Biphenyl-2-carboxylic acid {4-[8-(2-pyrrolidin-1-yl-ethyl)-5,6,7,8-tetrahydro-1-thia-4,8-diaza-azulene-4-carbonyl]-phenyl}-amide

ID: ALA176146

PubChem CID: 11272841

Max Phase: Preclinical

Molecular Formula: C33H34N4O2S

Molecular Weight: 550.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(C(=O)N2CCCN(CCN3CCCC3)c3sccc32)cc1)c1ccccc1-c1ccccc1

Standard InChI:  InChI=1S/C33H34N4O2S/c38-31(29-12-5-4-11-28(29)25-9-2-1-3-10-25)34-27-15-13-26(14-16-27)32(39)37-21-8-20-36(33-30(37)17-24-40-33)23-22-35-18-6-7-19-35/h1-5,9-17,24H,6-8,18-23H2,(H,34,38)

Standard InChI Key:  WPUYJTITOZWSHH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
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    2.1917    0.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625    1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792    1.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250    2.3750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -3.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7667    0.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0542    2.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    2.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -5.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792    2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875    3.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -3.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417    4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167    3.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1500   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5 11  1  0
  6  3  1  0
  7  5  1  0
  8  3  1  0
  9  7  2  0
 10  1  1  0
 11 22  1  0
 12 10  2  0
 13  4  1  0
 14 23  1  0
 15  4  2  0
 16  5  2  0
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 19  2  1  0
 20 13  1  0
 21 13  2  0
 22 27  2  0
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 24 19  1  0
 25  6  1  0
 26 20  2  0
 27 21  1  0
 28  7  1  0
 29  9  1  0
 30 14  1  0
 31 14  1  0
 32 18  1  0
 33 18  2  0
 34 35  1  0
 35 28  2  0
 36 31  1  0
 37 30  1  0
 38 33  1  0
 39 32  2  0
 40 38  2  0
  8 12  1  0
 24 25  1  0
 26 22  1  0
 37 36  1  0
 29 34  2  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA176146

   2-phenyl-N-[4-[8-(2-pyrrolidin-1-ylethyl)-6,7-dihydro-5H-thieno[2,3-b][1,4]diazepine-4-carbonyl]phenyl]benzamide

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: 550.73

Molecular Weight (Monoisotopic): 550.2402

AlogP: 6.62

#Rotatable Bonds: 7

Polar Surface Area: 55.89

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 6.04

CX LogD: 4.63

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.28

Np Likeness Score: -1.50

References

1. Cho H, Murakami K, Nakanishi H, Fujisawa A, Isoshima H, Niwa M, Hayakawa K, Hase Y, Uchida I, Watanabe H, Wakitani K, Aisaka K..  (2004)  Synthesis and structure-activity relationships of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine derivatives: novel arginine vasopressin antagonists.,  47  (1): [PMID:14695824] [10.1021/jm030287l]

Source

Source(1):

• Scientific Literature