(R)-4-(4-Methoxy-benzenesulfonyl)-1-(1-methyl-1H-imidazole-4-sulfonyl)-[1,4]diazepane-5-carboxylic acid hydroxyamide

ID: ALA268114

PubChem CID: 44263994

Max Phase: Preclinical

Molecular Formula: C17H23N5O7S2

Molecular Weight: 473.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CCN(S(=O)(=O)c3cn(C)cn3)CC[C@@H]2C(=O)NO)cc1

Standard InChI:  InChI=1S/C17H23N5O7S2/c1-20-11-16(18-12-20)31(27,28)21-8-7-15(17(23)19-24)22(10-9-21)30(25,26)14-5-3-13(29-2)4-6-14/h3-6,11-12,15,24H,7-10H2,1-2H3,(H,19,23)/t15-/m1/s1

Standard InChI Key:  CNDCCBOSTVCBMM-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
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    2.9417   -1.4375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1917   -5.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -4.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -4.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8667   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5167   -1.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -2.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -0.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4 10  1  0
  5  3  1  0
  6 13  1  0
  7  1  1  0
  8  3  2  0
  6  9  1  6
 10 15  1  0
 11  5  2  0
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 13 20  1  0
 14  2  1  0
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 24 14  1  0
 25 26  1  0
 26 24  2  0
 27 23  1  0
 28 22  1  0
 29 12  1  0
 30 25  1  0
 31 30  1  0
 11 12  1  0
  4  6  1  0
 27 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA268114

   (5R)-N-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(1-methylimidazol-4-yl)sulfonyl-1,4-diazepane-5-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: 473.53

Molecular Weight (Monoisotopic): 473.1039

AlogP: -0.61

#Rotatable Bonds: 6

Polar Surface Area: 151.14

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.71

CX Basic pKa: 2.53

CX LogP: -0.81

CX LogD: -0.83

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: -1.58

References

1. Pikul S, Dunham KM, Almstead NG, De B, Natchus MG, Taiwo YO, Williams LE, Hynd BA, Hsieh LC, Janusz MJ, Gu F, Mieling GE..  (2001)  Heterocycle-based MMP inhibitors with P2' substituents.,  11  (8): [PMID:11327577] [10.1016/s0960-894x(01)00137-8]

Source

Source(1):

• Scientific Literature