(R)-5-Hydroxycarbamoyl-4-(4-methoxy-benzenesulfonyl)-[1,4]diazepane-1-carboxylic acid benzyl ester

ID: ALA267939

PubChem CID: 44263913

Max Phase: Preclinical

Molecular Formula: C21H25N3O7S

Molecular Weight: 463.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CCN(C(=O)OCc3ccccc3)CC[C@@H]2C(=O)NO)cc1

Standard InChI:  InChI=1S/C21H25N3O7S/c1-30-17-7-9-18(10-8-17)32(28,29)24-14-13-23(12-11-19(24)20(25)22-27)21(26)31-15-16-5-3-2-4-6-16/h2-10,19,27H,11-15H2,1H3,(H,22,25)/t19-/m1/s1

Standard InChI Key:  XDYZXHJJAIXYOR-LJQANCHMSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
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    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
    3.7167   -4.8125    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
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    3.6792   -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
    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
    2.1417   -1.6500    0.0000 O   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
    3.2542   -5.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4292   -5.4375    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
    1.9667   -6.1167    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
    1.1500   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -6.8542    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
    1.8667   -7.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875   -6.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -7.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  6  1  0
  3  5  1  6
  6 12  1  0
  7  2  1  0
  8  3  1  0
  9  1  1  0
 10  1  2  0
 11  1  2  0
 12  7  1  0
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 15  4  2  0
 16  5  2  0
 17  5  1  0
 18  9  2  0
 19  9  1  0
 20 13  1  0
 21 23  1  0
 22 18  1  0
 23 19  2  0
 24 17  1  0
 25 20  1  0
 26 21  1  0
 27 25  2  0
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 29 26  1  0
 30 28  2  0
 31 27  1  0
 32 30  1  0
 22 21  2  0
  6 14  1  0
 31 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA267939

   (R)-5-Hydroxycarbamoyl-4-(4-methoxy-benzenesulfonyl)-[1,4]diazepane-1-carboxylic acid benzyl ester

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: 463.51

Molecular Weight (Monoisotopic): 463.1413

AlogP: 1.60

#Rotatable Bonds: 6

Polar Surface Area: 125.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 1.23

CX LogD: 1.21

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: -1.31

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