(R)-1-tert-Butyl-3-(4-methoxy-benzenesulfonyl)-6-oxo-hexahydro-pyrimidine-4-carboxylic acid hydroxyamide

ID: ALA7108

PubChem CID: 10362663

Max Phase: Preclinical

Molecular Formula: C16H23N3O6S

Molecular Weight: 385.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CN(C(C)(C)C)C(=O)C[C@@H]2C(=O)NO)cc1

Standard InChI:  InChI=1S/C16H23N3O6S/c1-16(2,3)18-10-19(13(9-14(18)20)15(21)17-22)26(23,24)12-7-5-11(25-4)6-8-12/h5-8,13,22H,9-10H2,1-4H3,(H,17,21)/t13-/m1/s1

Standard InChI Key:  VAQNHYAKIUNIKM-CYBMUJFWSA-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
    2.9417   -1.4375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -3.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -3.5042    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
    3.7417   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -3.9167    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
    2.9417   -4.7375    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
    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
    6.1167   -0.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -4.4917    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  1  1  0
  4  5  1  0
  5  1  1  0
  6  4  1  0
  7  3  1  0
  3  8  1  6
  9  2  1  0
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 11  2  2  0
 12  2  2  0
 13  6  2  0
 14  8  2  0
 15  8  1  0
 16  9  2  0
 17  9  1  0
 18 19  1  0
 19 17  2  0
 20 16  1  0
 21 15  1  0
 22 18  1  0
 23 10  1  0
 24 10  1  0
 25 10  1  0
 26 22  1  0
  7  6  1  0
 20 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA7108

   (4R)-1-tert-butyl-N-hydroxy-3-(4-methoxyphenyl)sulfonyl-6-oxo-1,3-diazinane-4-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: 0.55

#Rotatable Bonds: 4

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: 0.10

CX LogD: 0.08

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: -0.93

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]

2. Verma RP, Hansch C..  (2007)  Matrix metalloproteinases (MMPs): chemical-biological functions and (Q)SARs.,  15  (6): [PMID:17275314] [10.1016/j.bmc.2007.01.011]

Source

Source(1):

• Scientific Literature