[2-amino-4-[[(1S)-1-(2-hydroxyethyl)butyl]amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-(2-methylthiazol-4-yl)methanone

ID: ALA4276988

PubChem CID: 71695973

Max Phase: Preclinical

Molecular Formula: C18H26N6O2S

Molecular Weight: 390.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@@H](CCO)Nc1nc(N)nc2c1CN(C(=O)c1csc(C)n1)CC2

Standard InChI:  InChI=1S/C18H26N6O2S/c1-3-4-12(6-8-25)21-16-13-9-24(7-5-14(13)22-18(19)23-16)17(26)15-10-27-11(2)20-15/h10,12,25H,3-9H2,1-2H3,(H3,19,21,22,23)/t12-/m0/s1

Standard InChI Key:  NGQVCINKVAWYDL-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

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   14.5253  -12.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9402  -11.9571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2315  -11.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9430  -12.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2298  -13.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2254  -14.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9324  -14.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6455  -14.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6517  -13.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2291  -10.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8174  -13.1886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1099  -12.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4020  -13.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6944  -12.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9866  -13.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9268  -15.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6317  -15.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2163  -15.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4747  -15.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9238  -15.9085    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.3275  -16.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1280  -16.4545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9901  -17.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1101  -11.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4026  -11.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4028  -10.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
 22 24  1  0
 13 25  1  1
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4276988

   [2-amino-4-[[(3S)-1-hydroxyhexan-3-yl]amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-(2-methyl-1,3-thiazol-4-yl)methanone

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: 390.51

Molecular Weight (Monoisotopic): 390.1838

AlogP: 1.99

#Rotatable Bonds: 7

Polar Surface Area: 117.26

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.54

CX LogP: 0.98

CX LogD: 0.92

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.23

References

1. McGowan DC, Herschke F, Khamlichi MD, Rosauro ML, Benedicto SMP, Pauwels F, Stoops B, Pande V, Scholliers A, Van Schoubroeck B, Mostmans W, Van Dijck K, Thoné T, Horton H, Fanning G, Jonckers THM, Raboisson P..  (2018)  Design and synthesis of tetrahydropyridopyrimidine based Toll-Like Receptor (TLR) 7/8 dual agonists.,  28  (19): [PMID:30143425] [10.1016/j.bmcl.2018.08.015]

Source

Source(1):

• Scientific Literature