3-amino-4-(furan-2-yl)-5,6,7,8,9,10,11,12-octahydrocyclodeca[e]thieno[2,3-b]pyridine-2-carboxamide

ID: ALA1093095

PubChem CID: 46884287

Max Phase: Preclinical

Molecular Formula: C20H23N3O2S

Molecular Weight: 369.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1sc2nc3c(c(-c4ccco4)c2c1N)CCCCCCCC3

Standard InChI:  InChI=1S/C20H23N3O2S/c21-17-16-15(14-10-7-11-25-14)12-8-5-3-1-2-4-6-9-13(12)23-20(16)26-18(17)19(22)24/h7,10-11H,1-6,8-9,21H2,(H2,22,24)

Standard InChI Key:  ZQGFAHWTQSCDJF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.5771  -17.0956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5793  -15.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2930  -15.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2904  -16.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0807  -16.9462    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5718  -16.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0849  -15.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3422  -14.8164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3968  -16.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8071  -16.9929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8115  -15.5640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5789  -14.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408  -14.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9854  -13.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1603  -13.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060  -14.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1430  -17.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1475  -17.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8608  -16.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8653  -15.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1544  -15.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4388  -15.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4366  -16.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7210  -17.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7211  -17.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4321  -18.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
 12 13  2  0
  2 20  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
  7  3  1  0
  3  4  1  0
  7  8  1  0
 19  1  1  0
  6  9  1  0
  1  4  2  0
  9 10  2  0
  9 11  1  0
  3  2  2  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 18 19  1  0
 24 25  1  0
 25 26  1  0
 26 17  1  0
 24 23  1  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093095

   15-Amino-17-(furan-2-yl)-13-thia-11-azatricyclo[8.7.0.012,16]heptadeca-1(10),11,14,16-tetraene-14-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: 369.49

Molecular Weight (Monoisotopic): 369.1511

AlogP: 4.68

#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: 4.62

CX LogD: 4.62

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -1.47

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