N1-(1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)-N2-(4-((6-methoxyquinolin-8-yl)amino)pentyl)hydrazine-1,2-dicarboxamide

ID: ALA3330908

PubChem CID: 118713305

Max Phase: Preclinical

Molecular Formula: C21H32N6O6

Molecular Weight: 464.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCNC(=O)NNC(=O)NC(CO)(CO)CO)c2ncccc2c1

Standard InChI:  InChI=1S/C21H32N6O6/c1-14(24-17-10-16(33-2)9-15-6-4-7-22-18(15)17)5-3-8-23-19(31)26-27-20(32)25-21(11-28,12-29)13-30/h4,6-7,9-10,14,24,28-30H,3,5,8,11-13H2,1-2H3,(H2,23,26,31)(H2,25,27,32)

Standard InChI Key:  MXZOJEIJAFOJRL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    6.2978  -21.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2978  -22.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9784  -23.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7084  -22.5839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7084  -21.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9784  -21.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9784  -20.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7084  -20.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4344  -20.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4344  -21.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1645  -21.7548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8450  -21.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5752  -21.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3052  -21.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0353  -21.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7159  -21.3672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4419  -21.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1719  -21.3672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8525  -21.7548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5826  -21.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3126  -21.7548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0386  -21.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5826  -20.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4419  -22.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8450  -20.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7084  -19.2759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9784  -18.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7321  -21.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0656  -20.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4524  -21.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7404  -20.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3722  -20.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7333  -20.1370    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
  5  6  2  0
  6  1  1  0
  7  6  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 17 24  2  0
 12 25  1  0
  8 26  1  0
 26 27  1  0
 22 28  1  0
 22 29  1  0
 28 30  1  0
 22 31  1  0
 29 32  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3330908

   ---

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: 464.52

Molecular Weight (Monoisotopic): 464.2383

AlogP: 0.05

#Rotatable Bonds: 11

Polar Surface Area: 177.10

Molecular Species: NEUTRAL

HBA: 8

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.84

CX Basic pKa: 4.06

CX LogP: -1.66

CX LogD: -1.66

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.17

Np Likeness Score: -0.78

References

1. Pavić K, Perković I, Cindrić M, Pranjić M, Martin-Kleiner I, Kralj M, Schols D, Hadjipavlou-Litina D, Katsori AM, Zorc B..  (2014)  Novel semicarbazides and ureas of primaquine with bulky aryl or hydroxyalkyl substituents: synthesis, cytostatic and antioxidative activity.,  86  [PMID:25203780] [10.1016/j.ejmech.2014.09.013]

2. Levatić J, Pavić K, Perković I, Uzelac L, Ester K, Kralj M, Kaiser M, Rottmann M, Supek F, Zorc B..  (2018)  Machine learning prioritizes synthesis of primaquine ureidoamides with high antimalarial activity and attenuated cytotoxicity.,  146  [PMID:29407988] [10.1016/j.ejmech.2018.01.062]

Source

Source(1):

• Scientific Literature