Dexverapamil

Details

• Internal ID: 9cf6ec27-866a-44db-8023-32323fc34c8a
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylbutylamines
• IUPAC Name: (2R)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
• SMILES (Canonical): CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
• SMILES (Isomeric): CC(C)[C@@](CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC
• InChI: InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3/t27-/m1/s1
• InChI Key: SGTNSNPWRIOYBX-HHHXNRCGSA-N
• Popularity: 37,303 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈N₂O₄
• Molecular Weight: 454.60 g/mol
• Exact Mass: 454.28315770 g/mol
• Topological Polar Surface Area (TPSA): 64.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 5.09
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 13

Synonyms

• 38321-02-7
• Dexverapamilum
• (R)-verapamil
• (+)-verapamil
• Dexverapamilo
• Dexverapamil [INN]
• (+)-(R)-verapamil
• (R)-(+)-verapamil
• d-verapamil
• Verapamil, (r)-
• R(+)-VERAPAMIL
• UNII-QR5PYD126V
• Dexverapamilum [INN-Latin]
• QR5PYD126V
• Dexverapamilo [INN-Spanish]
• CHEBI:77734
• EINECS 253-878-4
• (2R)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
• (+)-3-(3,4-dimethoxyphenyl)-6-[(5,6-dimethoxyphenethyl)methylamino]hexane-3-carbonitrile
• (+)-(R)-5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
• (+)-3-(3,4-Dimethoxyphenyl)-6-((5,6-dimethoxyphenethyl)methylamino)hexane-3-carbonitrile
• (R)-5-((3,4-dimethoxyphenethyl)(methyl)amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile
• Verapramil
• verapamil-r
• C27-H38-N2-O4
• Verapamil (r)-form
• CHEMBL197
• VERAPAMIL, (+)-
• SCHEMBL33297
• DTXSID501009404
• VERAPAMIL (R)-FORM [MI]
• VERAPAMIL, (+)-(R)-
• VERAPAMIL, (R)-(+)-
• 2-(3,4-dimethoxy-phenyl)-5-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-2-isopropyl-pentanenitrile
• Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-, (+)-
• BDBM50338982
• DB14063
• NCI60_010786
• Q27147324
• 4-[3,4-dimethoxyphenethyl(methyl)amino]-1-(3,4-dimethoxyphenyl)-1-isopropylbutyl cyanide
• (+)-(2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
• (+)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
• (.ALPHA.R)-.ALPHA.-(3-((2-(3,4-DIMETHOXYPHENYL)ETHYL)METHYLAMINO)PROPYL)-3,4-DIMETHOXY-.ALPHA.-(1-METHYLETHYL)BENZENEACETONITRILE
• (2R)-(+)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
• (2R)-2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
• (S)-2-(3,4-Dimethoxy-phenyl)-5-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-2-isopropyl-pentanenitrile
• (S)-2-(3,4-Dimethoxy-phenyl)-5-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-2-isopropyl-pentanenitrile; hydrochloride
• (Verapamil) 2-(3,4-Dimethoxy-phenyl)-5-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-2-isopropyl-pentanenitrile
• 5-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-amino}-2-isopropyl-2-(3,4,5-trimethoxy-phenyl)-pentanenitrile
• 5-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-amino}-2-isopropyl-2-(4-methoxy-phenyl)-pentanenitrile
• BENZENEACETONITRILE, .ALPHA.-(3-((2-(3,4-DIMETHOXYPHENYL)ETHYL)METHYLAMINO)PROPYL)-3,4-DIMETHOXY-.ALPHA.-(1-METHYLETHYL)-, (R)-
• I6H
• Verapamil;2-(3,4-Dimethoxy-phenyl)-5-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-2-isopropyl-pentanenitrile

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9735	97.35%
Caco-2	+	0.5463	54.63%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5532	55.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.7532	75.32%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	+	0.9390	93.90%
P-glycoprotein inhibitior	+	0.9674	96.74%
P-glycoprotein substrate	+	0.9291	92.91%
CYP3A4 substrate	+	0.7963	79.63%
CYP2C9 substrate	-	0.5000	50.00%
CYP2D6 substrate	+	0.6427	64.27%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9553	95.53%
CYP2C8 inhibition	+	0.6246	62.46%
CYP inhibitory promiscuity	-	0.9181	91.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7623	76.23%
Carcinogenicity (trinary)	Non-required	0.6565	65.65%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9582	95.82%
Skin irritation	-	0.7995	79.95%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9552	95.52%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	II	0.7343	73.43%
Estrogen receptor binding	+	0.7477	74.77%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.7590	75.90%
Glucocorticoid receptor binding	-	0.8183	81.83%
Aromatase binding	+	0.7197	71.97%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.6206	62.06%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9798	97.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	5100 nM; 6460 nM	Ki; Ki	PMID: 16248836; PMID: 16248836
CHEMBL240	Q12809	HERG	10 nM	IC50	via Super-PRED
CHEMBL5514	P42858	Huntingtin	35481.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM	Potency	via CMAUP
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	35 nM; 113 nM	Kd; Kd	via Super-PRED; via Super-PRED
CHEMBL4302	P08183	P-glycoprotein 1	2370 nM; 2580 nM	IC50; IC50	PMID: 12477351; PMID: 12569305
CHEMBL1293235	P02545	Prelamin-A/C	11220.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.29%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	96.11%	85.31%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.22%	99.17%
CHEMBL2535	P11166	Glucose transporter	93.86%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.29%	86.33%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	88.93%	92.68%
CHEMBL4581	P52732	Kinesin-like protein 1	88.85%	93.18%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	88.80%	87.16%
CHEMBL1255126	O15151	Protein Mdm4	88.79%	90.20%
CHEMBL3837	P07711	Cathepsin L	88.51%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.25%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.20%	95.89%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.07%	93.65%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.76%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	84.79%	93.31%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	83.64%	96.25%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.52%	93.99%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.49%	89.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.34%	90.71%
CHEMBL5747	Q92793	CREB-binding protein	82.63%	95.12%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.42%	100.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	81.03%	96.86%
CHEMBL249	P25103	Neurokinin 1 receptor	80.58%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.49%	91.11%

Plants that contains it

• Piper nigrum

Cross-Links

• PubChem: 65808
• NPASS: NPC167944
• ChEMBL: CHEMBL197