(6S,11aS,11bS)-3-((2,4-dinitrophenyl)(hydroxy)methyl)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one

ID: ALA5274280

Max Phase: Preclinical

Molecular Formula: C20H19N3O7

Molecular Weight: 413.39

Names and Identifiers

Canonical SMILES:  O=C1O[C@@]23C[C@@H](C=CC2=C1C(O)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-])N1CCCC[C@H]13

Standard InChI:  InChI=1S/C20H19N3O7/c24-18(13-6-4-11(22(26)27)9-15(13)23(28)29)17-14-7-5-12-10-20(14,30-19(17)25)16-3-1-2-8-21(12)16/h4-7,9,12,16,18,24H,1-3,8,10H2/t12-,16+,18?,20+/m1/s1

Standard InChI Key:  MXNOARXDOFVDKT-GBZRXNQRSA-N

Molfile:  

 
     RDKit          2D

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    0.8188   -0.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -1.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697   -0.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0588    0.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2333    0.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    1.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2333    1.7946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3336    2.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5472    1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973    1.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0047    1.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2123   -1.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2123   -2.1323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4059   -1.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2240    0.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970   -0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5819   -1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669   -0.7912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669    0.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669    0.8600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5819    0.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970    0.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696   -1.7783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2950   -1.7783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568   -2.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    1.0795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0588    1.7944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970    1.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  1  6  1  0
  5  6  2  0
  6  7  1  0
  8  7  1  0
  9 10  2  0
 11 10  1  0
  7 12  1  0
 10 12  1  0
 13 14  1  6
 15 13  1  0
 13 16  1  0
 16 17  2  0
 12 18  2  0
 17 18  1  0
 11 19  1  0
 18 19  1  0
 19 15  1  6
 20 21  1  0
 13 22  1  0
 21 22  1  0
 19 23  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 20 26  1  0
 25 26  1  0
  3 27  1  0
 27 28  2  0
 27 29  1  0
  5 30  1  0
 30 31  1  0
 30 32  2  0
M  CHG  4  27   1  29  -1  30   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5274280

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 413.39

Molecular Weight (Monoisotopic): 413.1223

AlogP: 2.33

#Rotatable Bonds: 4

Polar Surface Area: 136.05

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.80

CX Basic pKa: 8.95

CX LogP: 2.18

CX LogD: 0.63

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: 0.97

References

1. Xu XL, Lan JX, Huang H, Dai W, Peng XP, Liu SL, Chen WM, Huang LJ, Liu J, Li XJ, Zeng JL, Huang XH, Zhao GN, Hou W..  (2023)  Synthesis, biological activity and mechanism of action of novel allosecurinine derivatives as potential antitumor agents.,  82  [PMID:36906964] [10.1016/j.bmc.2023.117234]

Source

Source(1):

• Scientific Literature