Showing metabocard for Hydroxyphenyllactic acid (BMDB0000755)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:05 UTC
Update Date2020-05-11 20:47:57 UTC
BMDB IDBMDB0000755
Secondary Accession Numbers
  • BMDB00755
Metabolite Identification
Common NameHydroxyphenyllactic acid
Description3-(4-Hydroxyphenyl)lactic acid, also known as 4-hydroxyphenyllactate or hpla, 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. 3-(4-Hydroxyphenyl)lactic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-(4-Hydroxyphenyl)lactic acid exists in all eukaryotes, ranging from yeast to humans. 3-(4-Hydroxyphenyl)lactic acid is a potentially toxic compound. 3-(4-Hydroxyphenyl)lactic acid has been found to be associated with several diseases known as eosinophilic esophagitis, colorectal cancer, and supradiaphragmatic malignancy; also 3-(4-hydroxyphenyl)lactic acid has been linked to the inborn metabolic disorders including phenylketonuria.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Hydroxy-3-(4-hydroxyphenyl)propanoateChEBI
2-Hydroxy-3-(p-hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenyllactic acidChEBI
beta-(4-Hydroxyphenyl)lactic acidChEBI
beta-(p-Hydroxyphenyl)lactic acidChEBI
DL-p-Hydroxyphenyllactic acidChEBI
p-Hydroxyphenyl lactic acidChEBI
4-HydroxyphenyllactateKegg
p-HydroxyphenyllactateKegg
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acidGenerator
2-Hydroxy-3-(p-hydroxyphenyl)propionateGenerator
b-(4-Hydroxyphenyl)lactateGenerator
b-(4-Hydroxyphenyl)lactic acidGenerator
beta-(4-Hydroxyphenyl)lactateGenerator
Β-(4-hydroxyphenyl)lactateGenerator
Β-(4-hydroxyphenyl)lactic acidGenerator
b-(p-Hydroxyphenyl)lactateGenerator
b-(p-Hydroxyphenyl)lactic acidGenerator
beta-(p-Hydroxyphenyl)lactateGenerator
Β-(p-hydroxyphenyl)lactateGenerator
Β-(p-hydroxyphenyl)lactic acidGenerator
DL-p-HydroxyphenyllactateGenerator
p-Hydroxyphenyl lactateGenerator
p-Hydroxyphenyllactic acidGenerator
HydroxyphenyllactateGenerator
(RS)-3-(4-Hydroxyphenyl)lactateHMDB
(RS)-3-(4-Hydroxyphenyl)lactic acidHMDB
3-(4-Hydroxyphenyl)-DL-lactateHMDB
3-(4-Hydroxyphenyl)-DL-lactic acidHMDB
3-(4-Hydroxyphenyl)lactateHMDB
3-(p-Hydroxyphenyl)-lactateHMDB
3-(p-Hydroxyphenyl)-lactic acidHMDB
a,4-DihydroxybenzenepropanoateHMDB
a,4-Dihydroxybenzenepropanoic acidHMDB
b-(p-Hydroxyphenyl)-DL-lactateHMDB
b-(p-Hydroxyphenyl)-DL-lactic acidHMDB
beta-(p-Hydroxyphenyl)-DL-lactateHMDB
beta-(p-Hydroxyphenyl)-DL-lactic acidHMDB
DL-3-(4-Hydroxyphenyl)lactateHMDB
DL-3-(4-Hydroxyphenyl)lactic acidHMDB
HPLAHMDB
4-Hydroxyphenyllactic acid, (DL)-isomerHMDB
Para-hydroxyphenyllactic acidHMDB
2-HydroxyphloretateHMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acidHMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid HMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
Traditional Namehydroxyphenyllactic acid
CAS Registry Number306-23-0
SMILES
OC(CC1=CC=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
InChI KeyJVGVDSSUAVXRDY-UHFFFAOYSA-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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.9 mg/mL at 16 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.87ALOGPS
logP0.88ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.44 m³·mol⁻¹ChemAxon
Polarizability17.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Epidermis
  • Milk
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000755
DrugBank IDNot Available
Phenol Explorer Compound ID577
FooDB IDFDB017136
KNApSAcK IDC00050491
Chemspider ID9010
KEGG Compound IDC03672
BioCyc ID4-HYDROXYPHENYLLACTATE
BiGG ID2392410
Wikipedia LinkNot Available
METLIN ID5723
PubChem Compound9378
PDB IDNot Available
ChEBI ID17385
References
Synthesis ReferenceDeng, Xi-ling; Wang, Xin-bing; Xiang, Ying; Zhu, Shi-fa. Synthesis of b-(4-hydroxyphenyl)lactic acid. Shihezi Daxue Xuebao, Ziran Kexueban (2005), 23(1), 11-13.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
  3. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]