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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

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:05 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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

Physiological effect

Adverse health effect

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis (PMID: 17334708 , PMID: 32966057 , PMID: 22623390 , +128

Source	Link
Pubmed	PMID: 17334708
Pubmed	PMID: 32966057
Pubmed	PMID: 22623390
Pubmed	PMID: 16870009
Pubmed	PMID: 26910390
Pubmed	PMID: 8087979
Pubmed	PMID: 25105552
Pubmed	PMID: 17349089
Pubmed	PMID: 24023812
Pubmed	PMID: 12376931
Pubmed	PMID: 15992788
Pubmed	PMID: 24341803
Pubmed	PMID: 19468821
Pubmed	PMID: 9625050
Pubmed	PMID: 2420598
Pubmed	PMID: 27012787
Pubmed	PMID: 30830347
Pubmed	PMID: 19551947
Pubmed	PMID: 19309105
Pubmed	PMID: 2026685
Pubmed	PMID: 5727921
Pubmed	PMID: 22024767
Pubmed	PMID: 17031479
Pubmed	PMID: 9439441
Pubmed	PMID: 9625050
Pubmed	PMID: 28649521
Pubmed	PMID: 28649521
Pubmed	PMID: 12097436
Pubmed	PMID: 8257730
Pubmed	PMID: 3168222
Pubmed	PMID: 9869364
Pubmed	PMID: 3436096
Pubmed	PMID: 22157537
Pubmed	PMID: 1246461
Pubmed	PMID: 25691415
Pubmed	PMID: 18004736
Pubmed	PMID: 31506554
Pubmed	PMID: 20423563
Pubmed	PMID: 25536744
Pubmed	PMID: 21388201
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 14967154
Pubmed	PMID: 6774165
Pubmed	PMID: 21389975
Pubmed	PMID: 3709568
Pubmed	PMID: 8311084
Pubmed	PMID: 2242313
Pubmed	PMID: 20549362
Pubmed	PMID: 12555941
Pubmed	PMID: 10731506
Pubmed	PMID: 28157703
Pubmed	PMID: 20576202
Pubmed	PMID: 12368406
Pubmed	PMID: 26066683
Pubmed	PMID: 16736096
Pubmed	PMID: 25597510
Pubmed	PMID: 22800120
Pubmed	PMID: 16139832
Pubmed	PMID: 17287286
Pubmed	PMID: 17301081
Pubmed	PMID: 30817767
Pubmed	PMID: 25851806
Pubmed	PMID: 2587127
Pubmed	PMID: 11893004
Pubmed	PMID: 10102904
Pubmed	PMID: 23430553
Pubmed	PMID: 12705346
Pubmed	PMID: 19075476
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 31963255
Pubmed	PMID: 23093139
Pubmed	PMID: 22284503
Pubmed	PMID: 8503438
Pubmed	PMID: 1246461
Pubmed	PMID: 20502474
Pubmed	PMID: 15558695
Pubmed	PMID: 422265
Pubmed	PMID: 22308371
Pubmed	PMID: 20549362
Pubmed	PMID: 9177981
Pubmed	PMID: 16828325
Pubmed	PMID: 16460720
Pubmed	PMID: 28157703
Pubmed	PMID: 8487492
Pubmed	PMID: 23890588
Pubmed	PMID: 14586528
Pubmed	PMID: 12927681
Pubmed	PMID: 9686366
Pubmed	PMID: 9029640
Pubmed	PMID: 22148915
Pubmed	PMID: 27123458
Pubmed	PMID: 20971021
Pubmed	PMID: 3169394
Pubmed	PMID: 21670092
Pubmed	PMID: 23363473
Pubmed	PMID: 15519880
Pubmed	PMID: 2380628
Pubmed	PMID: 6616873
Pubmed	PMID: 1870421
Pubmed	PMID: 19754154
Pubmed	PMID: 9857238
Pubmed	PMID: 12771321
Pubmed	PMID: 2702744
Pubmed	PMID: 9554495
Pubmed	PMID: 19033659
Pubmed	PMID: 19033659
Pubmed	PMID: 22887155
Pubmed	PMID: 17474139
Pubmed	PMID: 18953024
Pubmed	PMID: 6774165
Pubmed	PMID: 11052553
Pubmed	PMID: 16939360
Pubmed	PMID: 22827565
Pubmed	PMID: 21736852
Pubmed	PMID: 12661026
Pubmed	PMID: 18818040
Pubmed	PMID: 23770102
Pubmed	PMID: 15651030
Pubmed	PMID: 11307586
Pubmed	PMID: 21389975
Pubmed	PMID: 1640293
Pubmed	PMID: 25712379
Pubmed	PMID: 23770102
Pubmed	PMID: 24390407
Pubmed	PMID: 26709303
Pubmed	PMID: 3354621
Pubmed	PMID: 29030856
Pubmed	PMID: 12706375
Pubmed	PMID: 9869358

)

Genetic disorder

Inborn errors of metabolism

Phenylketonuria - Concentration is elevated compared to control group (PMID: 24023812 , PMID: 6321058 , PMID: 20971021 , +55

Source	Link
Pubmed	PMID: 24023812
Pubmed	PMID: 6321058
Pubmed	PMID: 20971021
Pubmed	PMID: 20573794
Pubmed	PMID: 23657156
Pubmed	PMID: 22800120
Pubmed	PMID: 21389975
Pubmed	PMID: 27012787
Pubmed	PMID: 9625050
Pubmed	PMID: 15740018
Pubmed	PMID: 12663291
Pubmed	PMID: 2702744
Pubmed	PMID: 16939360
Pubmed	PMID: 17474139
Pubmed	PMID: 15992788
Pubmed	PMID: 22827565
Pubmed	PMID: 22148915
Pubmed	PMID: 21388201
Pubmed	PMID: 22932811
Pubmed	PMID: 19551947
Pubmed	PMID: 31775291
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 19033659
Pubmed	PMID: 23430553
Pubmed	PMID: 3168222
Pubmed	PMID: 19468821
Pubmed	PMID: 31506554
Pubmed	PMID: 2116554
Pubmed	PMID: 19309105
Pubmed	PMID: 25536744
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 8087979
Pubmed	PMID: 4837567
Pubmed	PMID: 2091926
Pubmed	PMID: 17022649
Pubmed	PMID: 32966057
Pubmed	PMID: 15651030
Pubmed	PMID: 24909877
Pubmed	PMID: 6790852
Pubmed	PMID: 4837567
Pubmed	PMID: 15168722
Pubmed	PMID: 7320149
Pubmed	PMID: 25012580
Pubmed	PMID: 25213569
Pubmed	PMID: 466810
Pubmed	PMID: 9686366
Pubmed	PMID: 25754623
Pubmed	PMID: 12101068
Pubmed	PMID: 19217890
Pubmed	PMID: 10102904
Pubmed	PMID: 9732980
Pubmed	PMID: 8178819
Pubmed	PMID: 16789974
Pubmed	PMID: 3873535
Pubmed	PMID: 30830347

)

Disposition

Biological location

Non-excretory biofluid

Blood

Excreta

Feces
Urine

Physical Properties

State

Solid

Experimental Molecular 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)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	131.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002096

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.189	31661259
DarkChem	[M-H]-	127.649	31661259
AllCCS	[M+H]+	132.148	32859911
AllCCS	[M-H]-	128.567	32859911
DeepCCS	[M+H]+	133.146	30932474
DeepCCS	[M-H]-	129.877	30932474
DeepCCS	[M-2H]-	166.935	30932474
DeepCCS	[M+Na]+	142.455	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	127.6	32859911
AllCCS	[M+NH4]+	136.4	32859911
AllCCS	[M+Na]+	137.6	32859911
AllCCS	[M-H]-	128.6	32859911
AllCCS	[M+Na-2H]-	129.8	32859911
AllCCS	[M+HCOO]-	131.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
ortho-Hydroxyphenylacetic acid	OC(=O)CC1=C(O)C=CC=C1	2955.5	Standard polar	33892256
ortho-Hydroxyphenylacetic acid	OC(=O)CC1=C(O)C=CC=C1	1427.8	Standard non polar	33892256
ortho-Hydroxyphenylacetic acid	OC(=O)CC1=C(O)C=CC=C1	1510.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
ortho-Hydroxyphenylacetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1O	1503.4	Semi standard non polar	33892256
ortho-Hydroxyphenylacetic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC=C1CC(=O)O	1554.6	Semi standard non polar	33892256
ortho-Hydroxyphenylacetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1O[Si](C)(C)C	1566.8	Semi standard non polar	33892256
ortho-Hydroxyphenylacetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1O	1740.7	Semi standard non polar	33892256
ortho-Hydroxyphenylacetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1CC(=O)O	1790.5	Semi standard non polar	33892256
ortho-Hydroxyphenylacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1O[Si](C)(C)C(C)(C)C	2044.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0920000000-ca3851c9928227913a97	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (2 TMS)	splash10-0w29-1970000000-de8569a7d279b97680a4	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - ortho-Hydroxyphenylacetic acid EI-B (Non-derivatized)	splash10-0002-0960000000-1018d2254ff44190f41a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-ca3851c9928227913a97	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (Non-derivatized)	splash10-0w29-1970000000-de8569a7d279b97680a4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-0a090cff04cd89d36022	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (2 TMS) - 70eV, Positive	splash10-004i-6930000000-1903392fd44f061e93eb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ortho-Hydroxyphenylacetic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-000i-0900000000-c0378212353f9c247060	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-0a4i-0900000000-2e1d10888e4b882683d4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-0a4i-1900000000-87d962f7cd6aa06c4832	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0a4i-0900000000-e7c99cfd03a6c025cf2c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0900000000-e7c99cfd03a6c025cf2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-69f9fe8670d9a6ce3b78	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Positive-QTOF	splash10-0a4i-0900000000-77bc386fb6ce14ec2dd1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Positive-QTOF	splash10-004i-9000000000-7fb7c81915195d105078	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Positive-QTOF	splash10-0a4i-0900000000-8f1c3458a31199029d71	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Positive-QTOF	splash10-0a4i-5900000000-b7dfc901d3e6c4db398b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Positive-QTOF	splash10-004i-9100000000-e31e91ce81a098f17944	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Positive-QTOF	splash10-0a4i-1900000000-e7bfeba3bf5179c0cbfb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Positive-QTOF	splash10-0a4i-0900000000-0c76ffcb76d341ed2f1d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Positive-QTOF	splash10-0a6r-7900000000-1b46df694de9c5dd84ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 35V, Negative-QTOF	splash10-0a4i-0900000000-81d25cd8f42ea4104dc9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Positive-QTOF	splash10-004i-9000000000-4ad240d4583d43a1ec3e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Negative-QTOF	splash10-0a4i-1900000000-bd8c8286e031da5cb96c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Negative-QTOF	splash10-0udi-8900000000-1c3e198c05d77bf0541f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Negative-QTOF	splash10-0a4i-0900000000-17130a549d9e41fac3f6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Positive-QTOF	splash10-000i-0900000000-6a2b0b911cb357174c27	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Positive-QTOF	splash10-0a4i-1900000000-06436376438e44718bb7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Positive-QTOF	splash10-056r-9300000000-19f4bd2f314d6c0b49bd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 10V, Negative-QTOF	splash10-0zfr-0900000000-c00a2e1956529eb24b43	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 20V, Negative-QTOF	splash10-0pc0-0900000000-a60511b0d00662895871	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ortho-Hydroxyphenylacetic acid 40V, Negative-QTOF	splash10-0a59-4900000000-68a51d2b15b093ce1545	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	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
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21330412	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	26709303	details
Feces	Detected but not Quantified	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	Analysis of 30 no...	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	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	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 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	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	Analysis of 30 no...	details
Urine	Detected and Quantified	0.603 +/- 0.339 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	1.226 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	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
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

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

MarkerDB ID

MDB00000211

Good Scents ID

rw1176931

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

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 ]
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 ]

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)

MOL for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

3D MOL for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

3D SDF for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

3D-SDF for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

PDB for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

3D PDB for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

SMILES for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

INCHI for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

Structure for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

3D Structure for HMDB0000669 (ortho-Hydroxyphenylacetic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions