Cinchonine

HCID 90454CAS 118-10-5

기본 정보

표준 SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccccc12
InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N
분자식: C19H22N2O
평균 분자량: 294.4 g/mol
단동위원소 질량: 294.17321332

개요

Cinchonine is cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). It occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis. It has a role as a metabolite. It is an (8xi)-cinchonan-9-ol and a cinchona alkaloid. It derives from a hydride of a cinchonan.

이름 및 식별자

우선 이름: Cinchonine
IUPAC: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol

이름 및 동의어

cinchonine118-10-5D-Cinchonine(9S)-Cinchonan-9-olCinchonan-9-ol, (9S)-(8R,9S)-Cinchonine(+)-CinconineDTXSID6045082NSC-6176V43X79NZCDCHEBI:27509DTXCID801474963

이름 더 보기

2-Quinuclidinemethanol, alpha-(5-vinyl-2-quinolyl)-alpha-(5-Vinyl-2-quinuclidinyl)-4-quinolinemethanol(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol(S)-((2R,4S,5R)-5-ethenyl-1-azabicyclo(2.2.2)octan-2-yl)-quinolin-4-ylmethanolLA-40221RefChem:126196204-234-6(+)-Cinchonine

데이터베이스 식별자

CAS: 118-10-5
PubChem CID: 90454
DTXSID: DTXSID6045082
ChEMBL: CHEMBL588619
ChEBI: CHEBI:27509
UNII: V43X79NZCD
EC Number: 204-234-6
Nikkaji: J2.475I

물성

구조 계산 물성

XLogP: 2.7
극성 표면적: 36.4 Å²
수소 결합 공여자 수: 1
수소 결합 수용자 수: 3
회전 가능 결합 수: 3
무거운 원자 수: 22
형식 전하: 0
복잡도: 412

실험 및 물리화학적 성질

SpringerMaterials PropertiesCrystal structure

LogP2.68

Collision Cross Section · 2건

165.21 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

166.3 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

안전 및 규제

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 65 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 3건

Chemical: Cinchonan-9-ol, (9S)-

Status: Active Update: 13-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/16829

Cinchonan-9-ol, (9S)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (100%)

화학 및 산업

약리 정보

MeSH Pharmacological ClassificationAgents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)