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

ID: ALA7756

PubChem CID: 44264021

Max Phase: Preclinical

Molecular Formula: C16H23N3O6S

Molecular Weight: 385.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H23N3O6S/c1-11(2)18-8-9-19(14(10-15(18)20)16(21)17-22)26(23,24)13-6-4-12(25-3)5-7-13/h4-7,11,14,22H,8-10H2,1-3H3,(H,17,21)/t14-/m1/s1

Standard InChI Key:  HTNLSTWGHBHDPS-CQSZACIVSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  1  0  0  0  0  0999 V2000
    2.9417   -1.4375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.2625    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
    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
    3.8667   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -1.6500    0.0000 O   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
    2.1792   -4.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    3.7167   -4.8125    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
    4.3167   -1.8000    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
    5.1125   -1.5792    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
    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
    3.2542   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -4.8750    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
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6 10  1  0
  3  7  1  6
  8  2  1  0
  9  1  1  0
 10  8  1  0
 11  1  2  0
 12  1  2  0
 13  5  2  0
 14  7  2  0
 15  7  1  0
 16  6  1  0
 17  9  1  0
 18  9  2  0
 19 20  2  0
 20 18  1  0
 21 17  2  0
 22 15  1  0
 23 19  1  0
 24 16  1  0
 25 16  1  0
 26 23  1  0
 19 21  1  0
  6  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA7756

   (5R)-N-hydroxy-4-(4-methoxyphenyl)sulfonyl-7-oxo-1-propan-2-yl-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: 385.44

Molecular Weight (Monoisotopic): 385.1308

AlogP: 0.20

#Rotatable Bonds: 5

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: -0.29

CX LogD: -0.31

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -1.12

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