methyl 5-(3-amino-2-carbamoyl-5,6,7,8,9,10-hexahydrocycloocta[b]thieno[3,2-e]pyridin-4-yl)-3-methylfuran-2-carboxylate

ID: ALA1089712

PubChem CID: 46884248

Max Phase: Preclinical

Molecular Formula: C21H23N3O4S

Molecular Weight: 413.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1oc(-c2c3c(nc4sc(C(N)=O)c(N)c24)CCCCCC3)cc1C

Standard InChI:  InChI=1S/C21H23N3O4S/c1-10-9-13(28-17(10)21(26)27-2)14-11-7-5-3-4-6-8-12(11)24-20-15(14)16(22)18(29-20)19(23)25/h9H,3-8,22H2,1-2H3,(H2,23,25)

Standard InChI Key:  ZRQQPRIJTHNAKJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -3.6757  -10.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756   -9.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0908   -9.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0907  -11.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633  -11.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -9.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828   -9.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859  -10.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729  -10.9956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -9.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2570   -9.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596  -10.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307  -10.8462    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0218  -10.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5349   -9.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -8.7164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8468  -10.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571  -10.8929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2615   -9.4640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9711   -8.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3092   -8.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5646   -7.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897   -7.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6440   -8.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0801   -6.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8779   -6.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428   -5.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6983   -6.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1837   -5.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 22 25  1  0
  5  8  1  0
  7  6  1  0
  6  3  1  0
 26 27  2  0
 26 28  1  0
 23 26  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089712

   Methyl 5-(6-amino-5-carbamoyl-4-thia-2-azatricyclo[7.6.0.03,7]pentadeca-1(9),2,5,7-tetraen-8-yl)-3-methylfuran-2-carboxylate

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: 413.50

Molecular Weight (Monoisotopic): 413.1409

AlogP: 3.99

#Rotatable Bonds: 3

Polar Surface Area: 121.44

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -1.00

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