(R)-3-(4-Methoxy-benzenesulfonyl)-1-(2-methoxy-ethyl)-6-oxo-hexahydro-pyrimidine-4-carboxylic acid hydroxyamide

ID: ALA266292

PubChem CID: 44264020

Max Phase: Preclinical

Molecular Formula: C15H21N3O7S

Molecular Weight: 387.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCN1CN(S(=O)(=O)c2ccc(OC)cc2)[C@@H](C(=O)NO)CC1=O

Standard InChI:  InChI=1S/C15H21N3O7S/c1-24-8-7-17-10-18(13(9-14(17)19)15(20)16-21)26(22,23)12-5-3-11(25-2)4-6-12/h3-6,13,21H,7-10H2,1-2H3,(H,16,20)/t13-/m1/s1

Standard InChI Key:  SUFSQYXUPYDFHG-CYBMUJFWSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  1  0  0  0  0  0999 V2000
    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   -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
    2.2375   -3.5042    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
    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
    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
    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
    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
    4.3750   -3.9167    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
    5.0792   -5.1542    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
    6.7042   -1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  4  1  0
  6  3  1  0
  7  5  1  0
  3  8  1  6
  9  2  1  0
 10  2  2  0
 11  2  2  0
 12  7  2  0
 13  8  2  0
 14  8  1  0
 15  9  1  0
 16  9  2  0
 17  5  1  0
 18 20  2  0
 19 15  2  0
 20 16  1  0
 21 14  1  0
 22 18  1  0
 23 24  1  0
 24 17  1  0
 25 22  1  0
 26 23  1  0
  6  7  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA266292

   (4R)-N-hydroxy-1-(2-methoxyethyl)-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: 387.41

Molecular Weight (Monoisotopic): 387.1100

AlogP: -0.60

#Rotatable Bonds: 7

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: -1.00

CX LogD: -1.03

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -1.15

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