N-(2-hydroxyethyl)-4'-((4-oxo-4,5,6,7-tetrahydro-3H-cyclopenta[d]pyrimidin-2-ylthio)methyl)biphenyl-4-sulfonamide

ID: ALA4100008

PubChem CID: 137660260

Max Phase: Preclinical

Molecular Formula: C22H23N3O4S2

Molecular Weight: 457.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(SCc2ccc(-c3ccc(S(=O)(=O)NCCO)cc3)cc2)nc2c1CCC2

Standard InChI:  InChI=1S/C22H23N3O4S2/c26-13-12-23-31(28,29)18-10-8-17(9-11-18)16-6-4-15(5-7-16)14-30-22-24-20-3-1-2-19(20)21(27)25-22/h4-11,23,26H,1-3,12-14H2,(H,24,25,27)

Standard InChI Key:  JRZSRMXZQHPNOV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.5688  -16.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602  -15.8362    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7513  -16.5393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5533  -12.1299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5533  -12.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2627  -13.3557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2627  -11.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9721  -12.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9766  -12.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7559  -13.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2348  -12.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7487  -11.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1338  -12.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4225  -13.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2627  -10.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127  -12.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0019  -13.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0026  -14.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7201  -14.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4279  -14.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2961  -14.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5828  -14.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726  -14.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8745  -15.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5924  -15.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2997  -15.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549  -15.4287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7448  -15.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313  -15.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211  -15.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  7  1  0
  5  6  2  0
  6  9  1  0
  8  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
  7 16  2  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 15  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 19 22  1  0
 25  2  1  0
  2 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100008

   ---

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: 457.58

Molecular Weight (Monoisotopic): 457.1130

AlogP: 2.49

#Rotatable Bonds: 8

Polar Surface Area: 112.15

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.65

CX Basic pKa: 0.55

CX LogP: 2.93

CX LogD: 2.76

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -1.54

References

1. Choi JY, Fuerst R, Knapinska AM, Taylor AB, Smith L, Cao X, Hart PJ, Fields GB, Roush WR..  (2017)  Structure-Based Design and Synthesis of Potent and Selective Matrix Metalloproteinase 13 Inhibitors.,  60  (13): [PMID:28653849] [10.1021/acs.jmedchem.7b00514]

2. Fuerst R, Choi JY, Knapinska AM, Cameron MD, Ruiz C, Delmas A, Sundrud MS, Fields GB, Roush WR..  (2022)  Development of a putative Zn²⁺-chelating but highly selective MMP-13 inhibitor.,  76  [PMID:36202189] [10.1016/j.bmcl.2022.129014]

Source

Source(1):

• Scientific Literature