Showing metabocard for Ortho-Hydroxyphenylacetic acid (BMDB0000669)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:34:38 UTC
Update Date2020-04-22 15:04:42 UTC
BMDB IDBMDB0000669
Secondary Accession Numbers
  • BMDB00669
Metabolite Identification
Common NameOrtho-Hydroxyphenylacetic acid
DescriptionOrtho-hydroxyphenylacetic acid, also known as (O-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, 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. Ortho-hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Ortho-hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. Ortho-hydroxyphenylacetic acid has been found to be associated with several diseases known as eosinophilic esophagitis and irritable bowel syndrome; also ortho-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including phenylketonuria.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(O-Hydroxyphenyl)acetic acidChEBI
2'-Hydroxyphenylacetic acidChEBI
2-Hydroxybenzeneacetic acidChEBI
2-Hydroxyphenylacetic acidChEBI
O-Hydroxyphenylacetic acidChEBI
(O-Hydroxyphenyl)acetateGenerator
2'-HydroxyphenylacetateGenerator
2-HydroxybenzeneacetateGenerator
2-HydroxyphenylacetateGenerator
O-HydroxyphenylacetateGenerator
Ortho-hydroxyphenylacetateGenerator
(2-Hydroxyphenyl)acetateHMDB
(2-Hydroxyphenyl)acetic acidHMDB
(O-Hydroxyphenyl)-acetateHMDB
(O-Hydroxyphenyl)-acetic acidHMDB
2-HPAAHMDB
HydroxyphenylacetateHMDB
Hydroxyphenylacetic acidHMDB
O-Hydroxyphenyl acetic acidHMDB
Ortho-hydroxyphenylacetic acidMeSH
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(2-hydroxyphenyl)acetic acid
Traditional Nameo-hydroxyphenylacetic acid
CAS Registry Number614-75-5
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 KeyCCVYRRGZDBSHFU-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acids
Direct Parent2(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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 - 147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility44 mg/mLNot Available
LogP0.85HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP0.99ALOGPS
logP1.31ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0920000000-ca3851c9928227913a97View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0w29-1970000000-de8569a7d279b97680a4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0960000000-1018d2254ff44190f41aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-ca3851c9928227913a97View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0w29-1970000000-de8569a7d279b97680a4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-0a090cff04cd89d36022View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-6930000000-1903392fd44f061e93ebView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-c0378212353f9c247060View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0900000000-2e1d10888e4b882683d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-1900000000-87d962f7cd6aa06c4832View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-e7c99cfd03a6c025cf2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-e7c99cfd03a6c025cf2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-69f9fe8670d9a6ce3b78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-77bc386fb6ce14ec2dd1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-7fb7c81915195d105078View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-8f1c3458a31199029d71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5900000000-b7dfc901d3e6c4db398bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-e31e91ce81a098f17944View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-e7bfeba3bf5179c0cbfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-0c76ffcb76d341ed2f1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-7900000000-1b46df694de9c5dd84caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-81d25cd8f42ea4104dc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-4ad240d4583d43a1ec3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-bd8c8286e031da5cb96cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-8900000000-1c3e198c05d77bf0541fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-17130a549d9e41fac3f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-6a2b0b911cb357174c27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-06436376438e44718bb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9300000000-19f4bd2f314d6c0b49bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-c00a2e1956529eb24b43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-0900000000-a60511b0d00662895871View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-4900000000-68a51d2b15b093ce1545View in MoNA
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000669
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012331
KNApSAcK IDNot Available
Chemspider ID11476
KEGG Compound IDC05852
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5639
PubChem Compound11970
PDB IDNot Available
ChEBI ID28478
References
Synthesis ReferenceLevine, 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
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]