Showing Compound Phenyllactic acid (FDB022236)

Record Information

Version

1.0

Creation date

2011-09-21 00:10:41 UTC

Update date

2015-10-09 22:30:16 UTC

Primary ID

FDB022236

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phenyllactic acid

Description

Phenyllactic acid a product of phenylalanine catabolism, appearing prominently in the urine in individuals with phenylketonuria. Levels of several phenylalanine metabolites, including phenylacetate (PAA), phenyllactate (PLA), and phenylpyruvate (PPA)) are elevated in Phenylketonuria (PKU) (OMIM 261600). Phenyllactic acid 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. PMID: 10790306; OMIM: 261600 [HMDB]

CAS Number

828-01-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
2-Hydroxy-2-phenylpropionic acid	ChEBI
2-Phenyllactic acid	ChEBI
alpha-Hydroxy-alpha-methylbenzeneacetic acid	ChEBI
alpha-Hydroxy-alpha-phenylpropionic acid	ChEBI
alpha-Methylmandelic acid	ChEBI
2-Hydroxy-2-phenylpropionate	Generator
2-Phenyllactate	Generator
a-Hydroxy-a-methylbenzeneacetate	Generator
a-Hydroxy-a-methylbenzeneacetic acid	Generator
alpha-Hydroxy-alpha-methylbenzeneacetate	Generator
Α-hydroxy-α-methylbenzeneacetate	Generator
Α-hydroxy-α-methylbenzeneacetic acid	Generator
a-Hydroxy-a-phenylpropionate	Generator
a-Hydroxy-a-phenylpropionic acid	Generator
alpha-Hydroxy-alpha-phenylpropionate	Generator
Α-hydroxy-α-phenylpropionate	Generator
Α-hydroxy-α-phenylpropionic acid	Generator
a-Methylmandelate	Generator
a-Methylmandelic acid	Generator
alpha-Methylmandelate	Generator
Α-methylmandelate	Generator
Α-methylmandelic acid	Generator
Phenyllactate	Generator
Atrolactic acid, (+-)-isomer	MeSH
Hydroxyphenylpropionic acid	MeSH
Atrolactic acid	MeSH
Atrolactic acid monosodium salt, (S)-isomer	MeSH
HMMA	MeSH
Hydroxymethylmandelic acid	MeSH
2-Hydroxy-3-phenylpropionic acid	ChEBI
beta-Phenyllactic acid	ChEBI
DL-3-Phenyllactic acid	ChEBI
DL-beta-Phenyllactic acid	ChEBI
2-Hydroxy-3-phenylpropionate	Generator
b-Phenyllactate	Generator
b-Phenyllactic acid	Generator
beta-Phenyllactate	Generator
β-phenyllactate	Generator
β-phenyllactic acid	Generator
DL-3-Phenyllactate	Generator
DL-b-Phenyllactate	Generator
DL-b-Phenyllactic acid	Generator
DL-beta-Phenyllactate	Generator
DL-β-phenyllactate	Generator
DL-β-phenyllactic acid	Generator
3-Phenyllactic acid	MeSH, HMDB
3-Phenyllactic acid, monosodium salt	MeSH, HMDB
3-Phenyllactate	MeSH, Generator, HMDB
3-Phenyllactic acid, calcium salt	MeSH, HMDB
3-Phenyllactic acid, (D)-isomer	MeSH, HMDB
3-Phenyllactic acid, (DL)-isomer	MeSH, HMDB
3-Phenyllactic acid, (L)-isomer	MeSH, HMDB
2-Hydroxy-3-(phenyl)propanoic acid	HMDB
3-(Phenyl)-2-hydroxypropanoic acid	HMDB
2-Hydroxy-3-phenylpropanoate	hmdb
2-Hydroxy-3-phenylpropanoic acid	hmdb
3-Phenyl-2-hydroxypropanoate	hmdb
3-Phenyl-2-hydroxypropanoic acid	hmdb
a-Hydroxybenzenepropanoate	hmdb
a-Hydroxybenzenepropanoic acid	hmdb
alpha-Hydroxybenzenepropanoate	hmdb
alpha-Hydroxybenzenepropanoic acid	hmdb
DL-2-Hydroxy-3-phenylpropionate	hmdb
DL-2-Hydroxy-3-phenylpropionic acid	hmdb

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	16.7 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

Chemical Formula

C9H10O3

IUPAC name

2-hydroxy-3-phenylpropanoic acid

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)

InChI Key

VOXXWSYKYCBWHO-UHFFFAOYSA-N

Isomeric SMILES

OC(CC1=CC=CC=C1)C(O)=O

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

Classification

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Hydroxy acid
Monocyclic benzene moiety
Alpha-hydroxy acid
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

2-hydroxy monocarboxylic acid (CHEBI:50392 )

Ontology

Biofluid and excreta:

Whole grain cereal products

Nuts and legumes:

Nuts

Legumes:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Phenyllactic acid, 2 TMS, GC-MS Spectrum	splash10-0006-2930000000-9c44eea65a6e20c158ee	Spectrum
GC-MS	Phenyllactic acid, non-derivatized, GC-MS Spectrum	splash10-0006-2930000000-9c44eea65a6e20c158ee	Spectrum
GC-MS	Phenyllactic acid, non-derivatized, GC-MS Spectrum	splash10-0007-1910000000-1c581a4eacd9a7f2036f	Spectrum
Predicted GC-MS	Phenyllactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9300000000-750e52d0df9e2b90be09	Spectrum
Predicted GC-MS	Phenyllactic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9540000000-c06e2865c7cf1c780f11	Spectrum
Predicted GC-MS	Phenyllactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenyllactic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenyllactic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenyllactic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenyllactic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenyllactic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-cfbc3d9f0107a37ad7f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00kb-1900000000-e1937415e710a88af8db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0v4i-4900000000-f7887dfe1f265bcf46ba	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0v4i-6900000000-7df2fcf2f9b049e4c39f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0v00-6900000000-992cb5008b3e748b7e66	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-cfbc3d9f0107a37ad7f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kb-1900000000-a9ac61820c9f5278e2ba	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0v4i-4900000000-5e5e2d29a299435f9b35	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0v4i-6900000000-7df2fcf2f9b049e4c39f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0v00-6900000000-992cb5008b3e748b7e66	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0002-0900000000-8940947cbb9a8e6253ee	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00si-9600000000-6ba02da72bb3acc762df	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0089-9700000000-901ab7fc4dce05d16406	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-017i-9100000000-248f4ab6119fb2bb911c	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-37469cb4526a3ed239e9	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01bd-4900000000-f70272565fdcdbdf5209	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9400000000-14afa00d4a96d888572b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-15a50bcc903d54af3f43	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9400000000-0d7b49d15700ae266645	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-ca99933d289067e5347a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0900000000-a96f38f47d5e070f0989	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-1900000000-82f893f2df7cfa6f88eb	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f96-9400000000-50e3d4b82e667ef9e4d1	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-5900000000-eb26ccce038261968168	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-aa44337c740dacf05e9c	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum