Ethyl 3-bromo-4-(2-((2-chloro-9-(4-cyclopropyl-naphthalen-1-yl)-9H-purin-8-yl)thio)acetamido)benzoate

ID: ALA4483455

PubChem CID: 129908457

Max Phase: Preclinical

Molecular Formula: C29H23BrClN5O3S

Molecular Weight: 636.96

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(NC(=O)CSc2nc3cnc(Cl)nc3n2-c2ccc(C3CC3)c3ccccc23)c(Br)c1

Standard InChI:  InChI=1S/C29H23BrClN5O3S/c1-2-39-27(38)17-9-11-22(21(30)13-17)33-25(37)15-40-29-34-23-14-32-28(31)35-26(23)36(29)24-12-10-18(16-7-8-16)19-5-3-4-6-20(19)24/h3-6,9-14,16H,2,7-8,15H2,1H3,(H,33,37)

Standard InChI Key:  HVAOHEUHWCFVCL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   13.0143  -12.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2259  -13.1572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2573  -11.7397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0741  -11.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5002  -11.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3171  -11.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7077  -11.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2857  -12.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4648  -12.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881  -13.1178    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3115  -12.4237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7713  -13.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2795  -13.7456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5077  -13.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7881  -13.8655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0902  -13.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1119  -12.6225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8275  -12.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5254  -12.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5096  -14.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3056  -14.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5398  -15.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9782  -16.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1823  -15.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6206  -16.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8288  -16.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5945  -15.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1562  -14.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9480  -15.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2125  -16.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8068  -17.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0207  -17.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3747  -13.8342    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.1099  -10.3456    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.5247  -11.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9176  -12.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9488  -11.1203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4935  -13.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8864  -13.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
  4  5  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 12 20  1  0
 15 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 21 30  2  0
 25 30  1  0
 31 32  1  0
 32 33  1  0
 31 33  1  0
 24 31  1  0
 14 21  1  0
 17 34  1  0
 11 13  1  0
  2 11  1  0
  6 35  1  0
  8 36  1  0
 36 37  1  0
 36 38  2  0
 37 39  1  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483455

   ---

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: 636.96

Molecular Weight (Monoisotopic): 635.0394

AlogP: 7.17

#Rotatable Bonds: 8

Polar Surface Area: 99.00

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.12

CX Basic pKa: ┄

CX LogP: 7.31

CX LogD: 7.31

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.11

Np Likeness Score: -1.48

References

1. Lu X, Li X, Yang J, Huang B, Kang D, Zhao F, Zhou Z, De Clercq E, Daelemans D, Pannecouque C, Zhan P, Liu X..  (2016)  Arylazolyl(azinyl)thioacetanilides. Part 20: Discovery of novel purinylthioacetanilides derivatives as potent HIV-1 NNRTIs via a structure-based bioisosterism approach.,  24  (18): [PMID:27501911] [10.1016/j.bmc.2016.07.041]

Source

Source(1):

• Scientific Literature