3-히드록시안트라닐산

3-Hydroxyanthranilic Acid

HCID 86CAS 548-93-6
부분 구조 검색유사 구조 찾기

기본 정보

표준 SMILES
Nc1c(O)cccc1C(=O)O
InChIKey
WJXSWCUQABXPFS-UHFFFAOYSA-N
분자식
C7H7NO3
평균 분자량
153.14 g/mol
단동위원소 질량
153.04259308

개요

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.

이름 및 식별자

우선 이름
3-Hydroxyanthranilic Acid
IUPAC
2-amino-3-hydroxybenzoic acid
현지명
3-히드록시안트라닐산
영어명
3-Hydroxyanthranilic acid
분자식
C7H7NO3
분자량
153.14

이름 및 동의어

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
이름 더 보기
2-아미노-3-하이드록시-벤조산3-히드록시안트라닐산3-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

데이터베이스 식별자

CAS
548-93-6
PubChem CID
86
DTXSID
DTXSID40203290
ChEMBL
CHEMBL445304
ChEBI
CHEBI:15793
UNII
1UQB1BT4OT
EC Number
208-962-5
Nikkaji
J1.608J

물성

구조 계산 물성

XLogP
0.9
극성 표면적
83.6 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
4
회전 가능 결합 수
1
무거운 원자 수
11

실험 및 물리화학적 성질

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 · 2건

131.2 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

131.3 Ų [M+H]+

물리화학적 성질

녹는점
240 °C · 240 °C (dec.)(lit.)
끓는 점
276.03 °C · 276.03°C (rough estimate)
밀도
1.3585 · 1.3585 (rough estimate)
굴절률
1.55 · 1.5500 (estimate)
저장 조건
Keep in dark place,Sealed in dry,Room Temperature
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨, 가열)

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (97.6%)

독성 정보

Interactions · 2건

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 · 3건

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 · 5건

...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.

안전 데이터

wgk
3
rtecs
DG2625000
HS 번호
29225000
risk_code
20/21/22-36/37/38-40
hazard_code
Xn
safety_code
22-26-36

화학 및 산업

약리 정보

Metabolism/Metabolites · 4건

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 · 5건

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

용도 및 제조

Uses · 2건

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 · 2건

(1975) No Data

(1977) No Data

U.S. Imports · 2건

(1975) No Data

(1977) No Data

U.S. Production · 2건

(1975) NOT PRODUCED COMMERCIALLY IN US

(1977) NOT PRODUCED COMMERCIALLY IN US

응용 분야

용도3-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.

상·하류 제품 정보

공급사50 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]

추가 설명

정의ChEBI: 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.

관련 반응

39건
반응 기록 만들기

연결된 노트

불러오는 중…