4-(4-Fluorophenyl)-4-methyl-6-(morpholinomethyl)-2-thiazol-2-yl-1H-pyrimidine-5-carboxylic Acid

ID: ALA4520466

PubChem CID: 155542275

Max Phase: Preclinical

Molecular Formula: C20H21FN4O3S

Molecular Weight: 416.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(c2ccc(F)cc2)N=C(c2nccs2)NC(CN2CCOCC2)=C1C(=O)O

Standard InChI:  InChI=1S/C20H21FN4O3S/c1-20(13-2-4-14(21)5-3-13)16(19(26)27)15(12-25-7-9-28-10-8-25)23-17(24-20)18-22-6-11-29-18/h2-6,11H,7-10,12H2,1H3,(H,23,24)(H,26,27)

Standard InChI Key:  KVUKEXLKJJBZDL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   11.4343   -9.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1397  -10.2824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1397  -11.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4343  -11.5158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7248  -11.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7248  -10.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0220   -9.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3134  -10.2794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0220   -9.0584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0160  -11.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0160  -12.3229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3054  -12.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3054  -13.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0091  -13.9609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7238  -13.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7238  -12.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8492  -11.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5957  -11.1723    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.1419  -11.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7387  -12.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9391  -12.3179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9584   -9.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6758   -8.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2076   -7.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0145   -8.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2896   -8.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7654   -9.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5385   -7.3768    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  2  0
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  7  6  2  0
  2  7  1  0
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  8  9  2  0
  8 10  1  0
  6 11  1  0
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 12 17  1  0
  4 18  1  0
 18 19  1  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 18 22  2  0
  2 23  1  0
 23 24  2  0
 25 24  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 23 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4520466

   ---

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: 416.48

Molecular Weight (Monoisotopic): 416.1318

AlogP: 2.22

#Rotatable Bonds: 5

Polar Surface Area: 87.05

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.26

CX Basic pKa: 5.55

CX LogP: -0.41

CX LogD: -1.66

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.78

Np Likeness Score: -1.17

References

1. Qiu Z, Lin X, Zhou M, Liu Y, Zhu W, Chen W, Zhang W, Guo L, Liu H, Wu G, Huang M, Jiang M, Xu Z, Zhou Z, Qin N, Ren S, Qiu H, Zhong S, Zhang Y, Zhang Y, Wu X, Shi L, Shen F, Mao Y, Zhou X, Yang W, Wu JZ, Yang G, Mayweg AV, Shen HC, Tang G..  (2016)  Design and Synthesis of Orally Bioavailable 4-Methyl Heteroaryldihydropyrimidine Based Hepatitis B Virus (HBV) Capsid Inhibitors.,  59  (16): [PMID:27458651] [10.1021/acs.jmedchem.6b00879]

Source

Source(1):

• Scientific Literature