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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:02 UTC
HMDB IDHMDB0000563
Secondary Accession Numbers
  • HMDB00563
Metabolite Identification
Common NameD-Phenyllactic acid
DescriptionD-Phenyllactic acid, also known as L-3-phenyllactate, 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. D-Phenyllactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752140
Synonyms
ValueSource
ALPHA-HYDROXY-BETA-phenyl-propionIC ACIDChEBI
L-(-)-3-Phenyllactic acidChEBI
L-3-Phenyllactic acidChEBI
L-beta-Phenyllactic acidChEBI
a-HYDROXY-b-phenyl-propionateGenerator
a-HYDROXY-b-phenyl-propionic acidGenerator
alpha-HYDROXY-beta-phenyl-propionateGenerator
Α-hydroxy-β-phenyl-propionateGenerator
Α-hydroxy-β-phenyl-propionic acidGenerator
L-(-)-3-PhenyllactateGenerator
L-3-PhenyllactateGenerator
L-b-PhenyllactateGenerator
L-b-Phenyllactic acidGenerator
L-beta-PhenyllactateGenerator
L-Β-phenyllactateGenerator
L-Β-phenyllactic acidGenerator
D-PhenyllactateGenerator
(+)-2-Hydroxy-3-phenylpropionateHMDB
(+)-2-Hydroxy-3-phenylpropionic acidHMDB
(+)-3-PhenyllactateHMDB
(+)-3-Phenyllactic acidHMDB
(+)-b-PhenyllactateHMDB
(+)-b-Phenyllactic acidHMDB
(+)-beta-PhenyllactateHMDB
(+)-beta-Phenyllactic acidHMDB
(2R)-2-Hydroxy-2-phenylpropanoateHMDB
(2R)-2-Hydroxy-2-phenylpropanoic acidHMDB
(2R)-2-Hydroxy-2-phenylpropionateHMDB
(2R)-2-Hydroxy-2-phenylpropionic acidHMDB
(R)-2-Hydroxy-2-phenylpropionateHMDB
(R)-2-Hydroxy-2-phenylpropionic acidHMDB
(R)-2-Phenyl-2-hydroxypropanoateHMDB
(R)-2-Phenyl-2-hydroxypropanoic acidHMDB
(R)-3-Phenyl-lactateHMDB
(R)-3-Phenyl-lactic acidHMDB
(R)-3-PhenyllactateHMDB
(R)-3-Phenyllactic acidHMDB
(R)-a-Hydroxy-3-phenylpropionateHMDB
(R)-a-Hydroxy-3-phenylpropionic acidHMDB
(R)-a-Hydroxy-benzenepropanoateHMDB
(R)-a-Hydroxy-benzenepropanoic acidHMDB
(R)-alpha-Hydroxy-3-phenylpropionateHMDB
(R)-alpha-Hydroxy-3-phenylpropionic acidHMDB
(R)-alpha-Hydroxy-benzenepropanoateHMDB
(R)-alpha-Hydroxy-benzenepropanoic acidHMDB
(R)-b-PhenyllactateHMDB
(R)-b-Phenyllactic acidHMDB
(R)-beta-PhenyllactateHMDB
(R)-beta-Phenyllactic acidHMDB
(R)-PhenyllactateHMDB
(R)-Phenyllactic acidHMDB
b-Phenyl-D-lactateHMDB
b-Phenyl-D-lactic acidHMDB
beta-Phenyl-delta-lactateHMDB
beta-Phenyl-delta-lactic acidHMDB
D-2-Hydroxy-3-phenylpropionateHMDB
D-2-Hydroxy-3-phenylpropionic acidHMDB
D-3-PhenyllactateHMDB
D-3-Phenyllactic acidHMDB
D-b-PhenyllactateHMDB
D-b-Phenyllactic acidHMDB
delta-2-Hydroxy-3-phenylpropionateHMDB
delta-2-Hydroxy-3-phenylpropionic acidHMDB
delta-3-PhenyllactateHMDB
delta-3-Phenyllactic acidHMDB
delta-beta-PhenyllactateHMDB
delta-beta-Phenyllactic acidHMDB
delta-PhenyllactateHMDB
delta-Phenyllactic acidHMDB
(S)-3-PhenyllactateHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name(2S)-2-hydroxy-3-phenylpropanoic acid
Traditional NameL-3-phenyllactic acid
CAS Registry Number7326-19-4
SMILES
[H][C@](O)(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-/m0/s1
InChI KeyVOXXWSYKYCBWHO-QMMMGPOBSA-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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point122-124 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.184Not 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
Polarizability16.7 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]+136.67731661259
DarkChem[M-H]-134.92231661259
AllCCS[M+H]+136.56332859911
AllCCS[M-H]-134.31132859911
DeepCCS[M+H]+131.49130932474
DeepCCS[M-H]-129.15530932474
DeepCCS[M-2H]-164.69830932474
DeepCCS[M+Na]+139.15630932474

Predicted Kovats Retention Indices

Underivatized

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

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Phenyllactic acid,1TMS,isomer #1C[Si](C)(C)O[C@@H](CC1=CC=CC=C1)C(=O)O1550.2Semi standard non polar33892256
D-Phenyllactic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](O)CC1=CC=CC=C11500.3Semi standard non polar33892256
D-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
D-Phenyllactic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H](CC1=CC=CC=C1)C(=O)O1783.8Semi standard non polar33892256
D-Phenyllactic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O)CC1=CC=CC=C11738.6Semi standard non polar33892256
D-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 - D-Phenyllactic acid EI-B (Non-derivatized)splash10-0006-9100000000-c22a5f17e7fecfb666f22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Phenyllactic acid EI-B (Non-derivatized)splash10-0006-9100000000-c22a5f17e7fecfb666f22018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-750e52d0df9e2b90be092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9540000000-c06e2865c7cf1c780f112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-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 - D-Phenyllactic acid 35V, Negative-QTOFsplash10-0gb9-1900000000-cc48c5ff57b37ce10c092021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 10V, Positive-QTOFsplash10-01bd-2900000000-92cd31ed8e8e8e87180f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 20V, Positive-QTOFsplash10-006x-5900000000-d1b1e4fdbfd8306c92652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 40V, Positive-QTOFsplash10-0006-9100000000-750584951bb8866056f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-2900000000-1f4cdc94d5bb4ac6489e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 20V, Negative-QTOFsplash10-01bc-6900000000-779d8af9b71dee9ffe5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 40V, Negative-QTOFsplash10-004l-9300000000-bb0139bf3ea8e3c03d202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 10V, Positive-QTOFsplash10-00dl-5900000000-eb26ccce0382619681682021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 20V, Positive-QTOFsplash10-0006-9300000000-aa44337c740dacf05e9c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 40V, Positive-QTOFsplash10-0006-9100000000-6509f4478fff1766b65a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-3900000000-15a50bcc903d54af3f432021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 20V, Negative-QTOFsplash10-0006-9400000000-0d7b49d15700ae2666452021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 40V, Negative-QTOFsplash10-0006-9300000000-ca99933d289067e5347a2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
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 IDDB02494
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05607
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5547
PubChem Compound444718
PDB IDNot Available
ChEBI ID43065
Food Biomarker OntologyNot Available
VMH IDPLAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKamata, Masahiro; Toyomasu, Ryuta; Suzuki, Eiichiro; Tanaka, Takashi. D-Phenyllactic acid production by Brevibacterium or Corynebacterium. Jpn. Kokai Tokkyo Koho (1986), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

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
D-Phenyllactic acid → (2S)-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
D-Phenyllactic acid → 6-[(1R)-1-carboxy-2-phenylethoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
D-Phenyllactic acid → 3,4,5-trihydroxy-6-{[(2S)-2-hydroxy-3-phenylpropanoyl]oxy}oxane-2-carboxylic aciddetails