Cinchonine

HCID 90454CAS 118-10-5

基本情報

標準SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccccc12
InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N
分子式: C19H22N2O
平均分子量: 294.4 g/mol
単同位体質量: 294.17321332

概要

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.

名称と識別子

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

名称と別名

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

名称をさらに表示

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

データベース識別子

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

物性

構造計算による物性

XLogP: 2.7
極性表面積: 36.4 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 3
重原子数: 22
形式電荷: 0
複雑度: 412

実験および物理化学的性質

SpringerMaterials PropertiesCrystal structure

LogP2.68

Collision Cross Section · 2 件

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]

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 3 件

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%)

化学と産業

薬理情報

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)