(S)-1-((3-(5-bromo-4-isopropyl-6-oxo-1,6-dihydropyrimidin-2-yl)-4-propoxyphenyl)sulfonyl)pyrrolidine-2-carboxylic acid

ID: ALA2414311

PubChem CID: 136244125

Max Phase: Preclinical

Molecular Formula: C21H26BrN3O6S

Molecular Weight: 528.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1ccc(S(=O)(=O)N2CCC[C@H]2C(=O)O)cc1-c1nc(C(C)C)c(Br)c(=O)[nH]1

Standard InChI:  InChI=1S/C21H26BrN3O6S/c1-4-10-31-16-8-7-13(32(29,30)25-9-5-6-15(25)21(27)28)11-14(16)19-23-18(12(2)3)17(22)20(26)24-19/h7-8,11-12,15H,4-6,9-10H2,1-3H3,(H,27,28)(H,23,24,26)/t15-/m0/s1

Standard InChI Key:  HIEBSPLRWFLZPT-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    4.7050  -20.6279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197  -19.8396    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1297  -20.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1049  -16.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1049  -17.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102  -17.7925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154  -17.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154  -16.5708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102  -16.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102  -15.3409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3960  -16.1643    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.2207  -17.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182  -18.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245  -19.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338  -18.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323  -17.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9255  -17.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244  -16.5723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6316  -16.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305  -15.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6298  -20.2516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377  -14.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978  -17.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6895  -17.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3990  -18.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7176  -21.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5204  -21.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324  -20.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3842  -19.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1104  -21.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3331  -21.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2804  -22.4138    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  2  0
  4  9  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  7 12  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14  2  1  0
  2 21  1  0
 20 22  1  0
  5 23  1  0
 23 24  1  0
 23 25  1  0
 21 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 21  1  0
 30 31  1  0
 30 32  2  0
 26 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2414311

   ---

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: 528.43

Molecular Weight (Monoisotopic): 527.0726

AlogP: 3.35

#Rotatable Bonds: 8

Polar Surface Area: 129.66

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.76

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: -0.80

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -1.12

References

1. Gong X, Wang G, Ren J, Liu Z, Wang Z, Chen T, Yang X, Jiang X, Shen J, Jiang H, Aisa HA, Xu Y, Li J..  (2013)  Exploration of the 5-bromopyrimidin-4(3H)-ones as potent inhibitors of PDE5.,  23  (17): [PMID:23867165] [10.1016/j.bmcl.2013.06.062]

Source

Source(1):

• Scientific Literature