2-Methyl-4-amine-5-((4-(((5-(2-amine-N-methyl-4-trifluoromethylthiazol)-1,3,4-oxadiazol-2-yl)thio)methyl)-4H-1,2,4-triazol-4-amine-2-yl)methyl)pyrimidine

ID: ALA3774501

PubChem CID: 127032966

Max Phase: Preclinical

Molecular Formula: C16H17F3N12S2

Molecular Weight: 498.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(C(F)(F)F)c(-c2nnc(SCc3cn(Cc4cnc(C)nc4N)nn3)n2N)s1

Standard InChI:  InChI=1S/C16H17F3N12S2/c1-7-23-3-8(12(20)24-7)4-30-5-9(26-29-30)6-32-15-28-27-13(31(15)21)10-11(16(17,18)19)25-14(22-2)33-10/h3,5H,4,6,21H2,1-2H3,(H,22,25)(H2,20,23,24)

Standard InChI Key:  WTFFBRCBPHWVMU-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 N   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
   -6.8247    9.8828    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1739   11.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6875   11.0329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4196    9.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    6.3997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0754    8.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8811   12.5550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0777    9.5622    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964    7.6980    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    8.3649    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2488   13.5749    0.0000 C   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  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  2  0
 18 27  1  0
 26 28  1  0
 24 29  1  0
 28 30  1  0
 28 31  1  0
 28 32  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3774501

   ---

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: 498.52

Molecular Weight (Monoisotopic): 498.1093

AlogP: 1.79

#Rotatable Bonds: 7

Polar Surface Area: 164.16

Molecular Species: NEUTRAL

HBA: 14

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.97

CX LogP: 0.98

CX LogD: 0.96

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: -2.27

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