N-(1-(2-(dimethylamino)ethyl)indolin-5-yl)thiophene-2-carboximidamide dihydrochloride

ID: ALA3216124

PubChem CID: 71486265

Max Phase: Preclinical

Molecular Formula: C17H24Cl2N4S

Molecular Weight: 314.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCN1CCc2cc(NC(=N)c3cccs3)ccc21.Cl.Cl

Standard InChI:  InChI=1S/C17H22N4S.2ClH/c1-20(2)9-10-21-8-7-13-12-14(5-6-15(13)21)19-17(18)16-4-3-11-22-16;;/h3-6,11-12H,7-10H2,1-2H3,(H2,18,19);2*1H

Standard InChI Key:  FDFZHBOJCKJPBI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    8.0974    0.0219    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267    2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300    3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905    3.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0779    5.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5472    5.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2884    4.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2772    3.1068    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -4.3539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028   -4.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3299   -5.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5974    0.0219    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
 20 21  1  0
 21 22  1  0
 21 23  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: 314.46

Molecular Weight (Monoisotopic): 314.1565

AlogP: 3.11

#Rotatable Bonds: 5

Polar Surface Area: 42.36

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.96

CX LogP: 3.16

CX LogD: 1.45

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.66

Np Likeness Score: -2.00

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]

Source

Source(1):

• Scientific Literature