ChemFOnt: Showing chemical card for Hydroxyphenyllactic acid (CFc000000603)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:02 UTC

Chemfont ID

CFc000000603

Molecule Identification

Common Name

Hydroxyphenyllactic acid

Definition

Hydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID: 4720815 ). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358 ). However, the D-form of hydroxyphenyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358 ). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produce considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754 ). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754 ). Hydroxyphenyllactic acid is a microbial metabolite found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-3-(4-hydroxyphenyl)propanoate	ChEBI
2-Hydroxy-3-(p-hydroxyphenyl)propionic acid	ChEBI
4-Hydroxyphenyllactic acid	ChEBI
beta-(4-Hydroxyphenyl)lactic acid	ChEBI
beta-(p-Hydroxyphenyl)lactic acid	ChEBI
DL-p-Hydroxyphenyllactic acid	ChEBI
p-Hydroxyphenyl lactic acid	ChEBI
4-Hydroxyphenyllactate	Kegg
p-Hydroxyphenyllactate	Kegg
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid	Generator
2-Hydroxy-3-(p-hydroxyphenyl)propionate	Generator
b-(4-Hydroxyphenyl)lactate	Generator
b-(4-Hydroxyphenyl)lactic acid	Generator
beta-(4-Hydroxyphenyl)lactate	Generator
Β-(4-hydroxyphenyl)lactate	Generator
Β-(4-hydroxyphenyl)lactic acid	Generator
b-(p-Hydroxyphenyl)lactate	Generator
b-(p-Hydroxyphenyl)lactic acid	Generator
beta-(p-Hydroxyphenyl)lactate	Generator
Β-(p-hydroxyphenyl)lactate	Generator
Β-(p-hydroxyphenyl)lactic acid	Generator
DL-p-Hydroxyphenyllactate	Generator
p-Hydroxyphenyl lactate	Generator
p-Hydroxyphenyllactic acid	Generator
Hydroxyphenyllactate	Generator
(RS)-3-(4-Hydroxyphenyl)lactate	HMDB
(RS)-3-(4-Hydroxyphenyl)lactic acid	HMDB
3-(4-Hydroxyphenyl)-DL-lactate	HMDB
3-(4-Hydroxyphenyl)-DL-lactic acid	HMDB
3-(4-Hydroxyphenyl)lactate	HMDB
3-(p-Hydroxyphenyl)-lactate	HMDB
3-(p-Hydroxyphenyl)-lactic acid	HMDB
a,4-Dihydroxybenzenepropanoate	HMDB
a,4-Dihydroxybenzenepropanoic acid	HMDB
b-(p-Hydroxyphenyl)-DL-lactate	HMDB
b-(p-Hydroxyphenyl)-DL-lactic acid	HMDB
beta-(p-Hydroxyphenyl)-DL-lactate	HMDB
beta-(p-Hydroxyphenyl)-DL-lactic acid	HMDB
DL-3-(4-Hydroxyphenyl)lactate	HMDB
DL-3-(4-Hydroxyphenyl)lactic acid	HMDB
HPLA	HMDB
4-Hydroxyphenyllactic acid, (DL)-isomer	HMDB
Para-hydroxyphenyllactic acid	HMDB
2-Hydroxyphloretate	HMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid	HMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

2-hydroxy-3-(4-hydroxyphenyl)propanoic acid

Traditional Name

hydroxyphenyllactic acid

CAS Registry Number

306-23-0

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 Key

JVGVDSSUAVXRDY-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:17385 )
2-hydroxy carboxylic acid (CHEBI:17385 )

Functional Ontology

Physiological effect

Health effect

Observation

Supragingival Plaque (HMDB: HMDB0000755)

Respiratory system disorder

Supradiaphragmatic malignancy (HMDB: HMDB0000755)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9106023)
Cerebrospinal Fluid (CSF) (PMID: 10553836)
Saliva (PMID: 22308371)
Cerebrospinal fluid (HMDB: HMDB0000755)

Tissue

Epithelium

Epidermis (HMDB: HMDB0000755)

Organ

Prostate (HMDB: HMDB0000755)
Placenta (HMDB: HMDB0000755)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 19636438)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000755)

Cytoplasm (HMDB: HMDB0000755)
Extracellular (HMDB: HMDB0000755)

Source

Endogenous

Endogenous (HMDB: HMDB0000755)

Plant

Plant (HMDB: HMDB0000755)

Microbe

Microbe (HMDB: HMDB0000755)
Acinetobacter baumannii (HMDB: HMDB0000755)
Klebsiella pneumoniae (HMDB: HMDB0000755)
Pseudomonas aeruginosa (HMDB: HMDB0000755)
Enterococcus faecalis (HMDB: HMDB0000755)
Escherichia coli (HMDB: HMDB0000755)
Lactobacillus (HMDB: HMDB0000755)
Bacteroides fragilis (HMDB: HMDB0000755)
Clostridium (HMDB: HMDB0000755)
Klebsiella (HMDB: HMDB0000755)
Bacteroides thetaiotaomicron (HMDB: HMDB0000755)
Bifidobacteria (HMDB: HMDB0000755)
Bifidobacterium Bifidum (HMDB: HMDB0000755)
Enterococcus faecium (HMDB: HMDB0000755)
Eubacterium lentum (HMDB: HMDB0000755)
Lactobacillus fermentum (HMDB: HMDB0000755)
Staphylococcus (HMDB: HMDB0000755)
Staphylococcus aureus (HMDB: HMDB0000755)

Exogenous

Exogenous (HMDB: HMDB0000755)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Tyrosinemia Type 2 (or Richner-Hanhart Syndrome) (HMDB: HMDB0000755)

Role

Biological role

Human metabolite (HMDB: HMDB0000755)
Bacterial metabolite (HMDB: HMDB0000755)

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00029989)
Phenylketonuria (MarkerDB: MDB00029989)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.79 g/L	ALOGPS
logP	0.87	ALOGPS
logP	0.88	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.44 m³·mol⁻¹	ChemAxon
Polarizability	17.51 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000755

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

4-HYDROXYPHENYLLACTATE

BiGG ID

2392410

Wikipedia Link

Not Available

METLIN ID

5723

PubChem Compound

9378

PDB ID

Not Available

ChEBI ID

17385

Food Biomarker Ontology

Not Available

References

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.

Showing chemical card for Hydroxyphenyllactic acid (CFc000000603)

MOL for CFc000000603 (Hydroxyphenyllactic acid)

3D MOL for CFc000000603 (Hydroxyphenyllactic acid)

3D SDF for CFc000000603 (Hydroxyphenyllactic acid)

3D-SDF for CFc000000603 (Hydroxyphenyllactic acid)

PDB for CFc000000603 (Hydroxyphenyllactic acid)

3D PDB for CFc000000603 (Hydroxyphenyllactic acid)

SMILES for CFc000000603 (Hydroxyphenyllactic acid)

INCHI for CFc000000603 (Hydroxyphenyllactic acid)

Structure for CFc000000603 (Hydroxyphenyllactic acid)

3D Structure for CFc000000603 (Hydroxyphenyllactic acid)