N-(3-(5,6-Diethyl-4(3H)-pyrimidone-2-yl)-4-n-propoxyphenyl)sulfonyl-L-proline

ID: ALA4539785

PubChem CID: 137051684

Max Phase: Preclinical

Molecular Formula: C22H29N3O6S

Molecular Weight: 463.56

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H29N3O6S/c1-4-12-31-19-10-9-14(32(29,30)25-11-7-8-18(25)22(27)28)13-16(19)20-23-17(6-3)15(5-2)21(26)24-20/h9-10,13,18H,4-8,11-12H2,1-3H3,(H,27,28)(H,23,24,26)/t18-/m0/s1

Standard InChI Key:  LQCPQKMDKUNQLG-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   30.4589   -6.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8717   -5.6956    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.0541   -5.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0431   -2.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0420   -3.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7500   -3.6594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4597   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4568   -2.4273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7482   -2.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7458   -1.2049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3353   -2.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3351   -1.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3339   -3.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6265   -3.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1645   -3.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1644   -4.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.8680   -3.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8645   -2.4303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5704   -2.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2799   -2.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9858   -2.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5810   -6.1074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6679   -6.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4698   -7.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8816   -6.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3342   -5.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5047   -4.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2821   -4.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8978   -4.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  5  2  0
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  9 10  2  0
  4 11  1  0
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  5 13  1  0
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  7 15  1  0
 20 21  1  0
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 22 23  1  0
 23 24  1  0
 17  2  1  0
  2 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
 29 30  1  6
 30 31  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539785

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 463.56

Molecular Weight (Monoisotopic): 463.1777

AlogP: 2.59

#Rotatable Bonds: 9

Polar Surface Area: 129.66

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.76

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: -0.81

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: -1.16

References

1. Wang Z, Jiang X, Zhang X, Tian G, Yang R, Wu J, Zou X, Liu Z, Yang X, Wu C, Shi J, Li J, Suo J, Wang Y, Zhang R, Xu Z, Gong X, He Y, Zhu W, Aisa HA, Jiang H, Xu Y, Shen J..  (2019)  Pharmacokinetics-Driven Optimization of 4(3 H)-Pyrimidinones as Phosphodiesterase Type 5 Inhibitors Leading to TPN171, a Clinical Candidate for the Treatment of Pulmonary Arterial Hypertension.,  62  (10): [PMID:31021628] [10.1021/acs.jmedchem.9b00123]

Source

Source(1):

• Scientific Literature