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

ID: ALA3586169

PubChem CID: 122180148

Max Phase: Preclinical

Molecular Formula: C23H28N3O7P

Molecular Weight: 489.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H28N3O7P/c1-5-31-34(30,32-6-2)20-12-17(33-25(20)4)13-26-22(28)18-9-7-8-15-10-16(24-14(3)27)11-19(21(15)18)23(26)29/h7-11,17,20H,5-6,12-13H2,1-4H3,(H,24,27)/t17-,20+/m0/s1

Standard InChI Key:  VLZXYAAFBWJFCV-FXAWDEMLSA-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
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    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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   -1.3039    5.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    4.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    6.4602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3 15  1  0
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  6 16  1  1
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  5 15  1  6
 16  8  1  0
  8 11  1  0
  6  7  1  0
  2 13  1  0
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 12  1  1  0
 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
 27 18  2  0
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 18 23  1  0
 19 21  2  0
 28 29  1  0
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 27 21  1  0
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 20 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3586169

   ---

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: 489.47

Molecular Weight (Monoisotopic): 489.1665

AlogP: 3.62

#Rotatable Bonds: 8

Polar Surface Area: 114.48

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.85

CX Basic pKa: ┄

CX LogP: 1.60

CX LogD: 1.60

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -0.52

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