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

ID: ALA3586172

PubChem CID: 122180151

Max Phase: Preclinical

Molecular Formula: C21H26N3O6P

Molecular Weight: 447.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H26N3O6P/c1-4-28-31(27,29-5-2)18-11-15(30-23(18)3)12-24-20(25)16-8-6-7-13-9-14(22)10-17(19(13)16)21(24)26/h6-10,15,18H,4-5,11-12,22H2,1-3H3/t15-,18-/m1/s1

Standard InChI Key:  PKMGLHDTGOTPMT-CRAIPNDOSA-N

Molfile:  

     RDKit          2D

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   -5.3699   -6.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -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
   -2.6927   -4.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9003   -8.6142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2804   -8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158  -10.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0236   -9.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6612   -6.0252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864   -8.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1197   -4.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950   -2.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847   -7.2455    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2957    2.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957    0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6307    0.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957    2.2447    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
   -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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000    4.2112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3 15  1  0
 14 12  1  0
 11 10  1  0
  7  5  1  0
  6 16  1  1
 16  2  1  0
  5 15  1  1
 16  8  1  0
  8 11  1  0
  6  7  1  0
  2 13  1  0
 12  6  1  0
 12  1  1  0
 16  4  2  0
  5 14  1  0
 13  9  1  0
 30 17  1  0
 21 24  1  0
 25 22  2  0
 20 19  1  0
  3 25  1  0
 25 18  1  0
 24 28  2  0
 17  3  1  0
 27 18  2  0
 23 20  2  0
 18 23  1  0
 19 21  2  0
 28 29  1  0
 29 30  2  0
 27 21  1  0
 17 26  2  0
 27 30  1  0
 20 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3586172

   ---

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: 447.43

Molecular Weight (Monoisotopic): 447.1559

AlogP: 3.25

#Rotatable Bonds: 7

Polar Surface Area: 111.40

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.76

CX LogP: 1.49

CX LogD: 1.49

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: -0.18

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