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

ID: ALA1091459

PubChem CID: 46884246

Max Phase: Preclinical

Molecular Formula: C19H21N3O3S

Molecular Weight: 371.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H21N3O3S/c20-16-15-14(13-8-7-10(9-23)25-13)11-5-3-1-2-4-6-12(11)22-19(15)26-17(16)18(21)24/h7-8,23H,1-6,9,20H2,(H2,21,24)

Standard InChI Key:  TYPCRWZOLZGKDS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    5.7702   -2.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7703   -2.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550   -1.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3551   -3.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1825   -3.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1825   -1.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7631   -2.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7599   -2.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4730   -3.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4752   -1.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1888   -2.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1862   -3.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9766   -3.2628    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4677   -2.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9807   -1.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2381   -1.1331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2927   -2.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7030   -3.3096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7073   -1.8806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4747   -0.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1366   -0.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8812    0.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0562    0.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8018   -0.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5708    1.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9059    1.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  5  8  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091459

   6-Amino-8-[5-(hydroxymethyl)furan-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: 371.46

Molecular Weight (Monoisotopic): 371.1304

AlogP: 3.39

#Rotatable Bonds: 3

Polar Surface Area: 115.37

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.74

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: -1.09

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