3-amino-1-{[4-({[[(aminocarbonothioyl)amino](iminio)methyl]amino}methyl)-2,5-dimethylbenzyl]amino}-3-thioxopropan-1-iminium

ID: ALA1160541

PubChem CID: 44462181

Max Phase: Preclinical

Molecular Formula: C15H23N7S2

Molecular Weight: 365.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(CNC(=N)/N=C(/N)S)c(C)cc1CNC(=N)CC(=N)S

Standard InChI:  InChI=1S/C15H23N7S2/c1-8-4-11(7-21-14(18)22-15(19)24)9(2)3-10(8)6-20-12(16)5-13(17)23/h3-4H,5-7H2,1-2H3,(H2,16,20)(H2,17,23)(H5,18,19,21,22,24)

Standard InChI Key:  ZYYUJOQYDCDOIK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -0.8625    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625    1.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500    1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833    0.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -3.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792    0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500    0.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    1.5125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -1.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375   -0.5417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500    2.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -0.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875    1.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  2  0
  5 17  1  0
  6  5  2  0
  7  5  1  0
  8 12  1  0
  9 19  1  0
 10  7  1  0
 11  9  2  0
 12 14  2  0
 13 11  1  0
 14  9  1  0
 15  1  1  0
 16  3  1  0
 17 20  1  0
 18 10  1  0
 19 15  1  0
 20  8  1  0
 21  3  1  0
 22 10  2  0
 23 14  1  0
 24 13  1  0
  8 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160541

   3-Amino-3-[[4-[[[amino-(carbamothioylamino)methylidene]amino]methyl]-2,5-dimethylphenyl]methylimino]propanethioamide

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: 365.53

Molecular Weight (Monoisotopic): 365.1456

AlogP: 1.94

#Rotatable Bonds: 6

Polar Surface Area: 133.99

Molecular Species: ZWITTERION

HBA: 3

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.44

CX Basic pKa: 15.00

CX LogP: 3.01

CX LogD: 0.61

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.22

Np Likeness Score: -0.37

References

1. Zolli-Juran M, Cechetto JD, Hartlen R, Daigle DM, Brown ED..  (2003)  High throughput screening identifies novel inhibitors of Escherichia coli dihydrofolate reductase that are competitive with dihydrofolate.,  13  (15): [PMID:12852950] [10.1016/s0960-894x(03)00480-3]

Source

Source(1):

• Scientific Literature