Onalespib

HCID 11955716

기본 정보

CAS: 912999-49-6
표준 SMILES: CC(C)c1cc(C(=O)N2Cc3ccc(CN4CCN(C)CC4)cc3C2)c(O)cc1O
InChIKey: IFRGXKKQHBVPCQ-UHFFFAOYSA-N
분자식: C24H31N3O3
평균 분자량: 409.5 g/mol
단동위원소 질량: 409.23654185

개요

Onalespib is a member of the class of isoindoles that is isoindole in which the amino group has been acylated by a 2,4-dihydroxy-5-isopropylbenzoyl group and in which position 5 of the isoidole moiety has been substituted by a (4-methylpiperazin-1-yl)methyl group. A second-generation Hsp90 inhibitor. It has a role as an antineoplastic agent and a Hsp90 inhibitor. It is a tertiary carboxamide, a member of benzamides, a member of isoindoles, a member of resorcinols and a N-alkylpiperazine.

이름 및 식별자

우선 이름: Onalespib
IUPAC: (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone
영어명: Onalespib
분자식: C24H31N3O3
분자량: 409.52

이름 및 동의어

Onalespib912999-49-6AT13387AT-13387AT 13387onalespibumQ7Y33N57ZZATI13387XATI-13387X(2,4-Dihydroxy-5-isopropylphenyl)-(5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl)methanoneCHEBI:140592DTXSID80238485

이름 더 보기

CS-1866ATI-13387AT13387, >=98%Onalespib LactateAT13387(Onalespib)ATI-13387

Methanone, (1,3-dihydro-5-((4-methyl-1-piperazinyl)methyl)-2H-isoindol-2-yl)(2,4-dihydroxy-5-(1-methylethyl)phenyl)-4-{5-[(4-methylpiperazin-1-yl)methyl]-2,3-dihydro-1H-isoindole-2-carbonyl}-6-(propan-2-yl)benzene-1,3-diol4-(5-((4-methylpiperazin-1-yl)methyl)-2,3-dihydro-1H-isoindole-2-carbonyl)-6-(propan-2-yl)benzene-1,3-diolRefChem:856776DTXCID00160976Onalespib (AT13387)(2,4-Dihydroxy-5-isopropylphenyl)(5-((4-methylpiperazin-1-yl)methyl)isoindolin-2-yl)methanone912999-49-6 (free base)

데이터베이스 식별자

CAS: 912999-49-6
PubChem CID: 11955716
DTXSID: DTXSID80238485
ChEMBL: CHEMBL1214827
ChEBI: CHEBI:140592
UNII: Q7Y33N57ZZ
Nikkaji: J3.146.978C

물성

구조 계산 물성

XLogP: 3.1
극성 표면적: 67.3 Å²
수소 결합 공여자 수: 2
수소 결합 수용자 수: 5
회전 가능 결합 수: 4
무거운 원자 수: 30
형식 전하: 0
복잡도: 592

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

LogP2.87

물리화학적 성질

끓는 점: 605.7 · 605.7±55.0 °C(Predicted)
밀도: 1.237 · 1.237
저장 조건: -20 °C · Store at -20°C
용해도: 2 O; · insoluble in H2O; ≥13.25 mg/mL in DMSO; ≥47.7 mg/mL in EtOH with ultrasonic
물리적 상태: 고체
산도 계수 (pKa): 8.5 · 8.50±0.48(Predicted)
색상: White to off-white
InChI: InChI=1S/C24H31N3O3/c1-16(2)20-11-21(23(29)12-22(20)28)24(30)27-14-18-5-4-17(10-19(18)15-27)13-26-8-6-25(3)7-9-26/h4-5,10-12,16,28-29H,6-9,13-15H2,1-3H3
InChIKey: IFRGXKKQHBVPCQ-UHFFFAOYSA-N
SMILES: C(N1CC2=C(C1)C=CC(CN1CCN(C)CC1)=C2)(C1=CC(C(C)C)=C(O)C=C1O)=O

안전 및 규제

안전 데이터

신호 어: Warning
유해·위험 문구: 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302

화학 및 산업

응용 분야 · 1건

개요Onalespib, also known as AT13387, is a selective inhibitor of Hsp90 (IC50 = 18 nM). It induces the degradation of specific Hsp90 client proteins, including mutant EGFR, for up to seven days in tumor cell lines in vitro and up to three days in vivo. Onalespib is retained in tumor xenografts and is efficacious in a range of xenograft models. It differs from other HSP90 inhibitors in its longer duration of target inhibition and its favorable toxicity profile in phase I studies in patients with refractory solid tumors.