Diethyl trans-5-(5-nitro-1,3-dioxo-2,3-dihydro-1H-benzo[de]izochinolin-2-ylmethyl)-2-methylisoxazolidin-3-yl-3-phosphonate

ID: ALA3586167

PubChem CID: 122180146

Max Phase: Preclinical

Molecular Formula: C21H24N3O8P

Molecular Weight: 477.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)[C@@H]1C[C@@H](CN2C(=O)c3cccc4cc([N+](=O)[O-])cc(c34)C2=O)ON1C

Standard InChI:  InChI=1S/C21H24N3O8P/c1-4-30-33(29,31-5-2)18-11-15(32-22(18)3)12-23-20(25)16-8-6-7-13-9-14(24(27)28)10-17(19(13)16)21(23)26/h6-10,15,18H,4-5,11-12H2,1-3H3/t15-,18+/m0/s1

Standard InChI Key:  LTSOQADXCXTLJJ-MAUKXSAKSA-N

Molfile:  

     RDKit          2D

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   -0.7915   -7.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914   -1.4965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5914   -1.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -2.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0432    5.1102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3 15  1  0
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  7  5  1  0
  6 16  1  1
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 16  8  1  0
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  6  7  1  0
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 16  4  2  0
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 13  9  1  0
 30 17  1  0
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  3 25  1  0
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 24 28  2  0
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 29 30  2  0
 27 21  1  0
 17 26  2  0
 27 30  1  0
 31 32  2  0
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M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3586167

   ---

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: 477.41

Molecular Weight (Monoisotopic): 477.1301

AlogP: 3.57

#Rotatable Bonds: 8

Polar Surface Area: 128.52

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.24

Np Likeness Score: -0.50

References

1. Kokosza K, Andrei G, Schols D, Snoeck R, Piotrowska DG..  (2015)  Design, antiviral and cytostatic properties of isoxazolidine-containing amonafide analogues.,  23  (13): [PMID:26001344] [10.1016/j.bmc.2015.04.079]

Source

Source(1):

• Scientific Literature