ChemFOnt: Showing chemical card for L-3-Phenyllactic acid (CFc000000596)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:01 UTC

Chemfont ID

CFc000000596

Molecule Identification

Common Name

L-3-Phenyllactic acid

Definition

L-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid and then to phenyllactate through the action of lactate dehydrogenase. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-Phenyllactate	ChEBI
D-3-Phenyllactic acid	ChEBI
(R)-3-(Phenyl)lactate	Kegg
(R)-Phenyllactic acid	Generator
D-3-Phenyllactate	Generator
(R)-3-(Phenyl)lactic acid	Generator
L-3-Phenyllactate	Generator
(-)-2-Hydroxy-3-phenylpropanoate	HMDB
(-)-2-Hydroxy-3-phenylpropanoic acid	HMDB
(-)-2-Hydroxy-3-phenylpropionate	HMDB
(-)-2-Hydroxy-3-phenylpropionic acid	HMDB
(-)-3-Phenyllactate	HMDB
(-)-3-Phenyllactic acid	HMDB
(-)-b-Phenyllactate	HMDB
(-)-b-Phenyllactic acid	HMDB
(-)-beta-Phenyllactate	HMDB
(-)-beta-Phenyllactic acid	HMDB
(2S)-2-Hydroxy-3-phenylpropanoate	HMDB
(2S)-2-Hydroxy-3-phenylpropanoic acid	HMDB
(2S)-2-Hydroxy-3-phenylpropionate	HMDB
(2S)-2-Hydroxy-3-phenylpropionic acid	HMDB
(S)-3-Phenyl-lactate	HMDB
(S)-3-Phenyl-lactic acid	HMDB
(S)-3-Phenyllactic acid	HMDB
(S)-a-Hydroxy-benzenepropanoate	HMDB
(S)-a-Hydroxy-benzenepropanoic acid	HMDB
(S)-alpha-Hydroxy-benzenepropanoate	HMDB
(S)-alpha-Hydroxy-benzenepropanoic acid	HMDB
(S)-b-Phenyllactic	HMDB
(S)-beta-Phenyllactic	HMDB
alpha-Hydroxy-beta-phenyl-propionic acid	HMDB
HFA	HMDB
L-(-)-3-Phenyllactic acid	HMDB
L-2-Hydroxy-3-phenyl-propionic acid	HMDB
L-beta-Phenyllactic acid	HMDB
L-Phenyl lactate	HMDB
Phenyllactic acid	HMDB
(R)-3-Phenyllactate	HMDB

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

(2R)-2-hydroxy-3-phenylpropanoic acid

Traditional Name

(R)-phenyllactate

CAS Registry Number

20312-36-1

SMILES

O[C@H](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-/m1/s1

InChI Key

VOXXWSYKYCBWHO-MRVPVSSYSA-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
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

(2R)-2-hydroxy monocarboxylic acid (CHEBI:32978 )
3-phenyllactic acid (CHEBI:32978 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2116554)
Saliva (HMDB: HMDB0000748)

Excreta

Biofluid or Excreta

Feces (PMID: 18085514)
Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0000748)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000748)

Plant

Plant (HMDB: HMDB0000748)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	9.8 g/L	ALOGPS
logP	0.84	ALOGPS
logP	1.18	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	43.46 m³·mol⁻¹	ChemAxon
Polarizability	16.73 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