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

ID: ALA3586170

PubChem CID: 122180149

Max Phase: Preclinical

Molecular Formula: C21H25N2O6P

Molecular Weight: 432.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)[C@@H]1C[C@H](CN2C(=O)c3cccc4cccc(c34)C2=O)ON1C

Standard InChI:  InChI=1S/C21H25N2O6P/c1-4-27-30(26,28-5-2)18-12-15(29-22(18)3)13-23-20(24)16-10-6-8-14-9-7-11-17(19(14)16)21(23)25/h6-11,15,18H,4-5,12-13H2,1-3H3/t15-,18-/m1/s1

Standard InChI Key:  QNNZWDYIGHBMGS-CRAIPNDOSA-N

Molfile:  

     RDKit          2D

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   -1.5832   -8.2191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9033   -3.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612   -6.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2847   -7.2455    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5914    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957   -3.4629    0.0000 O   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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 16  4  2  0
  5 14  1  0
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 21 24  1  0
 25 22  2  0
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  3 25  1  0
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 17  3  1  0
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 27 21  1  0
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 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3586170

   ---

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: 432.41

Molecular Weight (Monoisotopic): 432.1450

AlogP: 3.66

#Rotatable Bonds: 7

Polar Surface Area: 85.38

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: 2.27

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -0.19

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