MiMeDB: Showing metabocard for Hydroxyphenyllactic acid (MMDBc0000539)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:04 UTC

Update Date

2024-10-17 03:16:33 UTC

Metabolite ID

MMDBc0000539

Metabolite Identification

Common Name

Hydroxyphenyllactic acid

Description

Hydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID: 4720815 ). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358 ). However, the D-form of hydroxyphenyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358 ). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produce considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754 ). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754 ). Hydroxyphenyllactic acid is a microbial metabolite found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416 ).

Structure

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

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011122D          

 13 13  0  0  1  0            999 V2000
    5.1418   -2.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -0.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5409   -2.0060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619   -3.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -2.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4298   -1.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -1.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -1.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739   -2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -3.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  8  2  0  0  0  0
  3  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000539

> <DATABASE_NAME>
MIME

> <SMILES>
OC(CC1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)

> <INCHI_KEY>
JVGVDSSUAVXRDY-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.508950163763846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.8809315280000001

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.50382828900583

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5839647995095922

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8298154633716104

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
45.439700000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyphenyllactic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0       9.598  -5.297   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.899  -1.449   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.210  -3.745   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.916  -6.068   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.912  -3.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.598  -3.745   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.269  -2.973   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.899  -2.992   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.583  -2.992   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.912  -5.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.245  -5.297   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.245  -3.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.583  -6.068   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4   11                                                            
CONECT    5    7    9   10                                                  
CONECT    6    1    7    8                                                  
CONECT    7    5    6                                                       
CONECT    8    2    3    6                                                  
CONECT    9    5   12                                                       
CONECT   10    5   13                                                       
CONECT   11    4   12   13                                                  
CONECT   12    9   11                                                       
CONECT   13   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
2-Hydroxy-3-(4-hydroxyphenyl)propanoate	ChEBI
2-Hydroxy-3-(p-hydroxyphenyl)propionic acid	ChEBI
4-Hydroxyphenyllactic acid	ChEBI
beta-(4-Hydroxyphenyl)lactic acid	ChEBI
beta-(p-Hydroxyphenyl)lactic acid	ChEBI
DL-p-Hydroxyphenyllactic acid	ChEBI
p-Hydroxyphenyl lactic acid	ChEBI
4-Hydroxyphenyllactate	Kegg
p-Hydroxyphenyllactate	Kegg
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid	Generator
2-Hydroxy-3-(p-hydroxyphenyl)propionate	Generator
b-(4-Hydroxyphenyl)lactate	Generator
b-(4-Hydroxyphenyl)lactic acid	Generator
beta-(4-Hydroxyphenyl)lactate	Generator
Β-(4-hydroxyphenyl)lactate	Generator
Β-(4-hydroxyphenyl)lactic acid	Generator
b-(p-Hydroxyphenyl)lactate	Generator
b-(p-Hydroxyphenyl)lactic acid	Generator
beta-(p-Hydroxyphenyl)lactate	Generator
Β-(p-hydroxyphenyl)lactate	Generator
Β-(p-hydroxyphenyl)lactic acid	Generator
DL-p-Hydroxyphenyllactate	Generator
p-Hydroxyphenyl lactate	Generator
p-Hydroxyphenyllactic acid	Generator
Hydroxyphenyllactate	Generator
(RS)-3-(4-Hydroxyphenyl)lactate	HMDB
(RS)-3-(4-Hydroxyphenyl)lactic acid	HMDB
3-(4-Hydroxyphenyl)-DL-lactate	HMDB
3-(4-Hydroxyphenyl)-DL-lactic acid	HMDB
3-(4-Hydroxyphenyl)lactate	HMDB
3-(p-Hydroxyphenyl)-lactate	HMDB
3-(p-Hydroxyphenyl)-lactic acid	HMDB
a,4-Dihydroxybenzenepropanoate	HMDB
a,4-Dihydroxybenzenepropanoic acid	HMDB
b-(p-Hydroxyphenyl)-DL-lactate	HMDB
b-(p-Hydroxyphenyl)-DL-lactic acid	HMDB
beta-(p-Hydroxyphenyl)-DL-lactate	HMDB
beta-(p-Hydroxyphenyl)-DL-lactic acid	HMDB
DL-3-(4-Hydroxyphenyl)lactate	HMDB
DL-3-(4-Hydroxyphenyl)lactic acid	HMDB
HPLA	HMDB
4-Hydroxyphenyllactic acid, (DL)-isomer	HMDB
Para-hydroxyphenyllactic acid	HMDB
2-Hydroxyphloretate	HMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid	HMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid	HMDB

Molecular Formula

C₉H₁₀O₄

Average Mass

182.1733

Monoisotopic Mass

182.057908808

IUPAC Name

2-hydroxy-3-(4-hydroxyphenyl)propanoic acid

Traditional Name

hydroxyphenyllactic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)

InChI Key

JVGVDSSUAVXRDY-UHFFFAOYSA-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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:17385 )
2-hydroxy carboxylic acid (CHEBI:17385 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.79 g/L	ALOGPS
logP	0.87	ALOGPS
logP	0.88	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.44 m³·mol⁻¹	ChemAxon
Polarizability	17.51 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 - GC-MS (3 TMS)	splash10-004i-1911000000-424dc0a114976e4a6052	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1911000000-424dc0a114976e4a6052	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-b7f0ddb24f5c187d4540	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-3900000000-aece5a68ba54ab74c5ee	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-003r-5496000000-fbb65d0c963e70625e95	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 (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 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_1_3) - 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00li-2900000000-ea59f9dcf58b55bec6ca	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-054n-9300000000-5b39aa5183630ccd7f4d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0k92-9200000000-c698fdbe1eefac6e9eab	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-01qi-0900000000-640a5a477752571a1443	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-03di-0900000000-45b5f23bae1a9641fb0b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-01qi-0900000000-640a5a477752571a1443	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-03ei-0900000000-d89828d3625adabd215b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00ou-9000000000-60dd6237cac5c79c7508	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00ri-2900000000-69365cb4d9937f6a96e0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00li-1900000000-03a7d2e8f219eba66eee	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-029i-0900000000-fd70bef080a1a354df5a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9400000000-65da3c598368dbad66cd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-052b-9100000000-6ad54b488ac0183ff4bf	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9400000000-af41107b1e7be38f765c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-023a994f4d18e32123cd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-5900000000-8fcf87adaaae828f3aae	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00ri-2900000000-ed974245d122fcbc31c0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03ei-1900000000-fd1d5ff4f32cdcdf0a38	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00ec-9400000000-9b26dc9e6bb4e1a72cfb	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05o9-0900000000-a343595d5c411e940c25	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-0900000000-1f777ab6b9486c181355	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9800000000-db82c9bf8afdb32af6de	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-3e1a7023e9214816e8a5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-2900000000-c05e995d8c57a180bae7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mx-9800000000-729b43ad9499a14c2d01	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Placenta
Prostate
Saliva
Urine

Tissue Locations

Epidermis
Placenta
Prostate

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
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000055	4-Hydroxyphenylpyruvic acid	Hydroxyphenyllactic acid	Not Available	VMH; KEGG	11583838 12232327
MMDBr0002191	Hydroxyphenyllactic acid	4-Hydroxycinnamic acid	Not Available	VMH; KEGG	30371894
MMDBr0010414	4-Hydroxyphenylpyruvic acid	Hydroxyphenyllactic acid	Not Available	VMH; KEGG	30371894

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reference
MMDBr0012738	L-Tyrosine	4-Hydroxyphenylpyruvic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012740	4-Hydroxyphenylpyruvic acid	Hydroxyphenyllactic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012743	Hydroxyphenyllactic acid	Desaminotyrosine	Not Available	Manually annotated by MiMeDB team

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Reference
MMDBr0012738	L-Tyrosine	4-Hydroxyphenylpyruvic acid	Not Available		Manually annotated by MiMeDB team
MMDBr0012740	4-Hydroxyphenylpyruvic acid	Hydroxyphenyllactic acid	Not Available		Manually annotated by MiMeDB team
MMDBr0012742	Hydroxyphenyllactic acid	p-Hydroxyphenylacetic acid	Not Available		Manually annotated by MiMeDB team
MMDBr0012733	p-Hydroxyphenylacetic acid	p-Cresol	Not Available		11231288
MMDBr0012735	p-Cresol	p-Cresol sulfate	Sulfotransferase 1A1	conjugation; phase-II biotransformation; sulfate-conjugation	Manually annotated by MiMeDB team

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012770	Hydroxyphenyllactic acid	4-Hydroxycinnamic acid	Not Available			19961416
MMDBr0012805	4-Vinylphenol	4-Ethylphenol	Not Available	vinyl phenol reductase

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Phenylketonuria		Association	Human Urine	HMDB	2091926
Phenylketonuria	Increased	Association	Human Urine	HMDB	4837567
Eosinophilic esophagitis	Decreased	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Schizophrenia	increased	Association	Human urine	PubMed	30295550
Huntington's disease	decreased	Association	Human plasma	PubMed	26273688
Ros production	impairs			HMDB	2306175

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	3	Human stool; Human ; Human feces; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	4	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Cow	FooDB	Not Available

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	12.6	36			umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	HMDB	2091926
Human Urine	Detected and Quantified	1.1		0.2	2.6	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected and Quantified	33.513	76.957			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	74.474	94.334			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	139.639	122.882			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	22.342	30.41			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	17.377	21.101			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	75.0948	98.678			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	4.8		2.7	5.3	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	3.7		0.1	11.5	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	1		0.4	7.3	umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	1.6		0.3	5.8	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	1.5		0.1	8.7	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Blood	Detected and Quantified	0.64	0.24			uM	Adult (>18 years old)	Both	Normal	HMDB	9106023
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.8	0.1			uM	Adult (>18 years old)	Both	Morphine treatment	HMDB	10553836
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	CCD	HMDB	19636438
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ileal Crohn's disease	HMDB	19636438
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Urine	Detected and Quantified	2.8		2.6	3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	3.2		1.5	3.9	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified						Infant (0-1 year old)	NULL	Normal	HMDB	24628373
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	Colorectal cancer	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26269369
Human Urine	Detected and Quantified			0.55	1.2	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.51	0.94	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human Blood	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	27355821
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	29808030
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Supragingival Plaque	HMDB	31026179
Human Urine	Detected and Quantified			0	1	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	2	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	1	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	2.3	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27065191
Human Saliva	Detected and Quantified	25.1	14.93			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Urine	Detected and Quantified	5.393	4.849			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.879	5.443			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	8.512	4.226			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	35.939				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	6.21	4.38			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	1.05	0.43			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	12.6	36.00			umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	HMDB	2091926
Human Urine	Detected and Quantified	139.639	122.882			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	74.474	94.334			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	75.0948	98.678			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified			0	1.0	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	1.0	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	2	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	2.3	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0.51	0.94	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.55	1.2	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Blood	Detected and Quantified	0.64	0.24			uM	Adult (>18 years old)	Both	Normal	HMDB	9106023
Human Urine	Detected and Quantified	1.0		0.4	7.3	umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	1.1		0.2	2.6	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected and Quantified	1.5		0.1	8.7	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	1.6		0.3	5.8	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	17.377	21.101			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	2.8		2.6	3.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	22.342	30.410			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	3.2		1.5	3.9	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	3.7		0.1	11.5	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	33.513	76.957			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	4.8		2.7	5.3	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	5.879	5.443			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	6.21	4.38			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	35.939				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.393	4.849			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	<50.12				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified	1.05	0.43			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	25.10	14.93			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Infant (0-1 year old)	NULL	Normal	HMDB	24628373
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27065191
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26269369
Human Blood	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	27355821
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
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000755

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

4-HYDROXYPHENYLLACTATE

BiGG ID

2392410

Wikipedia Link

Not Available

METLIN ID

5723

PubChem Compound

9378

PDB ID

Not Available

ChEBI ID

17385

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Roth K, Cohn R, Yandrasitz J, Preti G, Dodd P, Segal S: Beta-methylcrotonic aciduria associated with lactic acidosis. J Pediatr. 1976 Feb;88(2):229-35. doi: 10.1016/s0022-3476(76)80987-0. [PubMed:1249684 ]
Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. doi: 10.1177/000456329202900509. [PubMed:1444166 ]
Spaapen LJ, Ketting D, Wadman SK, Bruinvis L, Duran M: Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin. J Inherit Metab Dis. 1987;10(4):383-90. doi: 10.1007/BF01799981. [PubMed:3126358 ]
Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. doi: 10.1016/0003-2697(86)90497-5. [PubMed:3706738 ]
Mrochek JE, Dinsmore SR, Ohrt DW: Monitoring phenylalanine-tyrosine metabolism by high-resolution liquid chromatography of urine. Clin Chem. 1973 Aug;19(8):927-36. [PubMed:4720815 ]
Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
Jakobs C, Sweetman L, Nyhan WL: Chemical analysis of succinylacetone and 4-hydroxyphenyllactate in amniotic fluid using selective ion monitoring. Prenat Diagn. 1984 May-Jun;4(3):187-94. doi: 10.1002/pd.1970040305. [PubMed:6463026 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. doi: 10.1016/s0378-4347(96)00411-2. [PubMed:9106023 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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 ]
Beloborodova N, Bairamov I, Olenin A, Shubina V, Teplova V, Fedotcheva N: Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils. J Biomed Sci. 2012 Oct 12;19:89. doi: 10.1186/1423-0127-19-89. [PubMed:23061754 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Charles Scriver, Arthur Beaudet, William Sly, David Valle, Barton Childs, Kenneth Kinzler, Bert Vogelstein (2000). Charles Scriver, Arthur Beaudet, William Sly, David Valle, Barton Childs, Kenneth Kinzler, Bert Vogelstein. The Metabolic and Molecular Bases of Inherited Disease. McGraw-Hill Professional; 8 edition (Dec 15 2000). . McGraw-Hill Professional.

Showing metabocard for Hydroxyphenyllactic acid (MMDBc0000539)

MOL for #<Metabolite:0x0000556b6ab6f4b0>

3D MOL for #<Metabolite:0x0000556b6ab6f4b0>

3D SDF for #<Metabolite:0x0000556b6ab6f4b0>

3D-SDF for #<Metabolite:0x0000556b6ab6f4b0>

PDB for #<Metabolite:0x0000556b6ab6f4b0>

3D PDB for #<Metabolite:0x0000556b6ab6f4b0>

SMILES for #<Metabolite:0x0000556b6ab6f4b0>

INCHI for #<Metabolite:0x0000556b6ab6f4b0>

Structure for #<Metabolite:0x0000556b6ab6f4b0>

3D Structure for #<Metabolite:0x0000556b6ab6f4b0>