4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-hydroxymethyl]quinolin-6-ol

Details

• Internal ID: a393468d-a039-4898-bf67-bdc51d6674fd
• Taxonomy: Alkaloids and derivatives > Cinchona alkaloids
• IUPAC Name: 4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-hydroxymethyl]quinolin-6-ol
• SMILES (Canonical): C=CC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)O)O
• SMILES (Isomeric): C=C[C@H]1CN2CCC1C[C@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)O)O
• InChI: InChI=1S/C19H22N2O2/c1-2-12-11-21-8-6-13(12)9-18(21)19(23)15-5-7-20-17-4-3-14(22)10-16(15)17/h2-5,7,10,12-13,18-19,22-23H,1,6,8-9,11H2/t12-,13?,18-,19+/m0/s1
• InChI Key: VJFMSYZSFUWQPZ-BPBOJLQBSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂N₂O₂
• Molecular Weight: 310.40 g/mol
• Exact Mass: 310.168127949 g/mol
• Topological Polar Surface Area (TPSA): 56.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• O-Desmethyl Quinine
• 524-63-0
• 4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-hydroxymethyl]quinolin-6-ol
• hydroxycinchonidine
• 4-[(S)-[(2R,4R,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-hydroxymethyl]quinolin-6-ol
• 6'-Hydroxycinchonidine
• (8-alpha,9R)-Cinchonan-6',9-diol
• VJFMSYZSFUWQPZ-BPBOJLQBSA-N
• AKOS030242372
• C06530
• 4-[(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-hydroxymethyl]quinolin-6-ol
• 4-[(R)-[(2S,5R)-5-Vinyl-1-azabicyclo[2.2.2]octane-2-yl](hydroxy)methyl]-6-hydroxyquinoline

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9720	97.20%
Caco-2	+	0.8284	82.84%
Blood Brain Barrier	+	0.7108	71.08%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7172	71.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9378	93.78%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	0.8005	80.05%
OCT2 inhibitior	+	0.8000	80.00%
BSEP inhibitior	-	0.6609	66.09%
P-glycoprotein inhibitior	+	0.6233	62.33%
P-glycoprotein substrate	+	0.8831	88.31%
CYP3A4 substrate	+	0.6445	64.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4668	46.68%
CYP3A4 inhibition	-	0.8436	84.36%
CYP2C9 inhibition	-	0.9045	90.45%
CYP2C19 inhibition	-	0.9137	91.37%
CYP2D6 inhibition	+	0.6160	61.60%
CYP1A2 inhibition	-	0.7014	70.14%
CYP2C8 inhibition	-	0.9107	91.07%
CYP inhibitory promiscuity	-	0.7509	75.09%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6556	65.56%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9456	94.56%
Skin irritation	+	0.5244	52.44%
Skin corrosion	-	0.9036	90.36%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8518	85.18%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	-	0.8524	85.24%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7984	79.84%
Acute Oral Toxicity (c)	II	0.5478	54.78%
Estrogen receptor binding	-	0.5315	53.15%
Androgen receptor binding	+	0.7654	76.54%
Thyroid receptor binding	-	0.5640	56.40%
Glucocorticoid receptor binding	+	0.5373	53.73%
Aromatase binding	-	0.4927	49.27%
PPAR gamma	-	0.6096	60.96%
Honey bee toxicity	-	0.7036	70.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	-	0.4170	41.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.61%	94.45%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	94.24%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.57%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.88%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.61%	89.62%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	91.35%	96.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.29%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	90.48%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.47%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.30%	95.89%
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	86.12%	97.98%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.50%	92.94%
CHEMBL2581	P07339	Cathepsin D	85.34%	98.95%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	83.81%	91.65%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.10%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.52%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.75%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.33%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.97%	93.40%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.82%	90.24%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	80.69%	98.33%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.53%	91.43%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.39%	99.18%

Plants that contains it

• Cinchona calisaya
• Platycladus orientalis
• Tinadendron noumeanum

Cross-Links

• PubChem: 441075
• NPASS: NPC242808
• LOTUS: LTS0105129
• wikiData: Q105287214