Methyl 4-(4-Fluorophenyl)-4-methyl-6-(piperazin-1-ylmethyl)-2-thiazol-2-yl-1H-pyrimidine-5-carboxylate

ID: ALA4540158

PubChem CID: 155549697

Max Phase: Preclinical

Molecular Formula: C21H24FN5O2S

Molecular Weight: 429.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(CN2CCNCC2)NC(c2nccs2)=NC1(C)c1ccc(F)cc1

Standard InChI:  InChI=1S/C21H24FN5O2S/c1-21(14-3-5-15(22)6-4-14)17(20(28)29-2)16(13-27-10-7-23-8-11-27)25-18(26-21)19-24-9-12-30-19/h3-6,9,12,23H,7-8,10-11,13H2,1-2H3,(H,25,26)

Standard InChI Key:  JGNYPAWWISTLEA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.8927   -7.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4127   -7.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1222   -8.3969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1222   -9.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4127   -9.6303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7073   -9.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7073   -8.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0004   -7.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0004   -7.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2918   -8.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5891   -7.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9944   -9.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9944  -10.4374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7027  -10.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7027  -11.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9915  -12.0752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2874  -11.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2874  -10.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8275   -9.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5782   -9.2867    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1245   -9.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7172  -10.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9175  -10.4324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9369   -7.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6542   -6.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1860   -5.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9929   -6.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2681   -6.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7438   -7.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5210   -5.4912    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
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 13 18  1  0
  4 19  1  0
 19 20  1  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 19 23  2  0
  2 24  1  0
 24 25  2  0
 26 25  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 24 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540158

   ---

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: 429.52

Molecular Weight (Monoisotopic): 429.1635

AlogP: 1.88

#Rotatable Bonds: 5

Polar Surface Area: 78.85

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.21

CX LogP: 1.78

CX LogD: -0.02

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.71

Np Likeness Score: -1.11

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