(R)-1-Benzyl-4-(4-methoxy-benzenesulfonyl)-7-oxo-[1,4]diazepane-5-carboxylic acid hydroxyamide

ID: ALA415482

PubChem CID: 44263926

Max Phase: Preclinical

Molecular Formula: C20H23N3O6S

Molecular Weight: 433.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CCN(Cc3ccccc3)C(=O)C[C@@H]2C(=O)NO)cc1

Standard InChI:  InChI=1S/C20H23N3O6S/c1-29-16-7-9-17(10-8-16)30(27,28)23-12-11-22(14-15-5-3-2-4-6-15)19(24)13-18(23)20(25)21-26/h2-10,18,26H,11-14H2,1H3,(H,21,25)/t18-/m1/s1

Standard InChI Key:  GETQXLAMYOMSJS-GOSISDBHSA-N

Molfile:  

     RDKit          2D

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    2.9417   -2.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0167   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -4.0667    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
    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
    3.7417   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -0.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1792   -4.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8042   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5417   -4.8750    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
    6.1167   -0.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -4.1917    0.0000 C   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
    5.8250   -4.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
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  6 12  1  0
  3  7  1  6
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 19 22  2  0
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 24 19  1  0
 25 20  2  0
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 19 21  1  0
  6  5  1  0
 29 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA415482

   (5R)-1-benzyl-N-hydroxy-4-(4-methoxyphenyl)sulfonyl-7-oxo-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: 433.49

Molecular Weight (Monoisotopic): 433.1308

AlogP: 0.99

#Rotatable Bonds: 6

Polar Surface Area: 116.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 0.66

CX LogD: 0.64

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -1.22

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