(+)-Chloroquine

Details

• Internal ID: 25c2e14e-006b-4ed0-b5b3-c03291d84d17
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Aminoquinolines and derivatives > 4-aminoquinolines
• IUPAC Name: (4S)-4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
• InChI: InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)/t14-/m0/s1
• InChI Key: WHTVZRBIWZFKQO-AWEZNQCLSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆ClN₃
• Molecular Weight: 319.90 g/mol
• Exact Mass: 319.1815255 g/mol
• Topological Polar Surface Area (TPSA): 28.20 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.81
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

• (+)-Chloroquine
• 58175-86-3
• Chloroquine, (S)-
• CHEBI:39254
• 34P96M7C4K
• (S)-N4-(7-chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine
• (+)-N(4)-(7-chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine
• (4S)-N(4)-(7-chloroquinolin-4-yl)-N(1),N(1)-diethylpentane-1,4-diamine
• (4s)-N~4~-(7-Chloroquinolin-4-Yl)-N~1~,N~1~-Diethylpentane-1,4-Diamine
• Chloroquine, D-
• 0TX
• CAS-50-63-5
• Lopac-C-6628
• NCGC00015256-01
• SCHEMBL8934
• BIDD:PXR0167
• UNII-34P96M7C4K
• CHEMBL250447
• (S)-(+)-CHLOROQUINE
• DTXSID401316967
• NCGC00016223-01
• PD070331
• E80613
• Q27119790
• (+)-N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine
• 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, (+)-
• 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, (4S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9839	98.39%
Caco-2	+	0.6682	66.82%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Lysosomes	0.8743	87.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9443	94.43%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8503	85.03%
P-glycoprotein inhibitior	-	0.8404	84.04%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6586	65.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4501	45.01%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9218	92.18%
CYP1A2 inhibition	-	0.8586	85.86%
CYP2C8 inhibition	+	0.6217	62.17%
CYP inhibitory promiscuity	-	0.5496	54.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6847	68.47%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9774	97.74%
Skin irritation	-	0.7352	73.52%
Skin corrosion	-	0.8988	89.88%
Ames mutagenesis	+	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9368	93.68%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.8238	82.38%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8535	85.35%
Acute Oral Toxicity (c)	II	0.7370	73.70%
Estrogen receptor binding	-	0.8693	86.93%
Androgen receptor binding	-	0.5902	59.02%
Thyroid receptor binding	+	0.7649	76.49%
Glucocorticoid receptor binding	-	0.7335	73.35%
Aromatase binding	+	0.6000	60.00%
PPAR gamma	+	0.5590	55.90%
Honey bee toxicity	-	0.9309	93.09%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.8900	89.00%
Fish aquatic toxicity	+	0.9880	98.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4105907	Q5BJF2	Sigma intracellular receptor 2	501.19 nM	Ki	via Super-PRED
CHEMBL287	Q99720	Sigma opioid receptor	79.43 nM	Ki	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	10 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	98.19%	89.76%
CHEMBL3401	O75469	Pregnane X receptor	97.01%	94.73%
CHEMBL2581	P07339	Cathepsin D	96.60%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.63%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.32%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.82%	91.11%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	91.57%	100.00%
CHEMBL2916	O14746	Telomerase reverse transcriptase	90.86%	90.00%
CHEMBL202	P00374	Dihydrofolate reductase	90.57%	89.92%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	90.26%	97.23%
CHEMBL226	P30542	Adenosine A1 receptor	89.85%	95.93%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	89.21%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.99%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	88.27%	90.17%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	87.50%	89.44%
CHEMBL3902	P09211	Glutathione S-transferase Pi	87.35%	93.81%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.17%	96.90%
CHEMBL255	P29275	Adenosine A2b receptor	85.96%	98.59%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	85.95%	92.29%
CHEMBL220	P22303	Acetylcholinesterase	85.87%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.28%	90.71%
CHEMBL3524	P56524	Histone deacetylase 4	85.11%	92.97%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.84%	86.33%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	83.03%	99.00%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	82.29%	92.50%
CHEMBL3232685	O00257	E3 SUMO-protein ligase CBX4	81.10%	93.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.22%	94.00%

Plants that contains it

• Alkanna orientalis

Cross-Links

• PubChem: 639540
• LOTUS: LTS0258327
• wikiData: Q27119790