3-amino-4-(5-chlorofuran-2-yl)-5,6,7,8,9,10-hexahydrocycloocta[b]thieno[3,2-e]pyridine-2-carboxamide

ID: ALA1094026

PubChem CID: 46884208

Max Phase: Preclinical

Molecular Formula: C18H18ClN3O2S

Molecular Weight: 375.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1sc2nc3c(c(-c4ccc(Cl)o4)c2c1N)CCCCCC3

Standard InChI:  InChI=1S/C18H18ClN3O2S/c19-12-8-7-11(24-12)13-9-5-3-1-2-4-6-10(9)22-18-14(13)15(20)16(25-18)17(21)23/h7-8H,1-6,20H2,(H2,21,23)

Standard InChI Key:  UECBTYORZJZSFP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -2.8298  -22.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8297  -21.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450  -21.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449  -23.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4175  -23.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4175  -21.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369  -21.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401  -22.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270  -23.1081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1248  -21.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5888  -21.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862  -22.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3766  -22.9587    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8677  -22.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807  -21.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381  -20.8289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6927  -22.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030  -23.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1073  -21.5765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253  -20.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5366  -20.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812  -19.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438  -19.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982  -20.1475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292  -18.6956    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  8  1  0
  7  6  1  0
  6  3  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  1  2  1  0
 15 16  1  0
  7  8  2  0
 14 17  1  0
  2  3  1  0
 17 18  2  0
  8  9  1  0
 17 19  1  0
  9 12  2  0
 10 20  1  0
 20 21  2  0
  1  4  1  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
  4  5  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094026

   6-Amino-8-(5-chlorofuran-2-yl)-4-thia-2-azatricyclo[7.6.0.03,7]pentadeca-1(9),2,5,7-tetraene-5-carboxamide

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: 375.88

Molecular Weight (Monoisotopic): 375.0808

AlogP: 4.55

#Rotatable Bonds: 2

Polar Surface Area: 95.14

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.05

CX LogD: 4.05

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.69

Np Likeness Score: -1.45

References

1. Lockman JW, Reeder MD, Suzuki K, Ostanin K, Hoff R, Bhoite L, Austin H, Baichwal V, Adam Willardsen J..  (2010)  Inhibition of eEF2-K by thieno[2,3-b]pyridine analogues.,  20  (7): [PMID:20189382] [10.1016/j.bmcl.2010.02.005]

Source

Source(1):

• Scientific Literature