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

ID: ALA3216566

PubChem CID: 71486403

Max Phase: Preclinical

Molecular Formula: C17H22Cl2N4S

Molecular Weight: 312.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(Nc1ccc2c(c1)CCN2C1CCNC1)c1cccs1

Standard InChI:  InChI=1S/C17H20N4S.2ClH/c18-17(16-2-1-9-22-16)20-13-3-4-15-12(10-13)6-8-21(15)14-5-7-19-11-14;;/h1-4,9-10,14,19H,5-8,11H2,(H2,18,20);2*1H

Standard InChI Key:  FPNOONBJFCTROW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    6.0643    0.2469    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
    3.5643   -3.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -4.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -5.0249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -3.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5643    0.2469    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
 22 23  1  0
 23 19  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: 312.44

Molecular Weight (Monoisotopic): 312.1409

AlogP: 2.91

#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: 10.50

CX LogP: 2.72

CX LogD: -0.28

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.60

Np Likeness Score: -1.32

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