2-(5,7-dimethyl-9H-[1,2,4]triazino[6,5-b]indol-3-ylthio)-N-(thiophen-2-ylmethyl)acetamide

ID: ALA521390

PubChem CID: 20967209

Max Phase: Preclinical

Molecular Formula: C18H17N5OS2

Molecular Weight: 383.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c2c(c1)[nH]c1nnc(SCC(=O)NCc3cccs3)nc12

Standard InChI:  InChI=1S/C18H17N5OS2/c1-10-6-11(2)15-13(7-10)20-17-16(15)21-18(23-22-17)26-9-14(24)19-8-12-4-3-5-25-12/h3-7H,8-9H2,1-2H3,(H,19,24)(H,20,22)

Standard InChI Key:  OSJRUUBDPBOLBK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.2458   -8.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338   -8.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8218   -7.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172   -8.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0303   -8.5728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0376   -7.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473   -7.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332   -7.8056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029   -7.0513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8932   -6.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -6.4811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9597   -8.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -5.6328    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2561   -5.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5856   -4.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4054   -4.6909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954   -4.1201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -5.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7154   -5.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2728   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0238   -5.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310   -4.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -4.5392    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  1  4  2  0
  4 14  1  0
  6  7  1  0
  2 15  1  0
  7  9  1  0
 12 16  1  0
  8  5  1  0
 16 17  1  0
  8  9  2  0
 17 18  1  0
  2  3  2  0
 18 19  1  0
  3  6  1  0
 18 20  2  0
  5  4  1  0
 19 21  1  0
  5  6  2  0
 21 22  1  0
 22 23  2  0
  1  2  1  0
  8 13  1  0
  9 10  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA521390

   2-[(5,7-dimethyl-9H-[1,2,4]triazino[6,5-b]indol-3-yl)sulfanyl]-N-(thiophen-2-ylmethyl)acetamide

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: 383.50

Molecular Weight (Monoisotopic): 383.0875

AlogP: 3.59

#Rotatable Bonds: 5

Polar Surface Area: 83.56

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.75

CX Basic pKa: 0.09

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -2.25

References

1. Yu WM, Guvench O, Mackerell AD, Qu CK..  (2008)  Identification of small molecular weight inhibitors of Src homology 2 domain-containing tyrosine phosphatase 2 (SHP-2) via in silico database screening combined with experimental assay.,  51  (23): [PMID:19007293] [10.1021/jm800229d]

2. Shen D, Chen W, Zhu J, Wu G, Shen R, Xi M, Sun H..  (2020)  Therapeutic potential of targeting SHP2 in human developmental disorders and cancers.,  190  [PMID:32061959] [10.1016/j.ejmech.2020.112117]

Source

Source(1):

• Scientific Literature