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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:19:32 UTC
HMDB IDHMDB0000779
Secondary Accession Numbers
  • HMDB00779
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
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
PhenyllactateGenerator
3-Phenyllactic acidMeSH
3-Phenyllactic acid, monosodium saltMeSH
3-PhenyllactateMeSH
3-Phenyllactic acid, calcium saltMeSH
3-Phenyllactic acid, (D)-isomerMeSH
3-Phenyllactic acid, (DL)-isomerMeSH
3-Phenyllactic acid, (L)-isomerMeSH
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 KeyVOXXWSYKYCBWHO-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
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

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 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
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
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-2930000000-9c44eea65a6e20c158eeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0007-1910000000-1c581a4eacd9a7f2036fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-750e52d0df9e2b90be09View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9540000000-c06e2865c7cf1c780f11View 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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-cfbc3d9f0107a37ad7f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kb-1900000000-a9ac61820c9f5278e2baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v4i-4900000000-5e5e2d29a299435f9b35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v4i-6900000000-7df2fcf2f9b049e4c39fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0v00-6900000000-992cb5008b3e748b7e66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0002-0900000000-8940947cbb9a8e6253eeView 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 AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected and Quantified3.77 +/- 1.71 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.0680 +/- 0.204 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.136 +/- 0.476 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.204 +/- 0.612 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified1.0886 +/- 0.680 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified1.225 +/- 0.816 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified1.225 +/- 0.884 umol/mmol creatinineInfant (0-1 year old)BothNormal 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
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified31.297 +/- 11.566 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified361.277 +/- 500.0731 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified48.306 +/- 24.493 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified59.873 +/- 34.699 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified786.510 +/- 1020.557 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified796.0348 +/- 753.852 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria
details
UrineDetected and Quantified149.7 +/- 208.5 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
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 IDFDB022236
KNApSAcK IDNot Available
Chemspider ID3715
KEGG Compound IDC01479
BioCyc IDCPD-7999
BiGG IDNot Available
Wikipedia LinkNot Available
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. [PubMed: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. [PubMed:10790306 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Phenyllactic acid → 3-phenyl-2-(sulfooxy)propanoic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Phenyllactic acid → 6-(1-carboxy-2-phenylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Phenyllactic acid → 3,4,5-trihydroxy-6-[(2-hydroxy-3-phenylpropanoyl)oxy]oxane-2-carboxylic aciddetails