Bovine Metabolome Database: Showing metabocard for Phenyllactic acid (BMDB0000779)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:36:24 UTC

Update Date

2020-06-04 19:53:02 UTC

BMDB ID

BMDB0000779

Secondary Accession Numbers

BMDB00779

Metabolite Identification

Common Name

Phenyllactic acid

Description

Phenyllactic acid, also known as 2-phenyllactate or a-methylmandelate, 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. Based on a literature review a significant number of articles have been published on Phenyllactic acid.

Structure

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

Synonyms

Value	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

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

2-hydroxy-3-phenylpropanoic acid

Traditional Name

β-phenyllactic acid

CAS Registry Number

828-01-3

SMILES

OC(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)

InChI Key

VOXXWSYKYCBWHO-UHFFFAOYSA-N

Chemical Taxonomy

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

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	98 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.83	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0006-2930000000-9c44eea65a6e20c158ee	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-2930000000-9c44eea65a6e20c158ee	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0007-1910000000-1c581a4eacd9a7f2036f	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-cfbc3d9f0107a37ad7f7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00kb-1900000000-e1937415e710a88af8db	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0v4i-4900000000-f7887dfe1f265bcf46ba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0v4i-6900000000-7df2fcf2f9b049e4c39f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0v00-6900000000-992cb5008b3e748b7e66	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-cfbc3d9f0107a37ad7f7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kb-1900000000-a9ac61820c9f5278e2ba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0v4i-4900000000-5e5e2d29a299435f9b35	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0v4i-6900000000-7df2fcf2f9b049e4c39f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0v00-6900000000-992cb5008b3e748b7e66	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0002-0900000000-8940947cbb9a8e6253ee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00si-9600000000-6ba02da72bb3acc762df	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0089-9700000000-901ab7fc4dce05d16406	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-017i-9100000000-248f4ab6119fb2bb911c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-37469cb4526a3ed239e9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01bd-4900000000-f70272565fdcdbdf5209	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9400000000-14afa00d4a96d888572b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-15a50bcc903d54af3f43	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9400000000-0d7b49d15700ae266645	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-ca99933d289067e5347a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0900000000-a96f38f47d5e070f0989	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-1900000000-82f893f2df7cfa6f88eb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f96-9400000000-50e3d4b82e667ef9e4d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-5900000000-eb26ccce038261968168	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-aa44337c740dacf05e9c	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Liver
Mammary Gland
Placenta
Ruminal Fluid

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	8.6 +/- 2.3 uM	Not Specified	Both	Normal	PMID: 10707763	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0142137

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093343

KNApSAcK ID

C00000150

Chemspider ID

1263

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1303

PDB ID

Not Available

ChEBI ID

50392

References

Synthesis Reference

Yu, Jian Ming; Xue, Fen. A method of synthesis of phenyllactic acid and substituted phenyllactic acids. Chinese Chemical Letters (1993), 4(8), 673-4.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Phenyllactic acid (BMDB0000779)

Structure for BMDB0000779 (Phenyllactic acid)