US9034866, 456

ID: ALA3696728

PubChem CID: 89755164

Max Phase: Preclinical

Molecular Formula: C18H16F2N2O4S

Molecular Weight: 394.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC[C@](C)(O)C#Cc1ccc2c(c1)-c1nc(C(N)=O)sc1C(F)(F)CO2

Standard InChI:  InChI=1S/C18H16F2N2O4S/c1-17(24,8-25-2)6-5-10-3-4-12-11(7-10)13-14(18(19,20)9-26-12)27-16(22-13)15(21)23/h3-4,7,24H,8-9H2,1-2H3,(H2,21,23)/t17-/m1/s1

Standard InChI Key:  DXCOIQUGCMYDKA-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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    7.6459   -9.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4594   -8.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9111   -7.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4272   -7.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6787   -8.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1757   -6.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789   -5.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306   -4.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7822   -3.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7175   -2.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695   -0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    1.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4548    0.6059    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370    2.2584    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0899   -0.9120    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0226   -2.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5767   -2.8095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1920   -3.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0115   -4.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3099   -2.9106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  6
  4  6  1  0
  4  7  1  0
  7  8  3  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  2  0
 22 23  1  0
 23 12  1  0
 23 24  2  0
 24  9  1  0
 20 25  1  0
 25 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3696728

   4,4-difluoro-9-[(3R)-3-hydroxy-4-methoxy-3-methylbut-1-ynyl]-5H-[1]benzoxepino[5,4-d][1,3]thiazole-2-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: 394.40

Molecular Weight (Monoisotopic): 394.0799

AlogP: 2.14

#Rotatable Bonds: 3

Polar Surface Area: 94.67

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.56

CX Basic pKa: ┄

CX LogP: 2.32

CX LogD: 2.32

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -0.47

References

1.  (2015)  Tricyclic compounds and methods of use therefor, 

Source

Source(1):

• BindingDB Database