Bovine Metabolome Database: Showing metabocard for 3-Hydroxyanthranilic acid (BMDB0001476)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:46:30 UTC

Update Date

2020-05-21 16:28:50 UTC

BMDB ID

BMDB0001476

Secondary Accession Numbers

BMDB01476

Metabolite Identification

Common Name

3-Hydroxyanthranilic acid

Description

3-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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-3-hydroxy-benzoic acid	ChEBI
2-Amino-3-hydroxybenzoic acid	ChEBI
3-Ohaa	ChEBI
3-Oxyanthranilic acid	ChEBI
2-Amino-3-hydroxy-benzoate	Generator
2-Amino-3-hydroxybenzoate	Generator
3-Oxyanthranilate	Generator
3-Hydroxyanthranilate	Generator
3-Hydroxanthranilate	HMDB
3-Hydroxy-2-aminobenzoate	HMDB
3-Hydroxy-2-aminobenzoic acid	HMDB
3-Hydroxy-anthranilate	HMDB
3-Hydroxy-anthranilic acid	HMDB
3-Hydroxy-anthranilsaeure	HMDB
3-Hydroxyantranilic acid	HMDB
3-OH-Anthranilic acid	HMDB
3 Hydroxyanthranilic acid	HMDB
Acid, 3-hydroxyanthranilic	HMDB

Chemical Formula

C₇H₇NO₃

Average Molecular Weight

153.1354

Monoisotopic Molecular Weight

153.042593095

IUPAC Name

2-amino-3-hydroxybenzoic acid

Traditional Name

3-hydroxyanthranilic acid

CAS Registry Number

548-93-6

SMILES

NC1=C(O)C=CC=C1C(O)=O

InChI Identifier

InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)

InChI Key

WJXSWCUQABXPFS-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:15793 )
aminobenzoic acid (CHEBI:15793 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.81	ALOGPS
logP	1.15	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40 m³·mol⁻¹	ChemAxon
Polarizability	14.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0zfv-0945000000-e3389ab25b7133eb184d	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0zfu-1955000000-fd51cc45bf09750e2b48	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0zfv-0945000000-e3389ab25b7133eb184d	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zfu-1955000000-fd51cc45bf09750e2b48	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0zfv-0934000000-11e2b38a36cb364bcaf3	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0920000000-a57d310e9ca51aefd0c1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zg0-2900000000-f4f0b5c84821e81f2eea	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-6390000000-71ab4928435b01bf5b59	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-2313e347dd8659099393	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9400000000-4e342fdebc8145b606a1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-ee5255b437ae762be1f9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000t-2900000000-a68dc7ca20e1f9595f15	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-0900000000-ced0a738a11057bc94e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0900000000-cded3154e50c6169c670	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0900000000-9c388fc3035f19e3f156	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-1900000000-9dbb06a7728aab173e0f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-0900000000-19cfe2cda31cf7284669	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-02ae2bd70b54df77aca5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-56e21a4ececd5541a7d8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-052r-0900000000-e3015612b3d263fabaa9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a5i-3900000000-670c7d91a38e852d8e4c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-5900000000-36b3a876d06807eb22a3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-052r-0900000000-e3015612b3d263fabaa9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a5i-3900000000-670c7d91a38e852d8e4c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-56e21a4ececd5541a7d8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-02ae2bd70b54df77aca5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-053i-3900000000-a410eeec27727c997dc7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-84ae4ad8e91e8e4b6a6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9i-1900000000-6695f66ad1f45898b8b6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pxr-9300000000-43045627b8c856bf07d2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-0900000000-810a4a12ecb151ecb516	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1900000000-9f194909a88a4ac248b1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8900000000-608d595690e7902b6195	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Bladder
Epidermis
Leukocyte
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tryptophan Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Leukocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001476

DrugBank ID

DB03644

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010582

KNApSAcK ID

C00007568

Chemspider ID

KEGG Compound ID

C00632

BioCyc ID

3-HYDROXY-ANTHRANILATE

BiGG ID

1485273

Wikipedia Link

3-hydroxyanthranilic_acid

METLIN ID

3275

PubChem Compound

PDB ID

Not Available

ChEBI ID

15793

References

Synthesis Reference

Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Catalase

General function:: Inorganic ion transport and metabolism
Specific function:: Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells.
Gene Name:: CAT
Uniprot ID:: P00432
Molecular weight:: 59915.0

Reactions

2 3-Hydroxyanthranilic acid + Oxygen → Cinnavalininate +2 Water	details

Enzyme Details

2. 3-hydroxyanthranilate 3,4-dioxygenase

General function:: Involved in 3-hydroxyanthranilate 3,4-dioxygenase activity
Specific function:: Catalyzes the oxidative ring opening of 3-hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate.
Gene Name:: HAAO
Uniprot ID:: Q0VCA8
Molecular weight:: 32493.0

Reactions

3-Hydroxyanthranilic acid + Oxygen → 2-Amino-3-carboxymuconic acid semialdehyde	details

Enzyme Details

3. Kynureninase

General function:: Not Available
Specific function:: Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:: KYNU
Uniprot ID:: F1MCH2
Molecular weight:: 52186.0

Reactions

L-3-Hydroxykynurenine + Water → 3-Hydroxyanthranilic acid + L-Alanine	details

Showing metabocard for 3-Hydroxyanthranilic acid (BMDB0001476)

Structure for BMDB0001476 (3-Hydroxyanthranilic acid)

Enzymes

Reactions

Reactions

Reactions