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Showing metabocard for D-Phenyllactic acid (HMDB0000563)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:14:44 UTC
HMDB IDHMDB0000563
Secondary Accession Numbers
  • HMDB00563
Metabolite Identification
Common NameD-Phenyllactic acid
DescriptionPhenyllactic acid is a product of phenylalanine catabolism. An elevated level of phenyllactic acid is found in body fluids of patients with or phenylketonuria.
Structure
Data?1547234084
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
D-PhenyllactateGenerator
L-(-)-3-PhenyllactateGenerator
L-3-PhenyllactateGenerator
L-b-PhenyllactateGenerator
L-b-Phenyllactic acidGenerator
L-beta-PhenyllactateGenerator
L-β-phenyllactateGenerator
L-β-phenyllactic acidGenerator
(+)-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
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
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
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point122-124 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.184Not Available
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-c22a5f17e7fecfb666f2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-c22a5f17e7fecfb666f2View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01bd-2900000000-92cd31ed8e8e8e87180fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-5900000000-d1b1e4fdbfd8306c9265View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-750584951bb8866056f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-1f4cdc94d5bb4ac6489eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bc-6900000000-779d8af9b71dee9ffe5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9300000000-bb0139bf3ea8e3c03d20View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not Quantified Adult (>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
FoodDB 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 IDHFA
ChEBI ID43065
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

Enzyme Details
1. Sulfotransferase family cytosolic 2B member 1
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
Enzyme Details
2. UDP-glucuronosyltransferase 1-1
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