cis-N-(1-(4-(Methylamino)cyclohexyl)indolin-5-yl)thiophene-2-carboximidamide dihydrochloride

ID: ALA3142587

PubChem CID: 71484435

Max Phase: Preclinical

Molecular Formula: C20H28Cl2N4S

Molecular Weight: 354.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC1CCC(N2CCc3cc(NC(=N)c4cccs4)ccc32)CC1.Cl.Cl

Standard InChI:  InChI=1S/C20H26N4S.2ClH/c1-22-15-4-7-17(8-5-15)24-11-10-14-13-16(6-9-18(14)24)23-20(21)19-3-2-12-25-19;;/h2-3,6,9,12-13,15,17,22H,4-5,7-8,10-11H2,1H3,(H2,21,23);2*1H

Standard InChI Key:  NAUGLCGXQTUMNB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   25.9875  -29.1696    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.7876  -28.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7864  -29.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5011  -29.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4993  -27.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2146  -28.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2148  -29.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0052  -29.2718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4934  -28.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0048  -27.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0730  -27.7757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3587  -28.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6443  -27.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3589  -29.0132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6302  -26.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8404  -26.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3701  -27.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8695  -28.0443    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.2603  -30.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7071  -30.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9593  -31.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7656  -31.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3195  -31.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0670  -30.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0177  -32.4093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4636  -33.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2703  -26.9924    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 13  1  0
  8 19  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 354.52

Molecular Weight (Monoisotopic): 354.1878

AlogP: 4.08

#Rotatable Bonds: 4

Polar Surface Area: 51.15

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.70

CX LogP: 3.88

CX LogD: 0.76

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: -1.25

References

1. Annedi SC, Maddaford SP, Ramnauth J, Renton P, Rybak T, Silverman S, Rakhit S, Mladenova G, Dove P, Andrews JS, Zhang D, Porreca F..  (2012)  Discovery of a potent, orally bioavailable and highly selective human neuronal nitric oxide synthase (nNOS) inhibitor, N-(1-(piperidin-4-yl)indolin-5-yl)thiophene-2-carboximidamide as a pre-clinical development candidate for the treatment of migraine.,  55  [PMID:22840695] [10.1016/j.ejmech.2012.07.006]

2. Annedi SC, Maddaford SP, Ramnauth J, Renton P, Rybak T, Silverman S, Rakhit S, Mladenova G, Dove P, Andrews JS, Zhang D, Porreca F..  (2012)  Discovery of a potent, orally bioavailable and highly selective human neuronal nitric oxide synthase (nNOS) inhibitor, N-(1-(piperidin-4-yl)indolin-5-yl)thiophene-2-carboximidamide as a pre-clinical development candidate for the treatment of migraine.,  55  [PMID:22840695] [10.1016/j.ejmech.2012.07.006]

Source

Source(1):

• Scientific Literature