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

ID: ALA1091460

PubChem CID: 46884247

Max Phase: Preclinical

Molecular Formula: C20H23N3O2S

Molecular Weight: 369.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2c3c(nc4sc(C(N)=O)c(N)c24)CCCCCC3)oc1C

Standard InChI:  InChI=1S/C20H23N3O2S/c1-10-9-14(25-11(10)2)15-12-7-5-3-4-6-8-13(12)23-20-16(15)17(21)18(26-20)19(22)24/h9H,3-8,21H2,1-2H3,(H2,22,24)

Standard InChI Key:  AELMWZZFVUXOIB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   16.1952   -3.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1953   -2.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7800   -2.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7801   -4.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6075   -4.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6075   -2.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1881   -2.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1849   -3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8980   -4.0665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9002   -2.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6138   -2.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6112   -3.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4016   -3.9170    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.8927   -3.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4057   -2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6631   -1.7873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7177   -3.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1280   -3.9637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1323   -2.5348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8997   -1.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5616   -1.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3062   -0.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4812   -0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2268   -1.1058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9958    0.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7908    0.3472    0.0000 C   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
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091460

   6-Amino-8-(4,5-dimethylfuran-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: 369.49

Molecular Weight (Monoisotopic): 369.1511

AlogP: 4.51

#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: 4.44

CX LogD: 4.44

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -1.11

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