Record Information
Version1.0
Creation date2011-09-21 00:10:41 UTC
Update date2015-10-09 22:30:16 UTC
Primary IDFDB022236
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhenyllactic acid
DescriptionPhenyllactic acid a product of phenylalanine catabolism, appearing prominently in the urine in individuals with phenylketonuria. Levels of several phenylalanine metabolites, including phenylacetate (PAA), phenyllactate (PLA), and phenylpyruvate (PPA)) are elevated in Phenylketonuria (PKU) (OMIM 261600). Phenyllactic acid is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid and then to phenyllactate through the action of lactate dehydrogenase. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. PMID: 10790306; OMIM: 261600 [HMDB]
CAS Number828-01-3
Structure
Thumb
Synonyms
SynonymSource
2-Hydroxy-2-phenylpropionic acidChEBI
2-Phenyllactic acidChEBI
alpha-Hydroxy-alpha-methylbenzeneacetic acidChEBI
alpha-Hydroxy-alpha-phenylpropionic acidChEBI
alpha-Methylmandelic acidChEBI
2-Hydroxy-2-phenylpropionateGenerator
2-PhenyllactateGenerator
a-Hydroxy-a-methylbenzeneacetateGenerator
a-Hydroxy-a-methylbenzeneacetic acidGenerator
alpha-Hydroxy-alpha-methylbenzeneacetateGenerator
Α-hydroxy-α-methylbenzeneacetateGenerator
Α-hydroxy-α-methylbenzeneacetic acidGenerator
a-Hydroxy-a-phenylpropionateGenerator
a-Hydroxy-a-phenylpropionic acidGenerator
alpha-Hydroxy-alpha-phenylpropionateGenerator
Α-hydroxy-α-phenylpropionateGenerator
Α-hydroxy-α-phenylpropionic acidGenerator
a-MethylmandelateGenerator
a-Methylmandelic acidGenerator
alpha-MethylmandelateGenerator
Α-methylmandelateGenerator
Α-methylmandelic acidGenerator
PhenyllactateGenerator
Atrolactic acid, (+-)-isomerMeSH
Hydroxyphenylpropionic acidMeSH
Atrolactic acidMeSH
Atrolactic acid monosodium salt, (S)-isomerMeSH
HMMAMeSH
Hydroxymethylmandelic acidMeSH
2-Hydroxy-3-phenylpropionic acidChEBI
beta-Phenyllactic acidChEBI
DL-3-Phenyllactic acidChEBI
DL-beta-Phenyllactic acidChEBI
2-Hydroxy-3-phenylpropionateGenerator
b-PhenyllactateGenerator
b-Phenyllactic acidGenerator
beta-PhenyllactateGenerator
β-phenyllactateGenerator
β-phenyllactic acidGenerator
DL-3-PhenyllactateGenerator
DL-b-PhenyllactateGenerator
DL-b-Phenyllactic acidGenerator
DL-beta-PhenyllactateGenerator
DL-β-phenyllactateGenerator
DL-β-phenyllactic acidGenerator
3-Phenyllactic acidMeSH, HMDB
3-Phenyllactic acid, monosodium saltMeSH, HMDB
3-PhenyllactateMeSH, Generator, HMDB
3-Phenyllactic acid, calcium saltMeSH, HMDB
3-Phenyllactic acid, (D)-isomerMeSH, HMDB
3-Phenyllactic acid, (DL)-isomerMeSH, HMDB
3-Phenyllactic acid, (L)-isomerMeSH, HMDB
2-Hydroxy-3-(phenyl)propanoic acidHMDB
3-(Phenyl)-2-hydroxypropanoic acidHMDB
2-Hydroxy-3-phenylpropanoatehmdb
2-Hydroxy-3-phenylpropanoic acidhmdb
3-Phenyl-2-hydroxypropanoatehmdb
3-Phenyl-2-hydroxypropanoic acidhmdb
a-Hydroxybenzenepropanoatehmdb
a-Hydroxybenzenepropanoic acidhmdb
alpha-Hydroxybenzenepropanoatehmdb
alpha-Hydroxybenzenepropanoic acidhmdb
DL-2-Hydroxy-3-phenylpropionatehmdb
DL-2-Hydroxy-3-phenylpropionic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility9.8 g/LALOGPS
logP0.84ALOGPS
logP1.18ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.46 m³·mol⁻¹ChemAxon
Polarizability16.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O3
IUPAC name2-hydroxy-3-phenylpropanoic acid
InChI IdentifierInChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
InChI KeyVOXXWSYKYCBWHO-UHFFFAOYSA-N
Isomeric SMILESOC(CC1=CC=CC=C1)C(O)=O
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
Classification
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
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Foods
  • Dairy products
  • Eggs
  • Meats
  • Grains:

    Nuts and legumes:

    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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSPhenyllactic acid, 2 TMS, GC-MS Spectrumsplash10-0006-2930000000-9c44eea65a6e20c158eeSpectrum
    GC-MSPhenyllactic acid, non-derivatized, GC-MS Spectrumsplash10-0006-2930000000-9c44eea65a6e20c158eeSpectrum
    GC-MSPhenyllactic acid, non-derivatized, GC-MS Spectrumsplash10-0007-1910000000-1c581a4eacd9a7f2036fSpectrum
    Predicted GC-MSPhenyllactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9300000000-750e52d0df9e2b90be09Spectrum
    Predicted GC-MSPhenyllactic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9540000000-c06e2865c7cf1c780f11Spectrum
    Predicted GC-MSPhenyllactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPhenyllactic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPhenyllactic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPhenyllactic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPhenyllactic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPhenyllactic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-cfbc3d9f0107a37ad7f72012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00kb-1900000000-e1937415e710a88af8db2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0v4i-4900000000-f7887dfe1f265bcf46ba2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0v4i-6900000000-7df2fcf2f9b049e4c39f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0v00-6900000000-992cb5008b3e748b7e662012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-cfbc3d9f0107a37ad7f72017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kb-1900000000-a9ac61820c9f5278e2ba2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v4i-4900000000-5e5e2d29a299435f9b352017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v4i-6900000000-7df2fcf2f9b049e4c39f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v00-6900000000-992cb5008b3e748b7e662017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0002-0900000000-8940947cbb9a8e6253ee2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00si-9600000000-6ba02da72bb3acc762df2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0089-9700000000-901ab7fc4dce05d164062012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-017i-9100000000-248f4ab6119fb2bb911c2012-07-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-37469cb4526a3ed239e92015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bd-4900000000-f70272565fdcdbdf52092015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9400000000-14afa00d4a96d888572b2015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-15a50bcc903d54af3f432021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000000-0d7b49d15700ae2666452021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-ca99933d289067e5347a2021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0900000000-a96f38f47d5e070f09892015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1900000000-82f893f2df7cfa6f88eb2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-9400000000-50e3d4b82e667ef9e4d12015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-5900000000-eb26ccce0382619681682021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-aa44337c740dacf05e9c2021-09-24View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID3715
    ChEMBL IDCHEMBL1778420
    KEGG Compound IDC01479
    Pubchem Compound ID3848
    Pubchem Substance IDNot Available
    ChEBI ID25998
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB00779
    CRC / DFC (Dictionary of Food Compounds) IDDCD49-C:HMP99-J
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    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
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference