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Identification
YMDB IDYMDB00457
Name3-(4-hydroxyphenyl)lactic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionHydroxyphenyllactic 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. Hydroxyphenyllactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxyphenyllactic acid exists in all eukaryotes, ranging from yeast to humans. Hydroxyphenyllactic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (RS)-3-(4-Hydroxyphenyl)lactate
  • (RS)-3-(4-Hydroxyphenyl)lactic acid
  • 2-Hydroxy-3-(4-hydroxyphenyl)propanoate
  • 2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid
  • 2-Hydroxy-3-(p-hydroxyphenyl)propionate
  • 2-Hydroxy-3-(p-hydroxyphenyl)propionic acid
  • 3-(4-Hydroxyphenyl)-DL-lactate
  • 3-(4-Hydroxyphenyl)-DL-lactic acid
  • 3-(4-Hydroxyphenyl)lactate
  • 3-(4-Hydroxyphenyl)lactic acid
  • 3-(p-hydroxyphenyl)-Lactate
  • 3-(p-hydroxyphenyl)-Lactic acid
  • 4-Hydroxyphenyllactate
  • 4-Hydroxyphenyllactic acid
  • a,4-Dihydroxybenzenepropanoate
  • a,4-Dihydroxybenzenepropanoic acid
  • b-(4-Hydroxyphenyl)lactate
  • b-(4-Hydroxyphenyl)lactic acid
  • b-(p-Hydroxyphenyl)-DL-lactate
  • b-(p-Hydroxyphenyl)-DL-lactic acid
  • b-(p-Hydroxyphenyl)lactate
  • b-(p-Hydroxyphenyl)lactic acid
  • Benzenepropanoic acid, .alpha.,4-dihydroxy-
  • beta-(4-Hydroxyphenyl)lactate
  • beta-(4-Hydroxyphenyl)lactic acid
  • beta-(p-Hydroxyphenyl)-DL-lactate
  • beta-(p-Hydroxyphenyl)-DL-lactic acid
  • beta-(p-Hydroxyphenyl)lactate
  • beta-(p-Hydroxyphenyl)lactic acid
  • DL-3-(4-Hydroxyphenyl)lactate
  • DL-3-(4-Hydroxyphenyl)lactic acid
  • DL-p-Hydroxyphenyllactate
  • DL-p-Hydroxyphenyllactic acid
  • HPLA
  • Hydroxyphenyllactate
  • Lactic acid, (p-hydroxyphenyl)-
  • Lactic acid, 3-(p-hydroxyphenyl)-
  • p-Hydroxyphenyl lactic acid
  • p-Hydroxyphenyllactate
  • Β-(4-hydroxyphenyl)lactate
  • Β-(4-hydroxyphenyl)lactic acid
  • Β-(p-hydroxyphenyl)lactate
  • Β-(p-hydroxyphenyl)lactic acid
  • p-Hydroxyphenyl lactate
  • p-Hydroxyphenyllactic acid
  • 4-Hydroxyphenyllactic acid, (DL)-isomer
  • Para-hydroxyphenyllactic acid
CAS number306-23-0
WeightAverage: 182.1733
Monoisotopic: 182.057908808
InChI KeyJVGVDSSUAVXRDY-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
Traditional IUPAC Namehydroxyphenyllactic acid
Chemical FormulaC9H10O4
SMILESOC(CC1=CC=C(O)C=C1)C(O)=O
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility12.9 mg/mL at 16 oC [BEILSTEIN]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.79 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Tyrosine metabolismPW002441 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Tyrosine metabolismec00350 Map00350
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB ReactionsNot Available
KEGG Reactions
NADH + (4-hydroxyphenyl)pyruvic acid + hydronNAD + 3-(4-hydroxyphenyl)lactic acid
3-(4-hydroxyphenyl)lactic acidwater + trans-4-Coumaric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Deng, 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.
External Links:
ResourceLink
CHEBI ID17385
HMDB IDHMDB00755
Pubchem Compound ID9378
Kegg IDC03672
ChemSpider ID9010
FOODB IDFDB017136
Wikipedia IDNot Available
BioCyc IDCPD-6978