Basic information
- Standard SMILES
Nc1c(O)cccc1C(=O)O- InChIKey
WJXSWCUQABXPFS-UHFFFAOYSA-N- Molecular formula
- C7H7NO3
- Average molar mass
- 153.14 g/mol
- Monoisotopic mass
- 153.04259308
Overview
3-hydroxyanthranilic acid is an aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan. It has a role as a mouse metabolite and a human metabolite. It is an aminobenzoic acid and a monohydroxybenzoic acid. It is functionally related to an anthranilic acid. It is a conjugate acid of a 3-hydroxyanthranilate. It is a tautomer of a 2,3-dihydro-3-oxoanthranilic acid.
Names & identifiers
- Preferred name
- 3-Hydroxyanthranilic Acid
- IUPAC
- 2-amino-3-hydroxybenzoic acid
- English name
- 3-Hydroxyanthranilic acid
- Molecular formula
- C7H7NO3
- Molecular weight
- 153.14
Names & synonyms
2-Amino-3-hydroxybenzoic acid3-Hydroxyanthranilic acid548-93-63-Ohaa3-hydroxyanthranilate2-AMINO-3-HYDROXY-BENZOIC ACIDAnthranilic acid, 3-hydroxy-Benzoic acid, 2-amino-3-hydroxy-1UQB1BT4OTDTXSID40203290NSC-522891CHEBI:15793
Show more names
3-HYDROXY-ANTHRANILATE3-HYDROXYANTHRANILLIC ACIDNSC 522891JACS-548-93-63-oxyanthranilicacid3-Oxyanthranilic acidMesalazine Impurity 413-Hydroxy-anthranilsaeure
CHEBI:365593 Hydroxyanthranilic AcidAcid, 3-HydroxyanthranilicRefChem:94252DTXCID40125781208-962-52-amino-3-hydroxybenzoate3-Hydroxy anthranilic acid
Database identifiers
- CAS
548-93-6- PubChem CID
- 86
- DTXSID
DTXSID40203290- ChEMBL
CHEMBL445304- ChEBI
CHEBI:15793- UNII
- 1UQB1BT4OT
- EC Number
- 208-962-5
- Nikkaji
- J1.608J
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 83.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 160
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Color/FormLEAFLETS IN WATER
SolubilitySLIGHTLY SOL IN WATER, SOL IN HOT WATER, ALCOHOL, ETHER; SOL IN CHLOROFORM
Melting Point164 °C
Physical DescriptionSolid
Collision Cross Section
131.2 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
131.3 Ų [M+H]+
Physicochemical properties
- Melting point
- 240 °C · 240 °C (dec.)(lit.)
- Boiling point
- 276.03 °C · 276.03°C (rough estimate)
- Density
- 1.3585 · 1.3585 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Liquid or Low Melting Solid
- pka
- 1 · pK1: 2.5(+1);pK2: 5.192(0);pK3: 10.118(OH) (25°C)
- color
- Clear colorless to white to yellow to orange
- Major Application
- peptide synthesis
- InChI
- InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
- InChIKey
- WJXSWCUQABXPFS-UHFFFAOYSA-N
- SMILES
- C(O)(=O)C1=CC=CC(O)=C1N
- CAS DataBase Reference
- 548 · 548-93-6(CAS DataBase Reference)
- FDA UNII
- 1 UQB1BT4OT · 1UQB1BT4OT
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332-H315-H319-H335-H351
- Precautionary statements
- 280 · P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22-36/37/38-40
- Safety Statements
- 22 · 22-26-36
- WGK Germany
- 3 · 3
- RTECS
- 2625000 · DG2625000
- HS Code
- 29225000 · 29225000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 548 · 548-93-6(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.6%)
Toxicology
Interactions
TRYPTOPHAN ADMIN RAISED OUTPUT OF FREE FORM /OF 3-HYDROXYANTHRANILIC ACID/ PRINCIPALLY IN HUMAN URINE...
EFFECT OF CIGARETTE SMOKING ON (CARCINOGEN) 3-HYDROXY ANTHRANILIC ACID EXCRETION WAS STUDIED ON 20 NORMAL INDIVIDUALS IN FASTING STATE. SMOKING INCR EXCRETION OF THIS METABOLITE IN URINE SIGNIFICANTLY.
Human Toxicity Excerpts
SINCE FREE FORM WITH CARCINOGENIC POTENTIAL WAS EXCRETED...& INCR ONLY IN SUBJECTS TREATED WITH TRYPTOPHAN, RELATIONSHIP /WITH/...CARCINOGENESIS... RELEVANT TO MAN. ... INTAKE OF TRYPTOPHAN &/OR RATE OF TRYPTOPHAN METAB... IMPORTANT, SINCE RATES OF HYDROLYSIS OF 3-HYDROXYANTHRANILIC ACID CONJUGATES ARE TOO SLOW...
PATTERNS OF URINARY EXCRETION OF FREE & CONJUGATED FORMS OF 3-HYDROXYANTHRANILIC ACID CHANGE STRIKINGLY IN DIFFERENT SPECIES OF MAMMALS, & THIS MAY BE IMPORTANT SINCE 3-HYDROXYANTHRANILIC ACID, A TRYPTOPHAN METABOLITE, IS SUSPECTED OF CAUSING BLADDER CANCER.
THE POSSIBLE ROLE OF ENDOGENOUS TRYPTOPHAN METABOLITES & OF 1 TYROSINE METABOLITE IN INDUCING BLADDER CANCER IN HUMANS IS DISCUSSED.
Non-Human Toxicity Excerpts
...REPORTED TO INDUCE CHROMATID BREAKS IN CULTURED HUMAN EMBRYO CELLS @ CONCN OF 30 MG/L. ONE CHROMOSOME TRANSLOCATION WAS OBSERVED IN 338 METAPHASE CELLS EXAMINED; NONE WERE SEEN IN 300 CONTROL METAPHASE CELLS.
CARCINOGENIC EFFECT WAS SHOWN BY 3-HYDROXYANTHRANILIC ACID IMPLANTED INTO THE BLADDER WALL IN MICE.
RESULTS DID NOT SUPPORT HYPOTHESIS THAT TRYPTOPHAN METABOLITES PRODUCED BY INTESTINAL MICROFLORA ARE MAJOR ETIOLOGIC FACTORS IN CANCER OF COLON, THEY WERE NEG IN AMES TEST.
3-HYDROXYANTHRANILIC ACID ADMIN SC TO MICE @ 2.5 MG TWICE WEEKLY FOR 10 WK INDUCED TUMORS IN THE URINARY BLADDER.
PRESENCE OF 20% 3-HYDROXYANTHRANILIC ACID IN THE PELLETS MADE NO CHANGE IN THE INCIDENCE OF TUMORS.
Probable Routes of Human ExposureHYDROXYANTHRANILIC ACID WAS FOUND IN BOTH SERUM & BLOOD CLOTS OF WORKERS CONTACTING ANILINE DYES.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- DG2625000
- hs_code
- 29225000
- risk_code
- 20/21/22-36/37/38-40
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 22-26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302+H312+H332-H315-H319-H335-H351
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313
- Hazardous Substances Data
- 548-93-6(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
YIELDS 2-AMINO-3-CARBOXYPHENYL SULFATE IN GUINEA PIGS, MICE & RATS; WATANABE M & MINEGISHI K, BIOCHEM PHARMAC, 21, 1347 (1972). YIELDS CINNABARINIC ACID IN RATS; SUBBA RAO PV & VAIDYANATHAN CS, BIOCHEM J, 99, 317 (1966). IN MICE, MORGAN LR, SINGH R, SYLVES T V & WEIMORTS D, CANCER RES, 27, 2395 (1967). /FROM TABLE/
YIELDS ALPHA-AMINO-BETA-CARBOXYMUCONIC SEMIALDEHYDE IN PIG. WISS O & BETTENDORF G, HOPPE-SEYLER'S Z PHYSIOL CHEM, 306, 10 (1957). YIELDS 2-AMINO-3-CARBOXYPHENYL-BETA-D-GLUCURONIDE IN GUINEA PIGS, MICE, RATS; WATANABE M, CHKUBO K & TAMURA Z, BIOCHEM PHARMAC, 21, 1337 (1972). /FROM TABLE/
INCUBATION OF 3-HYDROXYANTHRANILIC ACID WITH 100,000 G SUPERNATANT OF MALE RAT LIVER, PRODUCED TRACES OF 3-METHOXYANTHRANILIC ACID.
NO SIGNIFICANT DIFFERENCES IN LEVEL OF ACTIVITY WERE FOUND AMONG STRAINS FOR HYDROXYANTHRANILATE OXYGENASE.
MeSH Pharmacological ClassificationSubstances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY.
Absorption, Distribution and Excretion
SIGNIFICANT PERCENTAGE OF PT WITH NON-OCCUPATIONAL 'SPONTANEOUS' BLADDER CANCER EXCRETE HIGHER AMT OF...3-HYDROXYANTHRANILIC ACID THAN NORMAL CONTROL INDIVIDUALS...
...EXCRETED MAINLY IN FREE FORM IN HUMAN SUBJECTS, AS SULFATE ESTERS IN RATS, & AS GLUCURONIDES IN GUINEA-PIGS.
FOLLOWING IP INJECTION OF 0.2 MUMOLE (14)C-3-HYDROXYANTHRANILIC ACID TO MICE, 54 & 64% OF (14)C RECOVERED WAS FOUND IN CO2, AFTER 1 & 24 HR, RESPECTIVELY. AT 24 HR CARCASS & FECES CONTAINED 19% OF (14)C, & ONLY 17% WAS FOUND IN URINE.
AFTER SC INJECTION OF (3)H-LABELED 3-HYDROXYANTHRANILIC ACID INTO MICE, (3)H WAS DISTRIBUTED MAINLY IN LIVER & KIDNEYS, & AFTER 6 HR, (3)H REMAINED IN LYMPHOID ORGANS.
For more Absorption, Distribution and Excretion (Complete) data for 2-AMINO-3-HYDROXY-BENZOIC ACID (6 total), please visit the HSDB record page.
Tissue LocationsBladder
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism
Uses & manufacturing
Uses
NONE
BIOLOGICAL INTERMEDIATE IN THE CONVERSION OF TRYPTOPHAN TO ACETYL-COENZYME A; BIOLOGICAL INTERMEDIATE IN THE BIOSYNTHESIS OF NIACIN FROM TRYPTOPHAN IN NIACIN-DEFICIENT ANIMALS
U.S. Exports
(1975) No Data
(1977) No Data
U.S. Imports
(1975) No Data
(1977) No Data
U.S. Production
(1975) NOT PRODUCED COMMERCIALLY IN US
(1977) NOT PRODUCED COMMERCIALLY IN US
Applications
Uses3-Hydroxyanthranilic Acid is one of the tryptophan’s metabolites along the kynurenine pathway. 3-Hydroxyanthranilic Acid has been shown to induce apoptosis in T cells.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: An aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan.
Related reactions
39 records
Linked notes
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