(15R)-2-[(1-aminoisoquinolin-6-yl)amino]-15-methyl-13-oxa-4,11-diazatricyclo[14.2.2.1(6,10)]henicosa-1(18),6,8,10(21),16,19-hexaene-3,12-dione

ID: ALA3808399

PubChem CID: 24873356

Max Phase: Preclinical

Molecular Formula: C28H27N5O3

Molecular Weight: 481.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1COC(=O)Nc2cccc(c2)CNC(=O)C(Nc2ccc3c(N)nccc3c2)c2ccc1cc2

Standard InChI:  InChI=1S/C28H27N5O3/c1-17-16-36-28(35)33-22-4-2-3-18(13-22)15-31-27(34)25(20-7-5-19(17)6-8-20)32-23-9-10-24-21(14-23)11-12-30-26(24)29/h2-14,17,25,32H,15-16H2,1H3,(H2,29,30)(H,31,34)(H,33,35)/t17-,25?/m0/s1

Standard InChI Key:  XQDFKGVDOCCXNS-LFUZPPSTSA-N

Molfile:  

     RDKit          2D

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   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
    9.2100    0.9900    0.0000 C   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
    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
    3.5800    2.1000    0.0000 N   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
    0.7200    1.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4900   -0.4100    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
    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
    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
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    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
    0.4074   -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
    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  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 22  1  0
 28 29  2  0
 29 19  1  0
 17 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33  2  1  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 12 36  2  0
 36  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3808399

   US9174974, Comparator 4

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: 481.56

Molecular Weight (Monoisotopic): 481.2114

AlogP: 4.95

#Rotatable Bonds: 2

Polar Surface Area: 118.37

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.52

CX Basic pKa: 9.17

CX LogP: 3.80

CX LogD: 2.49

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.32

Np Likeness Score: 0.62

References

1. Glunz PW, Mueller L, Cheney DL, Ladziata V, Zou Y, Wurtz NR, Wei A, Wong PC, Wexler RR, Priestley ES..  (2016)  Atropisomer Control in Macrocyclic Factor VIIa Inhibitors.,  59  (8): [PMID:27015008] [10.1021/acs.jmedchem.6b00244]

2.  (2015)  Macrocyclic factor VIIa inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database