US9174974, Example 10

ID: ALA3979309

PubChem CID: 118098649

Max Phase: Preclinical

Molecular Formula: C34H34F3N5O5

Molecular Weight: 649.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2ccc1[C@@H](C)COC(=O)Nc1ccc([C@@H](CC(F)F)C(=O)O)c(c1)CN(C)C(=O)[C@@H]2Nc1ccc2c(N)ncc(F)c2c1

Standard InChI:  InChI=1S/C34H34F3N5O5/c1-17-10-19-4-7-23(17)18(2)16-47-34(46)41-21-5-8-24(27(33(44)45)13-29(36)37)20(11-21)15-42(3)32(43)30(19)40-22-6-9-25-26(12-22)28(35)14-39-31(25)38/h4-12,14,18,27,29-30,40H,13,15-16H2,1-3H3,(H2,38,39)(H,41,46)(H,44,45)/t18-,27+,30+/m0/s1

Standard InChI Key:  VORDOLJPJWNPOM-GJABKNSGSA-N

Molfile:  

     RDKit          2D

 47 51  0  0  1  0  0  0  0  0999 V2000
   10.2495   -1.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2100   -0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7922   -1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0909   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3922   -1.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -0.5521    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3943   -2.3536    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917   -2.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7527   -3.2594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310   -3.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -1.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9300   -3.2100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9278   -4.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -1.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3400   -3.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3163   -4.7114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0052   -5.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6674   -7.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815   -6.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9303   -7.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9510   -8.8241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2162   -6.8520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903   -5.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8785   -4.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8578   -3.4249    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074   -5.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192   -4.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5700   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7800   -3.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0000   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0000   -1.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7800   -0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7779    0.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5700   -1.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9300   -0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  6
 13 14  1  0
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  2  0
 17 19  1  0
 11 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  1
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 31  1  0
 38 39  2  0
 39 28  1  0
 26 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  2  0
 43  2  1  0
 43 44  1  0
 44 45  1  0
 44 46  2  0
 46 40  1  0
 20 47  2  0
 47  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3979309

   US9174974, Example 10

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: 649.67

Molecular Weight (Monoisotopic): 649.2512

AlogP: 6.57

#Rotatable Bonds: 6

Polar Surface Area: 146.88

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.17

CX Basic pKa: 7.53

CX LogP: 3.09

CX LogD: 2.85

Aromatic Rings: 4

Heavy Atoms: 47

QED Weighted: 0.18

Np Likeness Score: 0.00

References

1.  (2015)  Macrocyclic factor VIIa inhibitors, 

Source

Source(1):

• BindingDB Database