Human Metabolome Database: Showing metabocard for ortho-Hydroxyphenylacetic acid (HMDB0000669)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-02-26 21:22:28 UTC

HMDB ID

HMDB0000669

Secondary Accession Numbers

HMDB00669

Metabolite Identification

Common Name

ortho-Hydroxyphenylacetic acid

Description

ortho-Hydroxyphenylacetic acid, also known as (o-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(Hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. ortho-Hydroxyphenylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). ortho-Hydroxyphenylacetic acid can be found in a number of food items such as natal plum, lemon verbena, half-highbush blueberry, and parsley, which makes ortho-hydroxyphenylacetic acid a potential biomarker for the consumption of these food products. ortho-Hydroxyphenylacetic acid can be found primarily in blood, feces, and urine. Moreover, ortho-hydroxyphenylacetic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism. ortho-Hydroxyphenylacetic acid is a substrate of the enzyme oxidoreductases (EC 1.14.13.-) in the pathway styrene degradation (KEGG). ortho-Hydroxyphenylacetic acid is also a microbial metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(O-Hydroxyphenyl)acetic acid	ChEBI
2'-Hydroxyphenylacetic acid	ChEBI
2-Hydroxybenzeneacetic acid	ChEBI
2-Hydroxyphenylacetic acid	ChEBI
O-Hydroxyphenylacetic acid	ChEBI
(O-Hydroxyphenyl)acetate	Generator
2'-Hydroxyphenylacetate	Generator
2-Hydroxybenzeneacetate	Generator
2-Hydroxyphenylacetate	Generator
O-Hydroxyphenylacetate	Generator
Ortho-hydroxyphenylacetate	Generator
(2-Hydroxyphenyl)acetate	HMDB
(2-Hydroxyphenyl)acetic acid	HMDB
(O-Hydroxyphenyl)-acetate	HMDB
(O-Hydroxyphenyl)-acetic acid	HMDB
2-HPAA	HMDB
Hydroxyphenylacetate	HMDB
Hydroxyphenylacetic acid	HMDB
O-Hydroxyphenyl acetic acid	HMDB
Ortho-hydroxyphenylacetic acid	MeSH

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

2-(2-hydroxyphenyl)acetic acid

Traditional Name

o-hydroxyphenylacetic acid

CAS Registry Number

614-75-5

SMILES

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

InChI Identifier

InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)

InChI Key

CCVYRRGZDBSHFU-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetic acids

Direct Parent

2(hydroxyphenyl)acetic acids

Alternative Parents

Substituents

2(hydroxyphenyl)acetic acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:28478 )
hydroxy monocarboxylic acid (CHEBI:28478 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Plant:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	145 - 147 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	44 mg/mL	Not Available
LogP	0.85	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	6.38 g/L	ALOGPS
logP	0.99	ALOGPS
logP	1.31	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-6	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	2	ChemAxon
Refractivity	39.35 m³·mol⁻¹	ChemAxon
Polarizability	14.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0920000000-ca3851c9928227913a97	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0w29-1970000000-de8569a7d279b97680a4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0960000000-1018d2254ff44190f41a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-ca3851c9928227913a97	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0w29-1970000000-de8569a7d279b97680a4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-0a090cff04cd89d36022	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-6930000000-1903392fd44f061e93eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0900000000-c0378212353f9c247060	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0900000000-2e1d10888e4b882683d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-1900000000-87d962f7cd6aa06c4832	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0900000000-e7c99cfd03a6c025cf2c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0900000000-e7c99cfd03a6c025cf2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-6a2b0b911cb357174c27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-06436376438e44718bb7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9300000000-19f4bd2f314d6c0b49bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-c00a2e1956529eb24b43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pc0-0900000000-a60511b0d00662895871	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-4900000000-68a51d2b15b093ce1545	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.287 +/- 0.033 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.213 +/- 0.021 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.265 +/- 0.032 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.329 +/- 0.064 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.228 +/- 0.019 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.207 +/- 0.023 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.213 +/- 0.026 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	2.281 +/- 2.091 uM	Adult (>18 years old)	Male	Normal	19812218	details
Feces	Detected but not Quantified		Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	21330412	details
Feces	Detected but not Quantified		Adult (>18 years old)	Female	Normal	26709303	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.76 +/- 0.457 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	0.38-0.72 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	22.48 +/- 16.25 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	9656160	details
Urine	Detected and Quantified	0.36-0.53 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 953	12771321	details
Urine	Detected and Quantified	<20 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0.594 +/- 0.372 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	0.966 +/- 1.338 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	1.189 +/- 0.966 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	2.0 (0.9-4.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	7.71 +/- 3.65 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	9656160	details
Urine	Detected and Quantified	2.9 (1.4-3.7) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Irritable bowel syndrome	21330412	details
Urine	Detected and Quantified	0.643 +/- 0.815 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	0.603 +/- 0.339 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	details
Urine	Detected and Quantified	1.226 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	151.592 +/- 98.0886 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	48.301 +/- 20.0636 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	97.346 +/- 59.448 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	36.53 +/- 39.59 umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	2091926	details

Associated Disorders and Diseases

Disease References

Irritable bowel syndrome
Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
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 ] Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

261600 (Phenylketonuria)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012331

KNApSAcK ID

Not Available

Chemspider ID

11476

KEGG Compound ID

C05852

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5639

PubChem Compound

11970

PDB ID

Not Available

ChEBI ID

28478

Food Biomarker Ontology

Not Available

VMH ID

2HYOXPLAC

References

Synthesis Reference

Levine, Joseph; Eble, T. E.; Fischbach, Henry. Preparation of o-hydroxyphenylacetic acid. Journal of the American Chemical Society (1948), 70 1930.

Material Safety Data Sheet (MSDS)

Not Available

General References

Greenslade D, Havler ME, Humphrey MJ, Jordan BJ, Rance MJ: Species differences in the metabolism and excretion of fenclofenac. Xenobiotica. 1980 Oct;10(10):753-60. [PubMed:7456491 ]
Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. [PubMed:357810 ]
Langenbeck U, Behbehani A, Mench-Hoinowski A, Petersen M: Absence of a significant renal threshold for two aromatic acids in phenylketonuric children over two years of age. Eur J Pediatr. 1980 Aug;134(2):115-8. [PubMed:7439195 ]
Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]

Enzymes

Enzyme Details

1. 4-hydroxyphenylpyruvate dioxygenase

General function:: Involved in 4-hydroxyphenylpyruvate dioxygenase activity
Specific function:: Key enzyme in the degradation of tyrosine.
Gene Name:: HPD
Uniprot ID:: P32754
Molecular weight:: 40497.105

Reactions

Phenylpyruvic acid + Oxygen → ortho-Hydroxyphenylacetic acid + Carbon dioxide	details

Showing metabocard for ortho-Hydroxyphenylacetic acid (HMDB0000669)

Structure for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

Enzymes

Reactions