MiMeDB: Showing metabocard for D-Phenyllactic acid (MMDBc0048006)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:49:32 UTC

Update Date

2022-09-01 02:13:51 UTC

Metabolite ID

MMDBc0048006

Metabolite Identification

Common Name

D-Phenyllactic acid

Description

Phenyllactic acid is a product of phenylalanine catabolism. An elevated level of phenyllactic acid is found in body fluids of patients with or phenylketonuria.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HFA                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0      -0.294   2.290   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.040   1.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.373   2.290   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.373   3.830   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.040  -0.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.294  -0.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.294  -2.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.628  -0.020   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.628  -3.100   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.961  -0.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.961  -2.330   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.707   1.520   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       1.040   2.610   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    5   13                                             
CONECT    3    2    4   12                                                  
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    3                                                            
CONECT   13    2                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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
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
D-Phenyllactate	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
(S)-3-Phenyllactate	HMDB

Molecular Formula

C₉H₁₀O₃

Average Mass

166.1739

Monoisotopic Mass

166.062994186

IUPAC Name

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

Traditional Name

L-3-phenyllactic acid

CAS Registry Number

Not Available

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

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

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-c22a5f17e7fecfb666f2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-c22a5f17e7fecfb666f2	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-750e52d0df9e2b90be09	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006x-9540000000-c06e2865c7cf1c780f11	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0gb9-1900000000-cc48c5ff57b37ce10c09	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01bd-2900000000-92cd31ed8e8e8e87180f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-5900000000-d1b1e4fdbfd8306c9265	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-750584951bb8866056f0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-1f4cdc94d5bb4ac6489e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01bc-6900000000-779d8af9b71dee9ffe5a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9300000000-bb0139bf3ea8e3c03d20	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-5900000000-eb26ccce038261968168	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-aa44337c740dacf05e9c	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-6509f4478fff1766b65a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3900000000-15a50bcc903d54af3f43	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9400000000-0d7b49d15700ae266645	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-ca99933d289067e5347a	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192023	Sulfotransferase family cytosolic 2B member 1	Enzyme	O00204	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012750	Phenylpyruvic acid	D-Phenyllactic acid	Not Available			Manually annotated by MiMeDB team
MMDBr0012754	D-Phenyllactic acid	Phenylacetic acid	Not Available			Manually annotated by MiMeDB team
MMDBr0012755	D-Phenyllactic acid	2-Phenylpropionate	Not Available			Manually annotated by MiMeDB team
MMDBr0008222	NAD	Hydrogen Ion	Not Available	Phenyllactate oxidoreductase	VMH	30371894
MMDBr0012771	D-Phenyllactic acid	trans-Cinnamic acid	Not Available		PMID: 19961416	19961416

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human saliva	PubMed	28453477

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	11	Human ; Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food	Beer	Barley	PubMed	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	18085514
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000563

DrugBank ID

DB02494

Phenol Explorer Compound ID

Not Available

FooDB 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

5547

PubChem Compound

444718

PDB ID

Not Available

ChEBI ID

43065

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Beloborodova NV, Khodakova AS, Bairamov IT, Olenin AY: Microbial origin of phenylcarboxylic acids in the human body. Biochemistry (Mosc). 2009 Dec;74(12):1350-5. doi: 10.1134/s0006297909120086. [PubMed:19961416 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for D-Phenyllactic acid (MMDBc0048006)

MOL for #<Metabolite:0x00007fa4da63c5c8>

3D MOL for #<Metabolite:0x00007fa4da63c5c8>

3D SDF for #<Metabolite:0x00007fa4da63c5c8>

3D-SDF for #<Metabolite:0x00007fa4da63c5c8>

PDB for #<Metabolite:0x00007fa4da63c5c8>

3D PDB for #<Metabolite:0x00007fa4da63c5c8>

SMILES for #<Metabolite:0x00007fa4da63c5c8>

INCHI for #<Metabolite:0x00007fa4da63c5c8>

Structure for #<Metabolite:0x00007fa4da63c5c8>

3D Structure for #<Metabolite:0x00007fa4da63c5c8>