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

Microbial

Plant

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:49:32 UTC

Update Date

2024-10-13 07:45:28 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 SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₉H₁₀O₃

Average Mass

166.1739

Monoisotopic Mass

166.062994186

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	335.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	69.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	372.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	379.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	368.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	344.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1454.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	117.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	540.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	237.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	242.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	199.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	113.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	120.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	399.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	103.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	316.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1034.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	846.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	D-Phenyllactic acid_TMS_1	C[Si](C)(C)O[C@@H](CC1=CC=CC=C1)C(=O)O	standard non polar	2025-10-24	2169.61
Gas Chromatography	D-Phenyllactic acid_TMS_2	C[Si](C)(C)OC(=O)[C@@H](O)CC1=CC=CC=C1	standard non polar	2025-10-24	1892.77
Gas Chromatography	D-Phenyllactic acid_TMS_3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-24	2018.48
Gas Chromatography	D-Phenyllactic acid_TMS_1	C[Si](C)(C)O[C@@H](CC1=CC=CC=C1)C(=O)O	standard polar	2025-10-24	2235.85
Gas Chromatography	D-Phenyllactic acid_TMS_2	C[Si](C)(C)OC(=O)[C@@H](O)CC1=CC=CC=C1	standard polar	2025-10-24	2000.98
Gas Chromatography	D-Phenyllactic acid_TMS_3	C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-24	2370.02

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reference
MMDBr0012748	L-Phenylalanine	Phenylpyruvic acid	Not Available	9687465
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

Reaction ID	Precursor	Product	Enzyme	Reference
MMDBr0012748	L-Phenylalanine	Phenylpyruvic acid	Not Available	9687465
MMDBr0012750	Phenylpyruvic acid	D-Phenyllactic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012755	D-Phenyllactic acid	2-Phenylpropionate	Not Available	Manually annotated by MiMeDB team

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/Eubacteria	Firmicutes	11	Human ; Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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:0x00007f9af09b1cd8>

3D MOL for #<Metabolite:0x00007f9af09b1cd8>

3D SDF for #<Metabolite:0x00007f9af09b1cd8>

3D-SDF for #<Metabolite:0x00007f9af09b1cd8>

PDB for #<Metabolite:0x00007f9af09b1cd8>

3D PDB for #<Metabolite:0x00007f9af09b1cd8>

SMILES for #<Metabolite:0x00007f9af09b1cd8>

INCHI for #<Metabolite:0x00007f9af09b1cd8>

Structure for #<Metabolite:0x00007f9af09b1cd8>

3D Structure for #<Metabolite:0x00007f9af09b1cd8>