Human Metabolome Database: Showing metabocard for Hydroxyphenyllactic acid (HMDB00755)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

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

Record Information

Version

3.6

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2017-07-18 21:41:27 UTC

HMDB ID

HMDB00755

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 3D-SDF PDB SMILES InChI View 3D Structure

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
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid	Generator
Hydroxyphenyllactate	Generator
2-Hydroxy-3-(P-hydroxyphenyl)propionate	Generator
4-Hydroxyphenyllactate	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
(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-(4-Hydroxyphenyl)lactic acid	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	MeSH
Para-hydroxyphenyllactic acid	MeSH
P-Hydroxyphenyllactate	MeSH

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

This compound belongs to the class of chemical entities known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Phenylpropanoids and polyketides

Sub Class

Phenylpropanoic acids

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 and Quantified

Origin

Endogenous

Microbial

Biofunction

Not Available

Application

Not Available

Cellular locations

Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	12.9 mg/mL at 16 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.79 mg/mL	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	1	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 (3 TMS)	splash10-004i-1911000000-424dc0a114976e4a6052	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
GC-MS	GC-MS Spectrum - GC-EI-TOF	splash10-004i-0900000000-b7f0ddb24f5c187d4540	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF	splash10-004i-0900000000-b7f0ddb24f5c187d4540	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00li-2900000000-ea59f9dcf58b55bec6ca	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-054n-9300000000-5b39aa5183630ccd7f4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0k92-9200000000-c698fdbe1eefac6e9eab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-01qi-0900000000-640a5a477752571a1443	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-03di-0900000000-45b5f23bae1a9641fb0b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-03ei-0900000000-d89828d3625adabd215b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

Biological Properties

Cellular Locations

Mitochondria

Biofluid Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Location

Epidermis
Prostate

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.64 +/- 0.24 uM	Adult (>18 years old)	Both	Normal	9106023	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified		Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified		Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified		Children (1-13 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified		Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27065191	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	25.10 +/- 14.93 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.55-1.2 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	5.393 +/- 4.849 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	35.939 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.05 +/- 0.43 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	1.1 (0.2-2.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	3.7 (0.1-11.5) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	4.8 (2.7-5.3) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	0.51-0.94 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	1.6 (0.3-5.8) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.5 (0.1-8.7) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.0 (0.4-7.3) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	<50.12 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	3.2 (1.5-3.9) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.8 (2.6-3.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.80 +/- 0.10 uM	Adult (>18 years old)	Both	Morphine treatment	10553836	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	ICD	19636438	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	ICD	19636438	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	5.879 +/- 5.443 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	8.512 +/- 4.226 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	details
Urine	Detected and Quantified	6.21 +/- 4.38 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	12.6 +/- 36.00 umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	2091926	details

Associated Disorders and Diseases

Disease References

Supradiaphragmatic malignancy
Goudas LC, Langlade A, Serrie A, Matson W, Milbury P, Thurel C, Sandouk P, Carr DB: Acute decreases in cerebrospinal fluid glutathione levels after intracerebroventricular morphine for cancer pain. Anesth Analg. 1999 Nov;89(5):1209-15. [PubMed:10553836 ]
Phenylketonuria
Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]

Associated OMIM IDs

261600 (Phenylketonuria)

External Links

DrugBank ID

Not Available

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

577

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB019021

KNApSAcK ID

Not Available

Chemspider ID

9010

KEGG Compound ID

C03672

BioCyc ID

4-HYDROXYPHENYLLACTATE

BiGG ID

2392410

Wikipedia Link

Not Available

NuGOwiki Link

Metagene Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17385

References

Synthesis Reference

Deng, Xi-ling; Wang, Xin-bing; Xiang, Ying; Zhu, Shi-fa. Synthesis of b-(4-hydroxyphenyl)lactic acid. Shihezi Daxue Xuebao, Ziran Kexueban (2005), 23(1), 11-13.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]
Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
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. [PubMed:1444166 ]
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. [PubMed:1249684 ]
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. [PubMed:3126358 ]
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. [PubMed:9106023 ]
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 ]
Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738 ]
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. [PubMed:6463026 ]
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 ]
(). 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). . . [ISBN:978-0079130358 ]

Showing metabocard for Hydroxyphenyllactic acid (HMDB00755)

Structure for HMDB00755 (Hydroxyphenyllactic acid)