US9174974, Example 33

ID: ALA3977297

PubChem CID: 118098775

Max Phase: Preclinical

Molecular Formula: C33H36FN5O5

Molecular Weight: 601.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2ccc1[C@@H](C)COC(=O)Nc1cc(F)c(O[C@@H](C)CO)c(c1)CN(C)C(=O)[C@@H]2Nc1ccc2c(N)nccc2c1

Standard InChI:  InChI=1S/C33H36FN5O5/c1-18-11-22-5-7-26(18)19(2)17-43-33(42)38-25-13-23(30(28(34)14-25)44-20(3)16-40)15-39(4)32(41)29(22)37-24-6-8-27-21(12-24)9-10-36-31(27)35/h5-14,19-20,29,37,40H,15-17H2,1-4H3,(H2,35,36)(H,38,42)/t19-,20-,29+/m0/s1

Standard InChI Key:  NINDJBINKRLZFB-QWQFASRJSA-N

Molfile:  

     RDKit          2D

 44 48  0  0  1  0  0  0  0  0999 V2000
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   -1.5276    1.5928    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200    1.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9300    0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800    2.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3200    1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052   -0.1699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1600    2.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2100    0.9900    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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    5.5700   -2.5000    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
    6.7800   -0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3400   -3.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3224   -4.7115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6127   -5.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5973   -6.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8885   -7.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1952   -7.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4865   -7.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4741   -8.9682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7932   -7.0317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8087   -5.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5175   -4.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2108   -5.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9195   -4.7416    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
    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
    0.7200   -2.5000    0.0000 C   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
    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
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
 21 25  1  0
 25 26  1  1
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 30  1  0
 36 37  2  0
 37 27  1  0
 25 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 43  6  1  0
 43 44  2  0
 44 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3977297

   US9174974, Example 33

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: 601.68

Molecular Weight (Monoisotopic): 601.2700

AlogP: 5.50

#Rotatable Bonds: 5

Polar Surface Area: 139.04

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.81

CX Basic pKa: 9.17

CX LogP: 4.25

CX LogD: 2.94

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.24

Np Likeness Score: 0.17

References

1.  (2015)  Macrocyclic factor VIIa inhibitors, 

Source

Source(1):

• BindingDB Database