Cinchonidine

Details

• Internal ID: 0a7b4d20-5e9d-48ab-a12e-3e4fd6fb2483
• Taxonomy: Alkaloids and derivatives > Cinchona alkaloids
• IUPAC Name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• SMILES (Canonical): C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
• SMILES (Isomeric): C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=CC=NC4=CC=CC=C34)O
• InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1
• InChI Key: KMPWYEUPVWOPIM-KODHJQJWSA-N
• Popularity: 222 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.173213330 g/mol
• Topological Polar Surface Area (TPSA): 36.40 Ų
• XlogP: 2.70

Synonyms

• 485-71-2
• (-)-Cinchonidine
• (8S,9R)-Cinchonidine
• Cinchovatine
• alpha-Quinidine
• L-Cinchonidine
• Cinchovatine-
• MFCD00006783
• a-quinidine
• Cinchonan-9-ol, (8a,9R)-
• TCMDC-123934
• cinchonine
• UNII-1U622LRA8Z
• (8S,9R)-cinchonan-9-ol
• (8alpha,9R)-Cinchonan-9-ol
• 1U622LRA8Z
• CHEBI:3703
• 485-71-2 (free base)
• (R)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol
• .alpha.-Quinidine
• NSC-5364
• (8-alpha,9R)-Cinchonan-9-ol
• Cinchonan-9-ol, (8.alpha.,9R)-
• (8alpha,9R)Cinchonan-9-ol
• (R)-4-quinolyl-[(2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol
• NSC 5364
• 2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-
• EINECS 207-622-3
• (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
• (R)-[(4S,5S,7S)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-quinolin-4-ylmethanol
• AI3-15317
• SR-05000001575
• Cinchonan-9-ol, (8alpha,9R)-
• Cinchonan-9-ol, (8-alpha,9R)-
• -Quinidine
• Cinchonan-9-ol, (8a alpha,9R)-
• (-)cinchonidine
• (-) cinchonidine
• Cinchonidine,(S)
• Prestwick_66
• Cinchonidine, 96%
• Spectrum_001165
• Prestwick3_000606
• Spectrum2_000719
• Spectrum3_001745
• Spectrum4_001173
• Spectrum5_002073
• CINCHONIDINE [MI]
• BSPBio_000512
• BSPBio_003450
• KBioGR_001805
• KBioSS_001645
• MLS002153905
• CINCHONIDINE [WHO-DD]
• CINCHONIDINE [WHO-IP]
• DivK1c_000501
• SCHEMBL159532
• SPECTRUM1500839
• SPBio_000937
• BPBio1_000564
• CHEMBL533841
• HMS501J03
• KBio1_000501
• KBio2_001645
• KBio2_004213
• KBio2_006781
• KBio3_002670
• DTXSID60883396
• KMPWYEUPVWOPIM-KODHJQJWSA-N
• NINDS_000501
• HMS1921K14
• HMS2092M14
• HMS2096J14
• HMS2235F22
• Pharmakon1600-01500839
• 118-10-5
• HY-N0173
• STR04708
• CCG-36455
• CCG-37735
• NSC757800
• (-)-Cinchonidine, analytical standard
• AKOS016008633
• NSC-757800
• SDCCGMLS-0066969.P001
• (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• IDI1_000501
• NCGC00178057-01
• NCGC00178057-02
• NCGC00262526-04
• SMR001233254
• SBI-0051617.P002
• QUININE SULFATE IMPURITY B [WHO-IP]
• CS-0007887
• QUININE BISULFATE IMPURITY B [WHO-IP]
• EN300-708682
• F15420
• AB00052182_03
• QUININE SULFATE IMPURITY B [EP IMPURITY]
• Q412713
• SR-05000001575-1
• SR-05000001575-6
• SR-05000001575-7
• SR-05000001575-8
• BRD-K17661460-001-03-2
• BRD-K17661460-001-04-0
• BRD-K39079086-001-05-0
• BRD-K39079086-001-07-6
• Cinchonidine, purum, >=98.0% (dried material, NT)
• QUININE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
• Z1954806302
• QUININE BISULFATE HEPTAHYDRATE IMPURITY B [WHO-IP]
• (-)-Cinchonidine, 99% (total base), may cont. up to 5% quinine
• (1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol
• (R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol
• (2S,4S,8R,alphaR)-alpha-(4-Quinolyl)-8-vinyl-1-azabicyclo[2.2.2]octane-2-methanol
• (S)-[(2R,4R,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• (R)-((2S,4S,5R)-5-ETHENYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(QUINOLIN-4-YL)METHANOL [WHO-IP]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	96.43%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.07%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.31%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.66%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.31%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.94%	95.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	87.88%	98.33%
CHEMBL4302	P08183	P-glycoprotein 1	87.72%	92.98%
CHEMBL3902	P09211	Glutathione S-transferase Pi	87.58%	93.81%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.22%	95.83%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	86.08%	91.43%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.94%	94.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.17%	94.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.70%	95.89%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	84.48%	96.47%
CHEMBL1951	P21397	Monoamine oxidase A	83.67%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.27%	99.23%
CHEMBL2581	P07339	Cathepsin D	81.86%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.64%	89.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.08%	100.00%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	80.72%	88.42%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.45%	94.62%

Plants that contains it

• Cinchona calisaya
• Cinchona pubescens
• Dendrosenecio kilimanjari subsp. kilimanjari

Cross-Links

• PubChem: 101744
• NPASS: NPC203754
• ChEMBL: CHEMBL533841
• LOTUS: LTS0145071
• wikiData: Q412713