6-benzyl-2-(5-nitrothiophene-2-carboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

ID: ALA3752173

PubChem CID: 5096507

Max Phase: Preclinical

Molecular Formula: C20H18N4O4S2

Molecular Weight: 442.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(NC(=O)c2ccc([N+](=O)[O-])s2)sc2c1CCN(Cc1ccccc1)C2

Standard InChI:  InChI=1S/C20H18N4O4S2/c21-18(25)17-13-8-9-23(10-12-4-2-1-3-5-12)11-15(13)30-20(17)22-19(26)14-6-7-16(29-14)24(27)28/h1-7H,8-11H2,(H2,21,25)(H,22,26)

Standard InChI Key:  WUCTZQDTJCQEQP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -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 N   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 S   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
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808    3.5211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    2.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187   -1.4919    0.0000 C   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
   -4.9282   -3.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9331   -5.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6365   -5.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350   -5.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301   -3.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3513   -1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2606   -2.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2249   -2.4499    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6461   -1.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6290   -0.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1973   -0.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8699   -2.8344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9599   -2.3324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7602   -4.0294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  0
 10 12  2  0
  9 10  1  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 22  2  0
 28 29  2  0
 28 30  1  0
 25 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3752173

   6-benzyl-2-[(5-nitrothiophene-2-carbonyl)amino]-5,7-dihydro-4H-thieno[2,3-c]pyridine-3-carboxamide

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: 442.52

Molecular Weight (Monoisotopic): 442.0769

AlogP: 3.63

#Rotatable Bonds: 6

Polar Surface Area: 118.57

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.17

CX Basic pKa: 6.63

CX LogP: 4.37

CX LogD: 4.30

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: -2.23

References

1. Malothu N, Bhandaru JS, Kulandaivelu U, Jojula M, Adidala RR, K R U, A V N D, Kaki VR, Akkinepally RR..  (2016)  Synthesis, in vitro antimycobacterial evaluation and docking studies of some new 5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one schiff bases.,  26  (3): [PMID:26755393] [10.1016/j.bmcl.2015.12.083]

Source

Source(1):

• Scientific Literature