Dequalinium

Details

• Internal ID: 67a5fa58-cf79-4cb5-bfed-a6554b5c958b
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Aminoquinolines and derivatives > 4-aminoquinolines
• IUPAC Name: 1-[10-(4-amino-2-methylquinolin-1-ium-1-yl)decyl]-2-methylquinolin-1-ium-4-amine
• InChI: InChI=1S/C30H38N4/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3/p+2
• InChI Key: PCSWXVJAIHCTMO-UHFFFAOYSA-P
• Popularity: 327 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀N₄+₂
• Molecular Weight: 456.70 g/mol
• Exact Mass: 456.32529729 g/mol
• Topological Polar Surface Area (TPSA): 59.80 Ų
• XlogP: 7.30
• Atomic LogP (AlogP): 6.17
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 11

Synonyms

• 6707-58-0
• Dequalinium cation
• E7QC7V26B8
• CHEBI:41872
• 1-[10-(4-amino-2-methylquinolin-1-ium-1-yl)decyl]-2-methylquinolin-1-ium-4-amine
• DTXSID4046941
• 1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM)
• Dynexan MHP
• 1-(10-(4-amino-2-methylquinolin-1-ium-1-yl)decyl)-2-methylquinolin-1-ium-4-amine
• Diiodide, Dequalinium
• Dibromide, Dequalinium
• RefChem:132044
• Diundecenoate, Dequalinium
• Di-10-undecenoate, Dequalinium
• DTXCID2026941
• 1,1'-(1,10-Decanediyl)bis(4-amino-2-methylquinolinium)
• Dequadin
• dequaliniumchloride
• Dequavagyn
• Dekadin
• Dequavet
• Labosept
• Oralgol
• Rumilet
• Sanoral
• Sentril
• Ivazil
• Sorot
• Dequadin chloride
• Dequalin chloride
• 1,1'-(Decane-1,10-diyl)bis(4-amino-2-methylquinolin-1-ium)
• DEQ
• 1,1'-decane-1,10-diylbis(4-amino-2-methylquinolinium)
• 1-[10-(4-amino-2-methylquinolyl)decyl]-2-methyl-4-quinolylamine
• CHEMBL121663
• 1-[10-(4-Amino-2-methyl-quinolin-1-yl)decyl]-2-methyl-quinolin-4-amine dichloride
• CHEMBL1256847
• NCGC00015339-02
• CAS-522-51-0
• Decamethylenebis(4-aminoquinaldinium chloride)
• UNII-E7QC7V26B8
• Dequqlinium
• Spectrum_000151
• Tocris-0674
• starbld0000847
• Prestwick0_000388
• Prestwick1_000388
• Prestwick2_000388
• Prestwick3_000388
• Spectrum2_000650
• Spectrum4_000757
• Spectrum5_001086
• Lopac-D-3768
• NCIMech_000681
• Efisol (*dichloride salt*)
• Evazol (*dichloride salt*)
• Lopac0_000338
• BSPBio_000575
• DEQUALINIUM [WHO-DD]
• Erosept (*dichloride salt*)
• KBioGR_001114
• KBioSS_000631
• Decamine (*dichloride salt*)
• Dequadin (*dichloride salt*)
• DivK1c_000752
• Grocreme (*dichloride salt*)
• SCHEMBL149457
• SPBio_000659
• SPBio_002496
• BPBio1_000633
• CHEMBL333826
• GTPL2313
• orb1740582
• SCHEMBL29557297
• SCHEMBL29577841
• KBio1_000752
• KBio2_000631
• KBio2_003199
• KBio2_005767
• NINDS_000752
• PCSWXVJAIHCTMO-UHFFFAOYSA-P
• Quinolinium, 1,1'-(1,10-decanediyl)bis(4-amino-2-methyl-
• BDBM50048403
• BDBM50473222
• CCG-35859
• STL483403
• STL483697
• AKOS024284388
• DB04209
• 1-[10-(4-amino-2-methyl-quinolin-1-ium-1-yl)decyl]-2-methyl-quinolin-1-ium-4-amine
• IDI1_000752
• QTL1_000029
• NCGC00015339-01
• NCGC00015339-03
• NCGC00015339-04
• NCGC00015339-05
• NCGC00015339-07
• NCGC00015339-08
• NCGC00015339-12
• NCGC00024723-01
• NCGC00024723-02
• NCI60_001298
• ST075548
• SBI-0050326.P003
• NS00008690
• BRD-K77685957-300-01-8
• BRD-K77685957-300-08-3
• BRD-K77685957-300-09-1
• 1, {10-Decamethylenebis[4-aminoquinaldinium} chloride]
• Quinaldinium, 1,1'-decamethylenebis[4-amino]- dichloride
• 1,1'-decane-1,10-diylbis(2-methylquinolin-4(1H)-iminium)
• Quinolinium, 1,1'-(1, {10-decanediyl)bis[4-amino-2-methyl-,} dichloride
• 1,1''-(Deca-4,6-diyne-1,10-diyl)bis(4-amino-2-methylquinolinium) Diiodide Hydrate
• 1-[10-(4-amino-2-methyl-1-quinoliniumyl)decyl]-2-methyl-4-quinoliniumamine
• 1-[10-(4-amino-2-methyl-1-quinoliniumyl)decyl]-2-methyl-4-quinoliniumamine dichloride
• 1-[10-(4-amino-2-methyl-1-quinoliniumyl)decyl]-2-methyl-4-quinoliniumamine(Deq)
• 1-[10-(4-amino-2-methyl-1-quinoliniumyl)decyl]-2-methyl-4-quinoliniumamine(dequalinium)
• 1-(10-(4-Amino-2-methyl-1lambda~5~-quinolin-1-yl)decyl)-2-methyl-1lambda~5~-quinolin-4-ylamine dichloride
• 1-[10-(4-amino-2-methyl-1-quinoliniumyl)decyl]-2-methyl-4-quinoliniumamine dichloride ; Dequalinium
• DQ+

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7952	79.52%
Caco-2	-	0.7405	74.05%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Nucleus	0.6736	67.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9375	93.75%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.8750	87.50%
BSEP inhibitior	+	0.9097	90.97%
P-glycoprotein inhibitior	+	0.8365	83.65%
P-glycoprotein substrate	-	0.6420	64.20%
CYP3A4 substrate	-	0.5386	53.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7273	72.73%
CYP3A4 inhibition	+	0.6677	66.77%
CYP2C9 inhibition	-	0.9119	91.19%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	-	0.6703	67.03%
CYP2C8 inhibition	+	0.4567	45.67%
CYP inhibitory promiscuity	+	0.5512	55.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6176	61.76%
Eye corrosion	-	0.9809	98.09%
Eye irritation	-	0.9354	93.54%
Skin irritation	-	0.6785	67.85%
Skin corrosion	-	0.9160	91.60%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8528	85.28%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.5557	55.57%
skin sensitisation	-	0.8710	87.10%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7824	78.24%
Acute Oral Toxicity (c)	III	0.5940	59.40%
Estrogen receptor binding	+	0.8318	83.18%
Androgen receptor binding	+	0.7676	76.76%
Thyroid receptor binding	+	0.7252	72.52%
Glucocorticoid receptor binding	+	0.6686	66.86%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.7117	71.17%
Honey bee toxicity	-	0.9491	94.91%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.8100	81.00%
Fish aquatic toxicity	+	0.9314	93.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	19952.6 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	39810.7 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM	Potency	via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	10000 nM; 15848.93 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	15848.9 nM; 31622.8 nM; 10000 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	1584.9 nM; 3162.3 nM; 6309.6 nM; 3162.3 nM; 6309.6 nM; 1584.9 nM	Potency; Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	19952.6 nM; 31622.8 nM; 15848.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL5514	P42858	Huntingtin	7943.3 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	1995.3 nM; 10000 nM; 10000 nM; 1995.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	3162.3 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	794.3 nM; 794.3 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	18492.7 nM; 7362.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	12589.3 nM	Potency	via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31.6 nM; 7943.3 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	22387.2 nM; 44668.4 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.10%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.47%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	92.26%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.45%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.67%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.53%	86.33%
CHEMBL3902	P09211	Glutathione S-transferase Pi	83.03%	93.81%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.01%	93.65%

Plants that contains it

• Lagerstroemia indica

Cross-Links

• PubChem: 2993
• NPASS: NPC313449
• ChEMBL: CHEMBL333826