1-(3-amino-benzo[d]isoxazol-5-yl)-6-(2'-dimethylaminomethyl-biphenyl-4-yl)-3,5-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one

ID: ALA213865

PubChem CID: 16046152

Max Phase: Preclinical

Molecular Formula: C29H27N7O2

Molecular Weight: 505.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nn(-c2ccc3onc(N)c3c2)c2c(=O)n(-c3ccc(-c4ccccc4CN(C)C)cc3)c(C)nc12

Standard InChI:  InChI=1S/C29H27N7O2/c1-17-26-27(36(32-17)22-13-14-25-24(15-22)28(30)33-38-25)29(37)35(18(2)31-26)21-11-9-19(10-12-21)23-8-6-5-7-20(23)16-34(3)4/h5-15H,16H2,1-4H3,(H2,30,33)

Standard InChI Key:  HSCKUOWMBQOWFF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.8854   -4.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -4.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -4.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067   -3.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3221   -3.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928   -5.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940   -6.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6734   -3.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4187   -3.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6144   -3.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3236   -2.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1273   -2.4331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578   -4.7819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903   -2.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0651   -4.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2384   -5.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0237   -5.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6362   -4.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583   -4.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6734   -3.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4967   -3.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1069   -2.4804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8935   -2.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301   -1.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 17 18  1  0
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  4  5  2  0
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  2  3  2  0
 21 22  2  0
 10 11  1  0
 22 23  1  0
 23  1  1  0
 11  8  2  0
  1 24  1  0
  5  6  1  0
 24 25  2  0
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  1  2  1  0
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  6  7  2  0
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 16 17  1  0
 32 33  2  0
 33 28  1  0
  5 28  1  0
  7  2  1  0
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  3  4  1  0
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  8  9  1  0
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M  END

Alternative Forms

1. Alternative Forms:

   

   ALA213865

   1-(3-Amino-1,2-benzoxazol-5-yl)-6-[4-[2-[(dimethylamino)methyl]phenyl]phenyl]-3,5-dimethylpyrazolo[4,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid

2. Parent:

   

   ALA213865

   1-(3-amino-1,2-benzoxazol-5-yl)-6-(4-{2-[(dimethylamino)methyl]phenyl}phenyl)-3,5-dimethyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one

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: 505.58

Molecular Weight (Monoisotopic): 505.2226

AlogP: 4.64

#Rotatable Bonds: 5

Polar Surface Area: 108.00

Molecular Species: BASE

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.34

CX LogP: 3.53

CX LogD: 1.60

Aromatic Rings: 6

Heavy Atoms: 38

QED Weighted: 0.36

Np Likeness Score: -1.37

References

1. Li YL, Fevig JM, Cacciola J, Buriak J, Rossi KA, Jona J, Knabb RM, Luettgen JM, Wong PC, Bai SA, Wexler RR, Lam PY..  (2006)  Preparation of 1-(3-aminobenzo[d]isoxazol-5-yl)-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-ones as potent, selective, and efficacious inhibitors of coagulation factor Xa.,  16  (19): [PMID:16870435] [10.1016/j.bmcl.2006.07.002]

Source

Source(1):

• Scientific Literature