Human Metabolome Database: Showing metabocard for D-Phenyllactic acid (HMDB0000563)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2018-05-20 09:58:45 UTC

HMDB ID

HMDB0000563

Secondary Accession Numbers

HMDB00563

Metabolite Identification

Common Name

D-Phenyllactic acid

Description

D-Phenyllactic acid, also known as L-3-phenyllactate, 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. D-Phenyllactic acid exists as a solid, slightly soluble (in water), and a weakly acidic compound (based on its pKa). D-Phenyllactic acid has been primarily detected in feces. Within the cell, D-phenyllactic acid is primarily located in the cytoplasm.

Structure

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

Synonyms

Value	Source
ALPHA-HYDROXY-BETA-phenyl-propionIC ACID	ChEBI
L-(-)-3-Phenyllactic acid	ChEBI
L-3-Phenyllactic acid	ChEBI
L-beta-Phenyllactic acid	ChEBI
a-HYDROXY-b-phenyl-propionate	Generator
a-HYDROXY-b-phenyl-propionic acid	Generator
alpha-HYDROXY-beta-phenyl-propionate	Generator
α-hydroxy-β-phenyl-propionate	Generator
α-hydroxy-β-phenyl-propionic acid	Generator
D-Phenyllactate	Generator
L-(-)-3-Phenyllactate	Generator
L-3-Phenyllactate	Generator
L-b-Phenyllactate	Generator
L-b-Phenyllactic acid	Generator
L-beta-Phenyllactate	Generator
L-β-phenyllactate	Generator
L-β-phenyllactic acid	Generator
(+)-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
(2R)-2-Hydroxy-2-phenylpropanoate	HMDB
(2R)-2-Hydroxy-2-phenylpropanoic acid	HMDB
(2R)-2-Hydroxy-2-phenylpropionate	HMDB
(2R)-2-Hydroxy-2-phenylpropionic acid	HMDB
(R)-2-Hydroxy-2-phenylpropionate	HMDB
(R)-2-Hydroxy-2-phenylpropionic acid	HMDB
(R)-2-Phenyl-2-hydroxypropanoate	HMDB
(R)-2-Phenyl-2-hydroxypropanoic acid	HMDB
(R)-3-Phenyl-lactate	HMDB
(R)-3-Phenyl-lactic acid	HMDB
(R)-3-Phenyllactate	HMDB
(R)-3-Phenyllactic acid	HMDB
(R)-a-Hydroxy-3-phenylpropionate	HMDB
(R)-a-Hydroxy-3-phenylpropionic acid	HMDB
(R)-a-Hydroxy-benzenepropanoate	HMDB
(R)-a-Hydroxy-benzenepropanoic acid	HMDB
(R)-alpha-Hydroxy-3-phenylpropionate	HMDB
(R)-alpha-Hydroxy-3-phenylpropionic acid	HMDB
(R)-alpha-Hydroxy-benzenepropanoate	HMDB
(R)-alpha-Hydroxy-benzenepropanoic acid	HMDB
(R)-b-Phenyllactate	HMDB
(R)-b-Phenyllactic acid	HMDB
(R)-beta-Phenyllactate	HMDB
(R)-beta-Phenyllactic acid	HMDB
(R)-Phenyllactate	HMDB
(R)-Phenyllactic acid	HMDB
b-Phenyl-D-lactate	HMDB
b-Phenyl-D-lactic acid	HMDB
beta-Phenyl-delta-lactate	HMDB
beta-Phenyl-delta-lactic acid	HMDB
D-2-Hydroxy-3-phenylpropionate	HMDB
D-2-Hydroxy-3-phenylpropionic acid	HMDB
D-3-Phenyllactate	HMDB
D-3-Phenyllactic acid	HMDB
D-b-Phenyllactate	HMDB
D-b-Phenyllactic acid	HMDB
delta-2-Hydroxy-3-phenylpropionate	HMDB
delta-2-Hydroxy-3-phenylpropionic acid	HMDB
delta-3-Phenyllactate	HMDB
delta-3-Phenyllactic acid	HMDB
delta-beta-Phenyllactate	HMDB
delta-beta-Phenyllactic acid	HMDB
delta-Phenyllactate	HMDB
delta-Phenyllactic acid	HMDB

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

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

Traditional Name

L-3-phenyllactic acid

CAS Registry Number

7326-19-4

SMILES

[H][C@](O)(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-/m0/s1

InChI Key

VOXXWSYKYCBWHO-QMMMGPOBSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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

(2S)-2-hydroxy monocarboxylic acid (CHEBI:43065 )
3-phenyllactic acid (CHEBI:43065 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Feces

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	122-124 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.184	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-c22a5f17e7fecfb666f2	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-c22a5f17e7fecfb666f2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-750e52d0df9e2b90be09	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006x-9540000000-c06e2865c7cf1c780f11	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01bd-2900000000-92cd31ed8e8e8e87180f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-5900000000-d1b1e4fdbfd8306c9265	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-750584951bb8866056f0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-1f4cdc94d5bb4ac6489e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01bc-6900000000-779d8af9b71dee9ffe5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9300000000-bb0139bf3ea8e3c03d20	View in MoNA

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB02494

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05607

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Kamata, Masahiro; Toyomasu, Ryuta; Suzuki, Eiichiro; Tanaka, Takashi. D-Phenyllactic acid production by Brevibacterium or Corynebacterium. Jpn. Kokai Tokkyo Koho (1986), 4 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

D-Phenyllactic acid → (2S)-3-phenyl-2-(sulfooxy)propanoic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

D-Phenyllactic acid → 6-[(1R)-1-carboxy-2-phenylethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
D-Phenyllactic acid → 3,4,5-trihydroxy-6-{[(2S)-2-hydroxy-3-phenylpropanoyl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for D-Phenyllactic acid (HMDB0000563)

Structure for HMDB0000563 (D-Phenyllactic acid)

Enzymes

Reactions

Reactions