-Acetyllysine
  • N6-Acetyllysine
  • Ne-acetyl-L-lysine
  • Ne-acetyllysine
  • Omega-N-acetyl-L-lysine
  • W-N-Acetyl-L-lysine
  • N(6)-Acetyllsine
  • Omega-acetyllsine
  • 1,1-Ethanedicarboxylic acid
  • 2-Methylmalonic acid
  • alpha-Methylmalonic acid
  • Isosuccinic acid
  • 1,1-Ethanedicarboxylate
  • 2-Methylmalonate
  • a-Methylmalonate
  • a-Methylmalonic acid
  • alpha-Methylmalonate
  • Α-methylmalonate
  • Α-methylmalonic acid
  • Isosuccinate
  • Methylmalonate
  • Methyl-malonate
  • Methyl-malonic acid
  • Methyl-propanedioate
  • Methyl-propanedioic acid
  • Methylpropanedioate
  • Methylpropanedioic acid
  • Acid, methylmalonic
  • 2-Ketoglutaric acid
  • alpha-Ketoglutaric acid
  • 2-Ketoglutarate
  • a-Ketoglutarate
  • a-Ketoglutaric acid
  • alpha-Ketoglutarate
  • Α-ketoglutarate
  • Α-ketoglutaric acid
  • Oxoglutarate
  • 2-oxo-1,5-Pentanedioate
  • 2-oxo-1,5-Pentanedioic acid
  • 2-Oxoglutarate
  • 2-Oxoglutaric acid
  • 2-Oxopentanedioate
  • 2-Oxopentanedioic acid
  • alpha-Ketoglutaric acid, calcium salt (2:1)
  • alpha-Ketoglutaric acid, sodium salt
  • Calcium alpha-ketoglutarate
  • alpha-Ketoglutaric acid, disodium salt
  • alpha-Ketoglutaric acid, monosodium salt
  • Calcium ketoglutarate
  • alpha-Ketoglutaric acid, diammonium salt
  • alpha-Ketoglutaric acid, dipotassium salt
  • alpha-Ketoglutaric acid, monopotassium salt
  • alpha-Ketoglutaric acid, potassium salt
  • alpha-Oxoglutarate
  • Oxogluric acid
  • 2 Oxoglutaric acid
  • Calcium alpha ketoglutarate
  • Ketoglutaric acid
  • alpha Ketoglutaric acid
  • alpha Ketoglutaric acid, potassium salt
  • 2 Ketoglutaric acid
  • alpha Ketoglutarate
  • alpha Ketoglutaric acid, diammonium salt
  • alpha Ketoglutaric acid, dipotassium salt
  • alpha Ketoglutaric acid, sodium salt
  • alpha Oxoglutarate
  • 2 Ketoglutarate
  • alpha Ketoglutaric acid, disodium salt
  • alpha Ketoglutaric acid, monosodium salt
  • alpha-Ketoglutarate, calcium
  • 2 Oxoglutarate
  • Ketoglutaric acids
  • Oxoglutarates
  • alpha Ketoglutaric acid, monopotassium salt
  • (9Z)-Octadecenoic acid
  • (Z)-Octadec-9-enoic acid
  • 18:1 N-9
  • 18:1DElta9cis
  • C18:1 N-9
  • cis-9-Octadecenoic acid
  • cis-Delta(9)-Octadecenoic acid
  • cis-Oleic acid
  • FA 18:1
  • Octadec-9-enoic acid
  • Oelsaeure
  • Oleate
  • (9Z)-Octadecenoate
  • (Z)-Octadec-9-enoate
  • cis-9-Octadecenoate
  • cis-delta(9)-Octadecenoate
  • cis-Δ(9)-octadecenoate
  • cis-Δ(9)-octadecenoic acid
  • cis-Oleate
  • Octadec-9-enoate
  • (9Z)-9-Octadecenoate
  • (9Z)-9-Octadecenoic acid
  • (Z)-9-Octadecanoate
  • (Z)-9-Octadecanoic acid
  • 9,10-Octadecenoate
  • 9,10-Octadecenoic acid
  • 9-(Z)-Octadecenoate
  • 9-(Z)-Octadecenoic acid
  • 9-Octadecenoate
  • 9-Octadecenoic acid
  • Century CD fatty acid
  • cis-Octadec-9-enoate
  • cis-Octadec-9-enoic acid
  • Distoline
  • Emersol 210
  • Emersol 211
  • Emersol 213
  • Emersol 220 white oleate
  • Emersol 220 white oleic acid
  • Emersol 221 low titer white oleate
  • Emersol 221 low titer white oleic acid
  • Emersol 233LL
  • Emersol 6321
  • Emersol 6333 NF
  • Emersol 7021
  • Glycon ro
  • Glycon wo
  • Groco 2
  • Groco 4
  • Groco 5l
  • Groco 6
  • Industrene 104
  • Industrene 105
  • Industrene 205
  • Industrene 206
  • L'acide oleique
  • Metaupon
  • Oelsauere
  • Oleic acid extra pure
  • Oleinate
  • Oleinic acid
  • Pamolyn
  • Pamolyn 100
  • Pamolyn 100 FG
  • Pamolyn 100 FGK
  • Pamolyn 125
  • Priolene 6900
  • Red oil
  • Tego-oleic 130
  • Vopcolene 27
  • Wecoline oo
  • Z-9-Octadecenoate
  • Z-9-Octadecenoic acid
  • Acid, 9-octadecenoic
  • Acid, oleic
  • 9 Octadecenoic acid
  • Acid, cis-9-octadecenoic
  • cis 9 Octadecenoic acid
  • FA(18:1(9Z))
  • (S)-2-Aminobutanedioic acid
  • (S)-2-Aminosuccinic acid
  • 2-Aminosuccinic acid
  • Asp
  • ASPARTIC ACID
  • D
  • L-Asparaginsaeure
  • L-Asp
  • (S)-2-Aminobutanedioate
  • (S)-2-Aminosuccinate
  • 2-Aminosuccinate
  • ASPARTate
  • L-Aspartate
  • (+)-Aspartate
  • (+)-Aspartic acid
  • (2S)-Aspartate
  • (2S)-Aspartic acid
  • (L)-Aspartate
  • (L)-Aspartic acid
  • (R)-2-Aminosuccinate
  • (S)-(+)-Aspartate
  • (S)-(+)-Aspartic acid
  • (S)-Amino-butanedioate
  • (S)-Amino-butanedioic acid
  • (S)-Aminobutanedioate
  • (S)-Aminobutanedioic acid
  • (S)-Aspartate
  • (S)-Aspartic acid
  • 2-Amino-3-methylsuccinate
  • 2-Amino-3-methylsuccinic acid
  • alpha-Aminosuccinate
  • alpha-Aminosuccinic acid
  • Aminosuccinate
  • Asparagate
  • Asparagic acid
  • Asparaginate
  • Asparaginic acid
  • Asparatate
  • H-Asp-OH
  • L-(+)-Aspartate
  • L-(+)-Aspartic acid
  • L-Aminosuccinate
  • L-Aminosuccinic acid
  • L-Asparagate
  • L-Asparagic acid
  • L-Asparaginate
  • L-Asparaginic acid
  • (+-)-Aspartic acid
  • (R,S)-Aspartic acid
  • Aspartate, disodium
  • Aspartate, magnesium
  • Aspartate, monopotassium
  • Aspartic acid, dipotassium salt
  • Aspartic acid, hydrobromide
  • Aspartic acid, monopotassium salt
  • Aspartic acid, monosodium salt
  • Aspartic acid, potassium salt
  • L Aspartate
  • MG5Longoral
  • Potassium aspartate
  • Polysuccinimide
  • Ammonium aspartate
  • Aspartate, ammonium
  • Aspartate, calcium
  • Aspartate, monosodium
  • Aspartic acid, calcium salt
  • Aspartic acid, disodium salt
  • Aspartic acid, magnesium (1:1) salt, hydrochloride, trihydrate
  • Dipotassium aspartate
  • Disodium aspartate
  • Hydrochloride, aspartate magnesium
  • Monopotassium aspartate
  • Sodium aspartate
  • Aspartate, dipotassium
  • Aspartic acid, magnesium (2:1) salt
  • Aspartic acid, sodium salt
  • Hydrobromide aspartic acid
  • Magnesium aspartate
  • MG 5 Longoral
  • Monosodium aspartate
  • Aspartate magnesium hydrochloride
  • Aspartate, potassium
  • Aspartate, sodium
  • Aspartic acid, ammonium salt
  • Aspartic acid, hydrochloride
  • Aspartic acid, magnesium-potassium (2:1:2) salt
  • Calcium aspartate
  • Hydrochloride aspartic acid
  • L Aspartic acid
  • Magnesiocard
  • MG-5-Longoral
  • Poly-DL-succinimide
  • (2R)-1-(Hydrogen phosphonatooxy)-3-(octanoyloxy)propan-2-yl octanoic acid
  • DMA
  • HNMe2
  • Me2nh
  • N,N-Dimethylamine
  • (CH3)2nh
  • Dimethylamine anhydrous
  • Dimethylamine anhydrous (dot)
  • Dimethylamine aqueous solution
  • Dimethylamine hydrobromide
  • Dimethylamine solution
  • N-Methyl-methanamine
  • N-Methylmethanamine
  • N-Methylmethanamine (acd/name 4.0)
  • Dimethylamine nitrate
  • Dimethylamine perchlorate
  • Dimethylamine sulfate
  • Dimethylamine hydrochloride
  • Dimethylamine phosphate (3:1)
  • Dimethylamine, conjugate acid
  • Dimethylammonium chloride
  • Dimethylamine sulfate (1:1)
  • Dimethylammonium formate
  • Dimethylamine monosulfate
  • 6(1H)-Purinone
  • 6-Oxopurine
  • 9H-Purin-6(1H)-one
  • Hyp
  • Purin-6(1H)-one
  • Purine-6-ol
  • 1,7-Dihydro-6H-purin-6-one
  • 1,7-Dihydro-6H-purine-6-one
  • 1H,7H-Hypoxanthine
  • 3H-Purin-6-ol
  • 4-Hydroxy-1H-purine
  • 6-Hydroxy-1H-purine
  • 6-Hydroxypurine
  • 7H-Purin-6-ol
  • 9H-Purin-6-ol
  • Hypoxanthine enol
  • Purin-6(3H)-one
  • Purin-6-ol
  • Sarcine
  • Sarkin
  • Sarkine
CAS number103-82-2
WeightAverage: 136.1479
Monoisotopic: 136.0524295
InChI KeyWLJVXDMOQOGPHL-UHFFFAOYSA-N
InChIInChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
IUPAC Name2-phenylacetic acid
Traditional IUPAC Nameω-phenylacetic acid
Chemical FormulaC8H8O2
SMILES[H]OC(=O)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point76.7 °C
Experimental Properties
PropertyValueReference
Water Solubility16.6 mg/mL at 20 oC [CHIOU,CT et al. (1977)]PhysProp
LogP1.41 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.61 g/LALOGPS
logP1.72ALOGPS
logP1.61ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.37 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
CivetFDB031100
FloralFDB031100
FlowerFDB031100
HoneyFDB031100
HoneysuckleFDB031100
SourFDB031100
SweetFDB031100
WaxyFDB031100
SMPDB Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine metabolismec00360 Map00360
SMPDB ReactionsNot Available
KEGG Reactions
Phenylacetaldehyde + NAD + waterNADH + hydron + Phenylacetic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9700000000-c07461cdad68959aa53fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-de65c7c0092343a4e599JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9700000000-c07461cdad68959aa53fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-9700000000-43e86e45beae2fa6704fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-dc43e5e062b0ed500c5fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9100000000-aaef76d181aebe492bbeJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9100000000-de65c7c0092343a4e599JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-9000000000-6ca33b098558bf13801cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f898aafe4cecc87d26f1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2900000000-94a6f40f937bf9d7e4c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9500000000-8d3540e40bfc0e4c0e5fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-417ad1f13a593ac780b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-5900000000-0ed04a623daaf32fffdaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-8900000000-709928d6b823240d3528JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-4a7739132344f3dec710JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1e23fd8e6ce900cd8e4cJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Vuralhan, Z., Morais, M. A., Tai, S. L., Piper, M. D., Pronk, J. T. (2003). "Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae." Appl Environ Microbiol 69:4534-4541.12902239
Synthesis Reference:Zhou, Shu-jing; Li, Jin-lian; Luan, Fang. New synthetic method for benzeneacetic acid. Huaxue Yu Shengwu Gongcheng (2005), 22(2), 43-44.
External Links:
ResourceLink
CHEBI ID30745
HMDB IDHMDB00209
Pubchem Compound ID999
Kegg IDC07086
ChemSpider ID10181341
FOODB IDFDB031100
WikipediaPhenylacetic_acid
BioCyc IDPHENYLACETATE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD2
Uniprot ID:
P47771
Molecular weight:
55187.39844
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD3
Uniprot ID:
P54114
Molecular weight:
55384.80078
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.