2-(1-Amino-isoquinolin-6-ylamino)-13-oxa-4,11-diaza-tricyclo[14.2.2.1(6,10)]henicosa-1(19),6(21),7,9,16(20),17-hexaene-3,12-dione

ID: ALA3809472

PubChem CID: 57842742

Max Phase: Preclinical

Molecular Formula: C27H25N5O3

Molecular Weight: 467.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nccc2cc(NC3C(=O)NCc4cccc(c4)NC(=O)OCCc4ccc3cc4)ccc12

Standard InChI:  InChI=1S/C27H25N5O3/c28-25-23-9-8-22(15-20(23)10-12-29-25)31-24-19-6-4-17(5-7-19)11-13-35-27(34)32-21-3-1-2-18(14-21)16-30-26(24)33/h1-10,12,14-15,24,31H,11,13,16H2,(H2,28,29)(H,30,33)(H,32,34)

Standard InChI Key:  AHEIEXXGHCSZMY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.9416   -7.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683   -6.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6508   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790   -6.9392    0.0000 C   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
    4.3163   -4.7114    0.0000 N   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
    5.5700   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
   -0.4900    0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
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    3.1500   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    1.7057   -4.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958   -5.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867   -4.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1967   -5.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2241   -6.8437    0.0000 N   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
    7.1600    2.1000    0.0000 O   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
    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
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 13 14  2  0
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 16 17  1  0
 17 18  1  0
  8 18  1  0
 18 19  2  0
 15 20  2  0
 20 21  1  0
 21 22  2  0
 13 22  1  0
 12 23  1  0
 23 24  2  0
  9 24  1  0
  6 25  2  0
 25 26  1  0
  3 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
  2 29  1  0
 21 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 12 34  1  0
 34 35  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3809472

   2-[(1-Aminoisoquinolin-6-yl)amino]-13-oxa-4,11-diazatricyclo[14.2.2.16,10]henicosa-1(19),6(21),7,9,16(20),17-hexaene-3,12-dione

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: 467.53

Molecular Weight (Monoisotopic): 467.1957

AlogP: 4.39

#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: 12.50

CX Basic pKa: 9.17

CX LogP: 3.44

CX LogD: 2.12

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.35

Np Likeness Score: 0.68

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]

Source

Source(1):

• Scientific Literature