(+/-)-N-(1-(Piperidin-3-yl)indolin-5-yl)thiophene-2-carboximidamide dihydrochloride

ID: ALA3217218

PubChem CID: 71486408

Max Phase: Preclinical

Molecular Formula: C18H24Cl2N4S

Molecular Weight: 326.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(Nc1ccc2c(c1)CCN2C1CCCNC1)c1cccs1

Standard InChI:  InChI=1S/C18H22N4S.2ClH/c19-18(17-4-2-10-23-17)21-14-5-6-16-13(11-14)7-9-22(16)15-3-1-8-20-12-15;;/h2,4-6,10-11,15,20H,1,3,7-9,12H2,(H2,19,21);2*1H

Standard InChI Key:  WAIKTIFJOLZDCZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    6.4838   -0.0093    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
    2.1852   -2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6221   -3.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838   -4.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -5.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -5.1227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007   -3.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9838   -0.0093    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
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: 326.47

Molecular Weight (Monoisotopic): 326.1565

AlogP: 3.30

#Rotatable Bonds: 3

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: 9.62

CX LogP: 3.24

CX LogD: 0.92

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -1.27

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