US9034866, 437

ID: ALA3696718

PubChem CID: 89754668

Max Phase: Preclinical

Molecular Formula: C20H18FN3O5S

Molecular Weight: 431.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@@](O)(C#Cc2cc3c(cc2F)OC[C@@](C)(O)c2sc(C(N)=O)nc2-3)C1=O

Standard InChI:  InChI=1S/C20H18FN3O5S/c1-19(27)9-29-13-8-12(21)10(3-4-20(28)5-6-24(2)18(20)26)7-11(13)14-15(19)30-17(23-14)16(22)25/h7-8,27-28H,5-6,9H2,1-2H3,(H2,22,25)/t19-,20+/m1/s1

Standard InChI Key:  IEYNPJLLDVCWGR-UXHICEINSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  1  0  0  0  0  0999 V2000
   11.8700   -0.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6785   -0.1584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6593    0.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2976    0.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5218   -1.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7866   -2.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0877   -0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6535   -0.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194    0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1198   -0.8265    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 O   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
   -1.6852   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0042   -1.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4746    0.5191    0.0000 O   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
   -1.2135   -2.9844    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135   -2.9844    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
    0.0031   -5.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -5.9628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0350   -5.9661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4522    2.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856    1.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7653    2.4724    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9467   -1.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4309   -2.5658    0.0000 O   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  0
  5  6  1  1
  5  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  1
 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 11  1  0
 22 18  2  0
 20 23  1  0
 23 24  2  0
 23 25  1  0
 12 26  1  0
 26 27  2  0
 27  9  1  0
 27 28  1  0
  5 29  1  0
 29  2  1  0
 29 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3696718

   (4R)-8-fluoro-4-hydroxy-9-[2-[(3R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl]ethynyl]-4-methyl-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: 431.45

Molecular Weight (Monoisotopic): 431.0951

AlogP: 0.59

#Rotatable Bonds: 1

Polar Surface Area: 125.98

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.02

CX Basic pKa: ┄

CX LogP: 0.41

CX LogD: 0.41

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -0.19

References

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

Source

Source(1):

• BindingDB Database