2-amino-N-ethyl-3-(3,4,5-trimethoxybenzoyl)-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carbothioamide

ID: ALA522049

PubChem CID: 44580467

Max Phase: Preclinical

Molecular Formula: C20H25N3O4S2

Molecular Weight: 435.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=S)N1CCc2c(sc(N)c2C(=O)c2cc(OC)c(OC)c(OC)c2)C1

Standard InChI:  InChI=1S/C20H25N3O4S2/c1-5-22-20(28)23-7-6-12-15(10-23)29-19(21)16(12)17(24)11-8-13(25-2)18(27-4)14(9-11)26-3/h8-9H,5-7,10,21H2,1-4H3,(H,22,28)

Standard InChI Key:  VZIYFIWZMRZRBB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.5840  -17.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5674  -19.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7370  -19.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360  -18.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525  -16.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040  -16.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2341  -17.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7155  -20.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111  -19.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728  -21.8648    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5320  -20.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9339  -20.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0953  -21.1841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733  -21.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4414  -21.4624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8768  -21.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4965  -20.9037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0387  -22.2573    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3346  -20.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543  -19.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0
 13 15  2  0
 14 19  1  0
  3  4  2  0
  2  8  1  0
 18 16  1  0
 16 17  1  0
 17 14  2  0
 18 19  2  0
  3  9  1  0
  4  5  1  0
  9 10  1  0
  2  3  1  0
  8 11  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  5  6  2  0
 17 24  1  0
  7 12  1  0
 22 25  1  0
  6  1  1  0
 25 26  1  0
  5 13  1  0
 25 27  2  0
  1  2  2  0
 26 28  1  0
 13 14  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA522049

   2-amino-N-ethyl-3-(3,4,5-trimethoxybenzoyl)-5,7-dihydro-4H-thieno[2,3-c]pyridine-6-carbothioamide

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: 435.57

Molecular Weight (Monoisotopic): 435.1286

AlogP: 2.84

#Rotatable Bonds: 6

Polar Surface Area: 86.05

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.95

References

1. Romagnoli R, Baraldi PG, Carrion MD, Cruz-Lopez O, Cara CL, Tolomeo M, Grimaudo S, Di Cristina A, Pipitone MR, Balzarini J, Kandil S, Brancale A, Sarkar T, Hamel E..  (2008)  Synthesis and biological evaluation of 2-amino-3-(3',4',5'-trimethoxybenzoyl)-6-substituted-4,5,6,7-tetrahydrothieno[2,3-c]pyridine derivatives as antimitotic agents and inhibitors of tubulin polymerization.,  18  (18): [PMID:18725179] [10.1016/j.bmcl.2008.08.006]

Source

Source(1):

• Scientific Literature