基本情報
- 標準SMILES
Nc1c(O)cccc1C(=O)O- InChIKey
WJXSWCUQABXPFS-UHFFFAOYSA-N- 分子式
- C7H7NO3
- 平均分子量
- 153.14 g/mol
- 単同位体質量
- 153.04259308
概要
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.
名称と識別子
- 優先名称
- 3-Hydroxyanthranilic Acid
- IUPAC
- 2-amino-3-hydroxybenzoic acid
- 現地名
- 3-ヒドロキシアントラニル酸
- 英語名
- 3-Hydroxyanthranilic acid
- 分子式
- C7H7NO3
- 分子量
- 153.14
名称と別名
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
名称をさらに表示
3-ヒドロキシアントラニル酸2-アミノ-3-ヒドロキシベンゼンカルボン酸3-ヒドロキシ-2-アミノ安息香酸2-アミノ-3-ヒドロキシ安息香酸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
データベース識別子
- CAS
548-93-6- PubChem CID
- 86
- DTXSID
DTXSID40203290- ChEMBL
CHEMBL445304- ChEBI
CHEBI:15793- UNII
- 1UQB1BT4OT
- EC Number
- 208-962-5
- Nikkaji
- J1.608J
物性
構造計算による物性
- XLogP
- 0.9
- 極性表面積
- 83.6 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 4
- 回転可能結合数
- 1
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 160
実験および物理化学的性質
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]+
物理化学的性質
- 融点
- 240 °C · 240 °C (dec.)(lit.)
- 沸点
- 276.03 °C · 276.03°C (rough estimate)
- 比重(密度)
- 1.3585 · 1.3585 (rough estimate)
- 屈折率
- 1.55 · 1.5500 (estimate)
- 貯蔵温度
- Keep in dark place,Sealed in dry,Room Temperature
- 溶解性
- DMSO（微量）、メタノール（微量、加温）
- 外見
- 液体または低融点固体
- 酸解離定数(Pka)
- 1 · pK1: 2.5(+1);pK2: 5.192(0);pK3: 10.118(OH) (25°C)
- 色
- 無色透明～白色～黄色～橙色
- 主な用途
- ペプチド合成
- 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 データベース
- 548 · 548-93-6(CAS DataBase Reference)
安全と法規制
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (97.6%)
毒性情報
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.
安全データ
- wgk
- 3
- rtecs
- DG2625000
- hs_code
- 29225000
- risk_code
- 20/21/22-36/37/38-40
- hazard_code
- Xn
- safety_code
- 22-26-36
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 548-93-6(Hazardous Substances Data)
化学と産業
薬理情報
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
用途と製造
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
応用分野
使用3-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.
調製方法
純化方法The hydrochloride has m 227o (from dilute HCl). [Beilstein 14 H 587, 14 III 1463, 14 IV 2071.] Possible carcinogen.
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補足説明
定義ChEBI: 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.
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