1-{[4-(4-Fluorophenyl)-5-methoxycarbonyl-4-methyl-2-thiazol-2-yl-1H-pyrimidin-6-yl]methylmethylamino}cyclopropanecarboxylic Acid

ID: ALA4552222

PubChem CID: 71767036

Max Phase: Preclinical

Molecular Formula: C22H23FN4O4S

Molecular Weight: 458.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(CN(C)C2(C(=O)O)CC2)NC(c2nccs2)=NC1(C)c1ccc(F)cc1

Standard InChI:  InChI=1S/C22H23FN4O4S/c1-21(13-4-6-14(23)7-5-13)16(19(28)31-3)15(12-27(2)22(8-9-22)20(29)30)25-17(26-21)18-24-10-11-32-18/h4-7,10-11H,8-9,12H2,1-3H3,(H,25,26)(H,29,30)

Standard InChI Key:  DRGKTTMRTGHCOM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   11.3030   -9.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8271   -9.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5366  -10.2010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5366  -11.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8271  -11.4385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1176  -10.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4107   -9.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4107   -8.9729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6980  -10.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9911   -9.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4048  -11.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4048  -12.2497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1107  -12.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6953  -12.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8868  -12.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1667  -12.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9717  -13.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4434  -14.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763  -13.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2461  -11.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9968  -11.0949    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5430  -11.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1399  -12.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3360  -12.2488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3513   -9.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0686   -8.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6045   -7.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4115   -7.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6866   -8.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1624   -9.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9395   -7.2871    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
  5  4  1  0
  6  5  1  0
  7  6  2  0
  2  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 17 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
  4 21  1  0
 21 22  1  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 21 25  2  0
  2 26  1  0
 26 27  2  0
 28 27  1  0
 29 28  2  0
 30 29  1  0
 31 30  2  0
 26 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552222

   1-[[4-(4-fluorophenyl)-5-methoxycarbonyl-4-methyl-2-(1,3-thiazol-2-yl)-1H-pyrimidin-6-yl]methyl-methylamino]cyclopropane-1-carboxylic acid

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: 458.51

Molecular Weight (Monoisotopic): 458.1424

AlogP: 2.52

#Rotatable Bonds: 7

Polar Surface Area: 104.12

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.82

CX Basic pKa: 7.39

CX LogP: -0.18

CX LogD: -0.42

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.61

Np Likeness Score: -0.70

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