4-butyl-N-(3-((1-methyl-1H-imidazol-5-yl)methyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)benzenesulfonamide

ID: ALA1079868

PubChem CID: 46882457

Max Phase: Preclinical

Molecular Formula: C25H32N4O2S

Molecular Weight: 452.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1ccc(S(=O)(=O)Nc2ccc3c(c2)CCN(Cc2cncn2C)CC3)cc1

Standard InChI:  InChI=1S/C25H32N4O2S/c1-3-4-5-20-6-10-25(11-7-20)32(30,31)27-23-9-8-21-12-14-29(15-13-22(21)16-23)18-24-17-26-19-28(24)2/h6-11,16-17,19,27H,3-5,12-15,18H2,1-2H3

Standard InChI Key:  NEHBJWYHHPCAAH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.1730    1.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8847    1.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828    3.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213    2.4356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1601    1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6052    1.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997    2.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4592    1.5861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8290    0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5446    0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2554    0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4176    2.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8916    1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3821    0.3397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0926    0.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7916    1.7317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2971    2.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
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  6  7  1  0
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  5  8  1  0
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  8  9  1  0
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  5 26  1  0
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  1  2  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1079868

   4-butyl-N-[3-[(3-methylimidazol-4-yl)methyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]benzenesulfonamide

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: 452.62

Molecular Weight (Monoisotopic): 452.2246

AlogP: 4.16

#Rotatable Bonds: 8

Polar Surface Area: 67.23

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 7.74

CX LogP: 3.81

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.56

Np Likeness Score: -1.24

References

1. Bailey JM, Scott JS, Basilla JB, Bolton VJ, Boyfield I, Evans DG, Fleury E, Heightman TD, Jarvie EM, Lawless K, Matthews KL, McKay F, Mok H, Muir A, Orlek BS, Sanger GJ, Stemp G, Stevens AJ, Thompson M, Ward J, Vaidya K, Westaway SM..  (2009)  The discovery and optimisation of benzazepine sulfonamide and sulfones as potent agonists of the motilin receptor.,  19  (22): [PMID:19804969] [10.1016/j.bmcl.2009.09.027]

Source

Source(1):

• Scientific Literature