Identification
Name3-Hydroxyanthranilic Acid
Accession NumberDB03644  (EXPT00171)
TypeSmall Molecule
GroupsExperimental
Description

An oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen. [PubChem]

Structure
Thumb
Synonyms
2-Amino-3-hydroxy-benzoic acid
2-Amino-3-Hydroxybenzoic Acid
3-HYDROXY-ANTHRANILATE
3-Hydroxy-anthranilsaeure
3-hydroxyanthranilate
3-Oxyanthranilic acid
External IDs NSC-522891
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII1UQB1BT4OT
CAS number548-93-6
WeightAverage: 153.1354
Monoisotopic: 153.042593095
Chemical FormulaC7H7NO3
InChI KeyWJXSWCUQABXPFS-UHFFFAOYSA-N
InChI
InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
IUPAC Name
2-amino-3-hydroxybenzoic acid
SMILES
NC1=C(O)C=CC=C1C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Trans-2,3-dihydro-3-hydroxyanthranilate isomeraseProteinunknownNot AvailablePseudomonas fluorescensQ51792 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Tryptophan MetabolismMetabolicSMP00063
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (58.9 KB)
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)240 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.5 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m3·mol-1ChemAxon
Polarizability14.18 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8669
Blood Brain Barrier-0.9444
Caco-2 permeable-0.7319
P-glycoprotein substrateNon-substrate0.7997
P-glycoprotein inhibitor INon-inhibitor0.9834
P-glycoprotein inhibitor IINon-inhibitor0.9926
Renal organic cation transporterNon-inhibitor0.9565
CYP450 2C9 substrateNon-substrate0.7909
CYP450 2D6 substrateNon-substrate0.8414
CYP450 3A4 substrateNon-substrate0.7764
CYP450 1A2 substrateNon-inhibitor0.7645
CYP450 2C9 inhibitorNon-inhibitor0.8114
CYP450 2D6 inhibitorNon-inhibitor0.9735
CYP450 2C19 inhibitorNon-inhibitor0.6213
CYP450 3A4 inhibitorNon-inhibitor0.845
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9262
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8719
BiodegradationReady biodegradable0.6606
Rat acute toxicity1.5446 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.964
hERG inhibition (predictor II)Non-inhibitor0.9446
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Download (8.79 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0zfv-0945000000-e3389ab25b7133eb184dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfu-1955000000-fd51cc45bf09750e2b48View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0zfv-0934000000-11e2b38a36cb364bcaf3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-2313e347dd8659099393View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9400000000-4e342fdebc8145b606a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-ee5255b437ae762be1f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0900000000-ced0a738a11057bc94e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-cded3154e50c6169c670View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-9c388fc3035f19e3f156View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-9dbb06a7728aab173e0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0900000000-19cfe2cda31cf7284669View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-02ae2bd70b54df77aca5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-56e21a4ececd5541a7d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-052r-0900000000-e3015612b3d263fabaa9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a5i-3900000000-670c7d91a38e852d8e4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-5900000000-36b3a876d06807eb22a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative ParentsAminobenzoic acids / Benzoic acids / o-Aminophenols / Benzoyl derivatives / Aniline and substituted anilines / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Primary aromatic amines / Vinylogous amides / Amino acids
SubstituentsAminobenzoic 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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsmonohydroxybenzoic acid, aminobenzoic acid (CHEBI:15793 )

Targets

Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
unknown
General Function:
Isomerase activity
Specific Function:
Isomerase that catalyzes the condensation of two molecules of trans-2,3-dihydro-3-hydroxyanthranilic acid (DHHA) into the phenazine ring system. The final product is not yet known.
Gene Name:
phzF
Uniprot ID:
Q51792
Molecular Weight:
30052.965 Da
References
  1. Blankenfeldt W, Kuzin AP, Skarina T, Korniyenko Y, Tong L, Bayer P, Janning P, Thomashow LS, Mavrodi DV: Structure and function of the phenazine biosynthetic protein PhzF from Pseudomonas fluorescens. Proc Natl Acad Sci U S A. 2004 Nov 23;101(47):16431-6. Epub 2004 Nov 15. [PubMed:15545603 ]
Drug created on June 13, 2005 07:24 / Updated on June 24, 2017 13:21