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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0000748
Secondary Accession Numbers
  • HMDB0000475
  • HMDB00475
  • HMDB00748
Metabolite Identification
Common NameL-3-Phenyllactic acid
DescriptionL-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It 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.
Structure
Data?1582752154
Synonyms
ValueSource
(R)-PhenyllactateChEBI
D-3-Phenyllactic acidChEBI
(R)-3-(Phenyl)lactateKegg
(R)-Phenyllactic acidGenerator
D-3-PhenyllactateGenerator
(R)-3-(Phenyl)lactic acidGenerator
L-3-PhenyllactateGenerator
(-)-2-Hydroxy-3-phenylpropanoateHMDB
(-)-2-Hydroxy-3-phenylpropanoic acidHMDB
(-)-2-Hydroxy-3-phenylpropionateHMDB
(-)-2-Hydroxy-3-phenylpropionic acidHMDB
(-)-3-PhenyllactateHMDB
(-)-3-Phenyllactic acidHMDB
(-)-b-PhenyllactateHMDB
(-)-b-Phenyllactic acidHMDB
(-)-beta-PhenyllactateHMDB
(-)-beta-Phenyllactic acidHMDB
(2S)-2-Hydroxy-3-phenylpropanoateHMDB
(2S)-2-Hydroxy-3-phenylpropanoic acidHMDB
(2S)-2-Hydroxy-3-phenylpropionateHMDB
(2S)-2-Hydroxy-3-phenylpropionic acidHMDB
(S)-3-Phenyl-lactateHMDB
(S)-3-Phenyl-lactic acidHMDB
(S)-3-Phenyllactic acidHMDB
(S)-a-Hydroxy-benzenepropanoateHMDB
(S)-a-Hydroxy-benzenepropanoic acidHMDB
(S)-alpha-Hydroxy-benzenepropanoateHMDB
(S)-alpha-Hydroxy-benzenepropanoic acidHMDB
(S)-b-PhenyllacticHMDB
(S)-beta-PhenyllacticHMDB
alpha-Hydroxy-beta-phenyl-propionic acidHMDB
HFAHMDB
L-(-)-3-Phenyllactic acidHMDB
L-2-Hydroxy-3-phenyl-propionic acidHMDB
L-beta-Phenyllactic acidHMDB
L-Phenyl lactateHMDB
Phenyllactic acidHMDB
(R)-3-PhenyllactateHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name(2R)-2-hydroxy-3-phenylpropanoic acid
Traditional Name(R)-phenyllactate
CAS Registry Number20312-36-1
SMILES
O[C@H](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)/t8-/m1/s1
InChI KeyVOXXWSYKYCBWHO-MRVPVSSYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point121 - 125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability16.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.29631661259
DarkChem[M-H]-135.46431661259
AllCCS[M+H]+136.53232859911
AllCCS[M-H]-134.31132859911
DeepCCS[M+H]+132.89230932474
DeepCCS[M-H]-129.52630932474
DeepCCS[M-2H]-166.74330932474
DeepCCS[M+Na]+142.28130932474
AllCCS[M+H]+136.532859911
AllCCS[M+H-H2O]+132.232859911
AllCCS[M+NH4]+140.632859911
AllCCS[M+Na]+141.832859911
AllCCS[M-H]-134.332859911
AllCCS[M+Na-2H]-135.332859911
AllCCS[M+HCOO]-136.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-3-Phenyllactic acidO[C@H](CC1=CC=CC=C1)C(O)=O2854.0Standard polar33892256
L-3-Phenyllactic acidO[C@H](CC1=CC=CC=C1)C(O)=O1466.5Standard non polar33892256
L-3-Phenyllactic acidO[C@H](CC1=CC=CC=C1)C(O)=O1528.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-3-Phenyllactic acid,1TMS,isomer #1C[Si](C)(C)O[C@H](CC1=CC=CC=C1)C(=O)O1550.2Semi standard non polar33892256
L-3-Phenyllactic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](O)CC1=CC=CC=C11500.3Semi standard non polar33892256
L-3-Phenyllactic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](CC1=CC=CC=C1)O[Si](C)(C)C1570.0Semi standard non polar33892256
L-3-Phenyllactic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](CC1=CC=CC=C1)C(=O)O1783.8Semi standard non polar33892256
L-3-Phenyllactic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)CC1=CC=CC=C11738.6Semi standard non polar33892256
L-3-Phenyllactic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2043.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-3-Phenyllactic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0007-0910000000-ee61dd1edcb64a1158352014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-3-Phenyllactic acid EI-B (Non-derivatized)splash10-0007-0920000000-7efa1766fa6121c5f6952017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-3-Phenyllactic acid GC-EI-TOF (Non-derivatized)splash10-0007-0910000000-ee61dd1edcb64a1158352017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-750e52d0df9e2b90be092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9540000000-c06e2865c7cf1c780f112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-0900000000-c20feab32f47edc5bb942012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0f89-9500000000-598d564a5c5cb5a6febb2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0ac0-9000000000-32b5f6f43141f16996a42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOFsplash10-0kmi-1900000000-9df5ce396877a246e75a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOFsplash10-0ufr-5900000000-3ebebc6c015723d2e26d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOFsplash10-014i-0900000000-09797df3a57ff3212fae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOFsplash10-004i-9000000000-55faf2887a4699d775df2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOFsplash10-002f-9000000000-5e9184f3d8f3a1c84cb52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-1900000000-2173c51c5d8f4369c56a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOFsplash10-014r-1900000000-30445b1c1ad4ff6c6cfe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOFsplash10-014i-0900000000-68f9968ec4336192e0932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOFsplash10-00mo-9400000000-3fc7b7dbdcdb0c24a7182021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOFsplash10-00ke-1900000000-b4165543fe4077bc88782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOFsplash10-006y-4900000000-9cc77ecfa0e908d400f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOFsplash10-0006-9100000000-8e08ba85783d44c725b82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-0900000000-c5b01c647718505d882a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOFsplash10-01bd-2900000000-2cd5c47ea7b35f76e87b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOFsplash10-00mo-9300000000-22457d19a65466f8e94d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOFsplash10-00dl-5900000000-eb26ccce0382619681682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOFsplash10-0006-9300000000-aa44337c740dacf05e9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOFsplash10-0006-9100000000-6509f4478fff1766b65a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-3900000000-15a50bcc903d54af3f432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOFsplash10-0006-9400000000-0d7b49d15700ae2666452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOFsplash10-0006-9300000000-ca99933d289067e5347a2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.427 +/- 0.354 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.596 +/- 0.337 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0-82.9 uMChildren (1-13 years old)BothPhenylketonuria details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  1. Clemens PC, Schunemann MH, Hoffmann GF, Kohlschutter A: Plasma concentrations of phenyllactic acid in phenylketonuria. J Inherit Metab Dis. 1990;13(2):227-8. [PubMed:2116554 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022220
KNApSAcK IDC00000150
Chemspider ID558480
KEGG Compound IDC05607
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound643327
PDB IDNot Available
ChEBI ID32978
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tekewe A, Singh S, Singh M, Mohan U, Banerjee UC: Development and validation of HPLC method for the resolution of drug intermediates: DL-3-Phenyllactic acid, DL-O-acetyl-3-phenyllactic acid and (+/-)-mexiletine acetamide enantiomers. Talanta. 2008 Mar 15;75(1):239-45. doi: 10.1016/j.talanta.2007.11.004. Epub 2007 Nov 13. [PubMed:18371874 ]
  2. (). Andrew D. Abell, John W. Blunt, Glenn J. Foulds and Murray H. G. Munro Chemistry of the mycalamides: antiviral and antitumour compounds from a New Zealand marine sponge. Part 6.1–3 The synthesis and testing of analogues of the C(7)–C(10) fragment. J. Chem. Soc., Perkin Trans. 1, 1997, 1647 - 1654,. .