Ethyl 1-allyl-2'-amino-1'-(isonicotinamido)-6,7',7'-trimethyl-2,5'-dioxo-1,1',2,4',5',6',7',8'-octahydro-3,4'-biquinoline-3'-carboxylate

ID: ALA2402128

PubChem CID: 71739715

Max Phase: Preclinical

Molecular Formula: C33H35N5O5

Molecular Weight: 581.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCn1c(=O)c(C2C(C(=O)OCC)=C(N)N(NC(=O)c3ccncc3)C3=C2C(=O)CC(C)(C)C3)cc2cc(C)ccc21

Standard InChI:  InChI=1S/C33H35N5O5/c1-6-14-37-23-9-8-19(3)15-21(23)16-22(31(37)41)26-27-24(17-33(4,5)18-25(27)39)38(29(34)28(26)32(42)43-7-2)36-30(40)20-10-12-35-13-11-20/h6,8-13,15-16,26H,1,7,14,17-18,34H2,2-5H3,(H,36,40)

Standard InChI Key:  MPENGEYHCDBKNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 43 47  0  0  0  0  0  0  0  0999 V2000
   12.2072  -15.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2060  -16.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6345  -15.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9191  -14.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6373  -16.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9200  -16.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9185  -17.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6334  -17.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3515  -17.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3495  -16.4383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0634  -16.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7785  -16.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4925  -16.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0668  -17.6728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6541  -18.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6448  -20.6035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3611  -20.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3649  -19.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9321  -20.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9373  -19.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2299  -18.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5169  -19.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5157  -20.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2236  -20.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0797  -18.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7938  -19.3656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0753  -18.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5086  -18.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6415  -21.4284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3544  -21.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3512  -22.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0705  -21.4341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6336  -23.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6301  -23.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3435  -24.3155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0620  -23.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0620  -23.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0741  -20.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2343  -18.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2228  -19.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6877  -20.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0961  -20.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4926  -14.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  9 14  2  0
  8 15  1  0
 15 20  1  0
 15 18  1  0
 19 16  1  0
 16 17  1  0
 17 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
 18 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 16 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 31 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 31  1  0
 17 38  1  0
 21 39  2  0
 28 40  1  0
 23 41  1  0
 23 42  1  0
  1 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2402128

   ethyl 4-(1-allyl-6-methyl-2-oxo-3-quinolyl)-2-amino-7,7-dimethyl-5-oxo-1-(pyridine-4-carbonylamino)-6,8-dihydro-4H-quinoline-3-carboxylate

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: 581.67

Molecular Weight (Monoisotopic): 581.2638

AlogP: 4.01

#Rotatable Bonds: 7

Polar Surface Area: 136.62

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.07

CX Basic pKa: 3.17

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.32

Np Likeness Score: -0.98

References

1. Jardosh HH, Patel MP..  (2013)  Design and synthesis of biquinolone-isoniazid hybrids as a new class of antitubercular and antimicrobial agents.,  65  [PMID:23747804] [10.1016/j.ejmech.2013.05.003]

Source

Source(1):

• Scientific Literature