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

ID: ALA4081997

PubChem CID: 135567320

Max Phase: Preclinical

Molecular Formula: C22H24N4O3S2

Molecular Weight: 456.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCNS(=O)(=O)c1ccc(-c2ccc(CSc3nc4c(c(=O)[nH]3)CCC4)cc2)cc1

Standard InChI:  InChI=1S/C22H24N4O3S2/c23-12-13-24-31(28,29)18-10-8-17(9-11-18)16-6-4-15(5-7-16)14-30-22-25-20-3-1-2-19(20)21(27)26-22/h4-11,24H,1-3,12-14,23H2,(H,25,26,27)

Standard InChI Key:  YDCCHZDGDMSTQT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   15.8238  -16.7235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4193  -16.0178    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0062  -16.7209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8083  -12.3115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8083  -13.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5177  -13.5373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5177  -11.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2271  -12.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2316  -13.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0109  -13.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4897  -12.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0037  -12.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0970  -13.5425    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.3887  -13.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6775  -13.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5177  -11.0734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9676  -13.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2569  -13.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2576  -14.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9750  -14.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6828  -14.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5511  -14.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8378  -14.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1276  -14.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1294  -15.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8474  -16.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5546  -15.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7099  -15.6103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9997  -16.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2862  -15.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5761  -16.0318    0.0000 N   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:

   

   ALA4081997

   ---

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: 456.59

Molecular Weight (Monoisotopic): 456.1290

AlogP: 2.45

#Rotatable Bonds: 8

Polar Surface Area: 117.94

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.64

CX Basic pKa: 9.11

CX LogP: 1.87

CX LogD: 1.60

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -1.56

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