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

ID: ALA3142586

PubChem CID: 71486407

Max Phase: Preclinical

Molecular Formula: C19H26Cl2N4S

Molecular Weight: 340.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1CC(N2CCc3cc(NC(=N)c4cccs4)ccc32)CCN1.Cl.Cl

Standard InChI:  InChI=1S/C19H24N4S.2ClH/c1-13-11-16(6-8-21-13)23-9-7-14-12-15(4-5-17(14)23)22-19(20)18-3-2-10-24-18;;/h2-5,10,12-13,16,21H,6-9,11H2,1H3,(H2,20,22);2*1H

Standard InChI Key:  HACQZEHXKZTINR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.3000  -30.6429    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2567  -28.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2556  -28.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9703  -29.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685  -27.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6839  -28.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6842  -28.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4746  -29.2117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9629  -28.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742  -27.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5421  -27.7156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279  -28.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133  -27.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281  -28.9531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0992  -26.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092  -26.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390  -27.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384  -27.9842    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7297  -29.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1764  -30.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4286  -31.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350  -31.5641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7890  -30.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5365  -30.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5954  -31.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2396  -26.4166    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
 23 25  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: 340.50

Molecular Weight (Monoisotopic): 340.1722

AlogP: 3.69

#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: 10.06

CX LogP: 3.20

CX LogD: 0.50

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: -0.91

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]

3. 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]

4. 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