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Showing Compound 3-Hydroxyanthranilic acid (FDB010582)

Record Information
Version1.0
Creation date2010-04-08 22:09:12 UTC
Update date2024-11-29 22:25:23 UTC
Primary IDFDB010582
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Hydroxyanthranilic acid
Description3-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxyanthranilic acid is a strong basic compound (based on its pKa). 3-Hydroxyanthranilic acid exists in all living species, ranging from bacteria to humans. 3-Hydroxyanthranilic acid has been detected, but not quantified in, brassicas. This could make 3-hydroxyanthranilic acid a potential biomarker for the consumption of these foods.
CAS Number548-93-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Amino-3-hydroxy-benzoic acidChEBI
2-Amino-3-hydroxybenzoic acidChEBI
3-OhaaChEBI
3-Oxyanthranilic acidChEBI
2-Amino-3-hydroxy-benzoateGenerator
2-Amino-3-hydroxybenzoateGenerator
3-OxyanthranilateGenerator
3-HydroxyanthranilateGenerator
3-HydroxanthranilateHMDB
3-Hydroxy-2-aminobenzoateHMDB
3-Hydroxy-2-aminobenzoic acidHMDB
3-Hydroxy-anthranilateHMDB
3-Hydroxy-anthranilic acidHMDB
3-Hydroxy-anthranilsaeureHMDB
3-Hydroxyantranilic acidHMDB
3-OH-Anthranilic acidHMDB
3 Hydroxyanthranilic acidHMDB
Acid, 3-hydroxyanthranilicHMDB
2-amino-3-Hydroxy-benzoateGenerator
2-amino-3-Hydroxy-benzoic acidChEBI
2-amino-3-Hydroxybenzoic acidChEBI
3-Hydroxyanthranilic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP0.81ALOGPS
logP1.15ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H7NO3
IUPAC name2-amino-3-hydroxybenzoic acid
InChI IdentifierInChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
InChI KeyWJXSWCUQABXPFS-UHFFFAOYSA-N
Isomeric SMILESNC1=C(O)C=CC=C1C(O)=O
Average Molecular Weight153.1354
Monoisotopic Molecular Weight153.042593095
Classification
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Benzoic acid
  • O-aminophenol
  • Aminophenol
  • Benzoyl
  • Aniline or substituted anilines
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 54.90%; H 4.61%; N 9.15%; O 31.34%DFC
Melting PointMp 164°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa3 10.12 (20°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3-Hydroxyanthranilic acid, non-derivatized, GC-MS Spectrumsplash10-0zfv-0945000000-e3389ab25b7133eb184dSpectrum
GC-MS3-Hydroxyanthranilic acid, 3 TMS, GC-MS Spectrumsplash10-0zfu-1955000000-fd51cc45bf09750e2b48Spectrum
GC-MS3-Hydroxyanthranilic acid, non-derivatized, GC-MS Spectrumsplash10-0zfv-0945000000-e3389ab25b7133eb184dSpectrum
GC-MS3-Hydroxyanthranilic acid, non-derivatized, GC-MS Spectrumsplash10-0zfu-1955000000-fd51cc45bf09750e2b48Spectrum
GC-MS3-Hydroxyanthranilic acid, non-derivatized, GC-MS Spectrumsplash10-0zfv-0934000000-11e2b38a36cb364bcaf3Spectrum
GC-MS3-Hydroxyanthranilic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0920000000-a57d310e9ca51aefd0c1Spectrum
Predicted GC-MS3-Hydroxyanthranilic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zg0-2900000000-f4f0b5c84821e81f2eeaSpectrum
Predicted GC-MS3-Hydroxyanthranilic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-6390000000-71ab4928435b01bf5b59Spectrum
Predicted GC-MS3-Hydroxyanthranilic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Hydroxyanthranilic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-2313e347dd86590993932012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9400000000-4e342fdebc8145b606a12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-ee5255b437ae762be1f92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000t-2900000000-a68dc7ca20e1f9595f152017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0900000000-ced0a738a11057bc94e42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-cded3154e50c6169c6702017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-9c388fc3035f19e3f1562017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-9dbb06a7728aab173e0f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-19cfe2cda31cf72846692017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-02ae2bd70b54df77aca52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-56e21a4ececd5541a7d82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052r-0900000000-e3015612b3d263fabaa92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a5i-3900000000-670c7d91a38e852d8e4c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-5900000000-36b3a876d06807eb22a32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-052r-0900000000-e3015612b3d263fabaa92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-3900000000-670c7d91a38e852d8e4c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-56e21a4ececd5541a7d82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-02ae2bd70b54df77aca52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-053i-3900000000-a410eeec27727c997dc72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-84ae4ad8e91e8e4b6a6b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-1900000000-6695f66ad1f45898b8b62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-9300000000-43045627b8c856bf07d22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-810a4a12ecb151ecb5162016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-9f194909a88a4ac248b12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-608d595690e7902b61952016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Spectrum
ChemSpider ID84
ChEMBL IDCHEMBL445304
KEGG Compound IDC00632
Pubchem Compound ID86
Pubchem Substance IDNot Available
ChEBI ID15793
Phenol-Explorer IDNot Available
DrugBank IDDB03644
HMDB IDHMDB01476
CRC / DFC (Dictionary of Food Compounds) IDFFC99-D:FFC99-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1485273
KNApSAcK IDC00007568
HET ID3HA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID2-Amino-3-hydroxybenzoic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-hydroxyanthranilate 3,4-dioxygenaseHAAOP46952
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
Metabolism and Physiological Effects of Quinolinic Acid SMP0123249 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference