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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-06-10 21:22:09 UTC
HMDB IDHMDB00779
Secondary Accession NumbersNone
Metabolite Identification
Common 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 .
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-3-phenylpropionic acidChEBI
beta-Phenyllactic acidChEBI
DL-3-Phenyllactic acidChEBI
DL-beta-Phenyllactic acidChEBI
2-Hydroxy-3-phenylpropionateGenerator
2-Hydroxy-3-phenylpropanoateGenerator
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-Phenyl-2-hydroxypropanoateHMDB
3-Phenyl-2-hydroxypropanoic acidHMDB
3-PhenyllactateHMDB
3-Phenyllactic acidHMDB
a-HydroxybenzenepropanoateHMDB
a-Hydroxybenzenepropanoic acidHMDB
alpha-HydroxybenzenepropanoateHMDB
alpha-Hydroxybenzenepropanoic acidHMDB
DL-2-Hydroxy-3-phenylpropionateHMDB
DL-2-Hydroxy-3-phenylpropionic acidHMDB
PhenyllactateHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-hydroxy-3-phenylpropanoic acid
Traditional Nameβ-phenyllactic acid
CAS Registry Number828-01-3
SMILES
OC(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
InChI KeyInChIKey=VOXXWSYKYCBWHO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Benzenoid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point98 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.83HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility9.8 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.46 m3·mol-1ChemAxon
Polarizability16.7 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)splash10-0006-2930000000-9c44eea65a6e20c158eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00si-9600000000-6ba02da72bb3acc762dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0089-9700000000-901ab7fc4dce05d16406View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-017i-9100000000-248f4ab6119fb2bb911cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-cfbc3d9f0107a37ad7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00kb-1900000000-e1937415e710a88af8dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0v4i-4900000000-f7887dfe1f265bcf46baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0v4i-6900000000-7df2fcf2f9b049e4c39fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0v00-6900000000-992cb5008b3e748b7e66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0900000000-a96f38f47d5e070f0989View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-1900000000-82f893f2df7cfa6f88ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-9400000000-50e3d4b82e667ef9e4d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-37469cb4526a3ed239e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bd-4900000000-f70272565fdcdbdf5209View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9400000000-14afa00d4a96d888572bView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified3.77 +/- 1.71 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.23-0.49 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.23-0.39 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0-82.9 uMChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdult (>18 years old)BothPhenylketonuria details
UrineDetected and Quantified600.00 (200.00-1000.00) umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified149.7 +/- 208.5 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [2091926 ]
  2. Clemens PC, Schunemann MH, Hoffmann GF, Kohlschutter A: Plasma concentrations of phenyllactic acid in phenylketonuria. J Inherit Metab Dis. 1990;13(2):227-8. [2116554 ]
  3. MetaGene [Link]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022236
KNApSAcK IDNot Available
Chemspider ID3715
KEGG Compound IDC01479
BioCyc IDCPD-7999
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00779
Metagene LinkHMDB00779
METLIN ID5745
PubChem Compound3848
PDB IDNot Available
ChEBI ID25998
References
Synthesis ReferenceYu, Jian Ming; Xue, Fen. A method of synthesis of phenyllactic acid and substituted phenyllactic acids. Chinese Chemical Letters (1993), 4(8), 673-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Iijima S, Ishii A, Miyakoshi T, Odaira T, Musha M: Studies on the experimental phenylketonuria in rats. Tohoku J Exp Med. 1975 Oct;117(2):167-78. [1209606 ]
  2. Sarkissian CN, Scriver CR, Mamer OA: Measurement of phenyllactate, phenylacetate, and phenylpyruvate by negative ion chemical ionization-gas chromatography/mass spectrometry in brain of mouse genetic models of phenylketonuria and non-phenylketonuria hyperphenylalaninemia. Anal Biochem. 2000 May 1;280(2):242-9. [10790306 ]