2-Methyl-4-amine-5-((4-(((5-(3,5-dinitrophenyl)-1,3,4-oxadiazol-2-yl)thio)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-methylpyrimidine

ID: ALA3775862

PubChem CID: 127030526

Max Phase: Preclinical

Molecular Formula: C17H14N10O5S

Molecular Weight: 470.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncc(Cn2cc(CSc3nnc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)o3)nn2)c(N)n1

Standard InChI:  InChI=1S/C17H14N10O5S/c1-9-19-5-11(15(18)20-9)6-25-7-12(21-24-25)8-33-17-23-22-16(32-17)10-2-13(26(28)29)4-14(3-10)27(30)31/h2-5,7H,6,8H2,1H3,(H2,18,19,20)

Standard InChI Key:  XUUIACCQVRLQGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990   -0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2526   -1.3618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2524   -0.2436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0317    0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0997    2.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2115    3.6347    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8144    5.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0510    6.2856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0508    7.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4233    6.7985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2717    5.3062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7337    8.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3483    9.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1425   10.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3264   11.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7160   11.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9218    9.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533   11.4864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5903   12.6752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   10.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9024   12.1941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0135   11.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7399   13.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 28 29  2  0
 28 30  1  0
 24 28  1  0
 31 32  2  0
 31 33  1  0
 26 31  1  0
M  CHG  4  28   1  30  -1  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3775862

   ---

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: 470.43

Molecular Weight (Monoisotopic): 470.0869

AlogP: 2.17

#Rotatable Bonds: 8

Polar Surface Area: 207.71

Molecular Species: NEUTRAL

HBA: 14

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.97

CX LogP: 1.73

CX LogD: 1.72

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.22

Np Likeness Score: -1.97

References

1. He H, Wang W, Zhou Y, Xia Q, Ren Y, Feng J, Peng H, He H, Feng L..  (2016)  Rational design, synthesis and biological evaluation of 1,3,4-oxadiazole pyrimidine derivatives as novel pyruvate dehydrogenase complex E1 inhibitors.,  24  (8): [PMID:26972920] [10.1016/j.bmc.2016.03.011]

Source

Source(1):

• Scientific Literature