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Record Information
Version3.6
Creation Date2008-10-02 13:30:03 UTC
Update Date2016-02-11 01:20:02 UTC
HMDB IDHMDB10715
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Phenylacetamide
Description2-Phenylacetamide is an intermediate in phenylalanine metabolism and styrene degradation(KEGG ID C02505). It is the third to last step in the synthesis of phenylacetylglutamine and is converted from phenylalanine via the enzyme phenylalanine 2-monooxygenase [EC:1.13.12.9]. It is then converted to phenylacetate via the enzyme amidase [EC:3.5.1.4].
Structure
Thumb
Synonyms
ValueSource
alpha-PhenylacetamideChEBI
alpha-ToluamideChEBI
BenzeneacetamideChEBI
Phenyl-beta-acetylamineChEBI
PhenylacetamideChEBI
Phenylacetic acid amideChEBI
a-PhenylacetamideGenerator
α-phenylacetamideGenerator
a-ToluamideGenerator
α-toluamideGenerator
Phenyl-b-acetylamineGenerator
Phenyl-β-acetylamineGenerator
Phenylacetate amideGenerator
(alpha-)2-PhenylacetamideHMDB
2-Phenyl-acetamideHMDB
alpha-Toluimidic acidHMDB
beta-Phenyl-acetylamineHMDB
Chemical FormulaC8H9NO
Average Molecular Weight135.1632
Monoisotopic Molecular Weight135.068413915
IUPAC Name2-phenylacetamide
Traditional Namephenylacetamide
CAS Registry Number103-81-1
SMILES
NC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
InChI KeyInChIKey=LSBDFXRDZJMBSC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetamides
Direct ParentPhenylacetamides
Alternative Parents
Substituents
  • Phenylacetamide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.84 mg/mLALOGPS
logP0.64ALOGPS
logP0.8ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)16.5ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.19 m3·mol-1ChemAxon
Polarizability14.17 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000l-6900000000-3cbbf18204f4b2de0705View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9200000000-55ad84b73efd28e15062View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027865
KNApSAcK IDNot Available
Chemspider ID7397
KEGG Compound IDC02505
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10715
Metagene LinkHMDB10715
METLIN IDNot Available
PubChem Compound7680
PDB IDNot Available
ChEBI ID16562
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
May contribute to airway host defense against infection.
Gene Name:
LPO
Uniprot ID:
P22079
Molecular weight:
70983.6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
Reactions
L-Phenylalanine + Oxygen → 2-Phenylacetamide + Carbon dioxidedetails
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
General function:
Involved in peroxidase activity
Specific function:
Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
Gene Name:
EPX
Uniprot ID:
P11678
Molecular weight:
81039.5