기본 정보
- CAS
4450-98-0- 표준 SMILES
CCOC(=O)C1=C(O)C(=O)N(Cc2ccccc2)C1- InChIKey
IGYRPDIWSYGHMY-UHFFFAOYSA-N- 분자식
- C14H15NO4
- 평균 분자량
- 261.27 g/mol
- 단동위원소 질량
- 261.10010796
개요
Ethyl 1-benzyl-3-hydroxy- 2-oxo[5H]pyrrole-4-carboxylate is a pyrroline and a carboxylic acid.
이름 및 식별자
- 우선 이름
- Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate
- IUPAC
- ethyl 1-benzyl-4-hydroxy-5-oxo-2H-pyrrole-3-carboxylate
- 영어명
- ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate
- 분자식
- C14H15NO4
- 분자량
- 261.27
이름 및 동의어
4450-98-0Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate1-EbpcMW8LQ9P85CDTXSID50196205NSC-2295301H-Pyrrole-3-carboxylic acid, 2,5-dihydro-4-hydroxy-5-oxo-1-(phenylmethyl)-, ethyl esterRefChem:138475DTXCID20118696EBPC1-Benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl esterMFCD00179167
이름 더 보기
CP-10668Nsc 229530EBPC, 10 mM in DMSOEBPC, Aldose reductase inhibitorAldose Reductase,inhibit,EBPC,Inhibitor1-Benzyl-4-bydroxy-5-oxo-3-pyrroline-3-carboxylic Acid Ethyl Ester2,5-Dihydro-4-hydroxy-5-oxo-1-(phenylMethyl)-1H-pyrrole-3-carboxylic Acid Ethyl Ester
ethyl 1-benzyl-4-hydroxy-5-oxo-2H-pyrrole-3-carboxylateethyl 1-benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylateNSC229530ETHYL 1-BENZYL-3-HYDROXY- 2-OXO[5H]PYRROLE-4-CARBOXYLATENSC 229530;NSC-229530;NSC229530SMR000567214Spectrum_001772SpecPlus_000694
데이터베이스 식별자
- CAS
4450-98-0- PubChem CID
- 54677973
- DTXSID
DTXSID50196205- ChEMBL
CHEMBL269550- ChEBI
CHEBI:190040- UNII
- MW8LQ9P85C
- EC Number
- 662-651-2
- Nikkaji
- J380.653G
물성
구조 계산 물성
- XLogP
- 1.7
- 극성 표면적
- 66.8 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 19
- 형식 전하
- 0
- 복잡도
- 396
실험 및 물리화학적 성질
Solubility>39.2 [ug/mL] (The mean of the results at pH 7.4)
물리화학적 성질
- 녹는점
- 135 · 135-136 °C
- 끓는 점
- 479.8 · 479.8±45.0 °C(Predicted)
- 밀도
- 1.34 · 1.340±0.06 g/cm3(Predicted)
- 저장 조건
- room temp
- 용해도
- 10 mg/mL · DMSO: ≥10mg/mL
- 물리적 상태
- 백색분말
- 산도 계수 (pKa)
- 4.5 · 4.50±1.00(Predicted)
- 색상
- white
- InChI
- 1S/C14H15NO4/c1-2-19-14(18)11-9-15(13(17)12(11)16)8-10-6-4-3-5-7-10/h3-7,16H,2,8-9H2,1H3
- InChIKey
- IGYRPDIWSYGHMY-UHFFFAOYSA-N
- SMILES
- CCOC(=O)C1=C(O)C(=O)N(Cc2ccccc2)C1
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
안전 데이터
- wgk
- 3
- risk_code
- 22-41
- hazard_code
- Xn
- safety_code
- 26
- 위험 등급
- IRRITANT
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
응용 분야
개요The human aldose reductase AKR1B1 is considered the rate limiting enzyme of the polyol pathway responsible for the conversion of glucose into sorbitol. It also acts as a highly efficient PGF2α synthase in response to interleukin-1β. Increased aldose reductase expression has been associated with complications of diabetes and may contribute to reduced efficacy of certain chemotherapeutic drugs. EBPC is a potent, selective inhibitor of aldose reductase with an IC50 value of 47 nM in vitro. Through its regulation of glucose metabolism, EBPC has been used to improve the cytotoxic effects of the anticancer agents doxorubicin and cisplatin in HeLa cervical carcinoma cells. EBPC also inhibits prostaglandin F2α (PGF2α) and PGE2 production in human endometrial cells with an EC50 value of 10 μM.
용도A highly specific aldose reductase inhibitor that has been shown to enhance HeLa cell sensitivity to chemotherapeutic drugs.
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