Livestock Metabolome Database: Showing metabocard for Hydroxyphenyllactic acid (LMDB00239)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:25 UTC

Update Date

2016-07-20 21:03:44 UTC

Lmdb

LMDB00239

Secondary Accession Numbers

None

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 hydroxyphneyllactate 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 produced 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 ).

Structure

MOL SDF PDB SMILES InChI

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

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

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

Traditional Name

hydroxyphenyllactic acid

CAS Registry Number

306-23-0

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-004i-1911000000-424dc0a114976e4a6052	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1911000000-424dc0a114976e4a6052	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-b7f0ddb24f5c187d4540	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-3900000000-aece5a68ba54ab74c5ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-003r-5496000000-fbb65d0c963e70625e95	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00li-2900000000-ea59f9dcf58b55bec6ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-054n-9300000000-5b39aa5183630ccd7f4d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0k92-9200000000-c698fdbe1eefac6e9eab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-01qi-0900000000-640a5a477752571a1443	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-03di-0900000000-45b5f23bae1a9641fb0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-01qi-0900000000-640a5a477752571a1443	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-03ei-0900000000-d89828d3625adabd215b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00ou-9000000000-60dd6237cac5c79c7508	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00ri-2900000000-69365cb4d9937f6a96e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00li-1900000000-03a7d2e8f219eba66eee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-029i-0900000000-fd70bef080a1a354df5a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9400000000-65da3c598368dbad66cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-052b-9100000000-6ad54b488ac0183ff4bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9400000000-af41107b1e7be38f765c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-023a994f4d18e32123cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-5900000000-8fcf87adaaae828f3aae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00ri-2900000000-ed974245d122fcbc31c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03ei-1900000000-fd1d5ff4f32cdcdf0a38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00ec-9400000000-9b26dc9e6bb4e1a72cfb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05o9-0900000000-a343595d5c411e940c25	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-0900000000-1f777ab6b9486c181355	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9800000000-db82c9bf8afdb32af6de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-3e1a7023e9214816e8a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-2900000000-c05e995d8c57a180bae7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mx-9800000000-729b43ad9499a14c2d01	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details

External Links

DrugBank ID

Not Available

HMDB ID

FooDB ID

Phenol Explorer ID

KNApSAcK ID

BiGG ID

BioCyc ID

4-HYDROXYPHENYLLACTATE

METLIN ID

5723

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [4720815 ]
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. [3126358 ]
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. [23061754 ]

Showing metabocard for Hydroxyphenyllactic acid (LMDB00239)

Structure for LMDB00239 (Hydroxyphenyllactic acid)