2-(Bis(4-methoxyphenyl)methylene)-N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)hydrazinecarboxamide

ID: ALA3330912

PubChem CID: 118713309

Max Phase: Preclinical

Molecular Formula: C31H35N5O4

Molecular Weight: 541.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=NNC(=O)NCCCC(C)Nc2cc(OC)cc3cccnc23)c2ccc(OC)cc2)cc1

Standard InChI:  InChI=1S/C31H35N5O4/c1-21(34-28-20-27(40-4)19-24-8-6-17-32-30(24)28)7-5-18-33-31(37)36-35-29(22-9-13-25(38-2)14-10-22)23-11-15-26(39-3)16-12-23/h6,8-17,19-21,34H,5,7,18H2,1-4H3,(H2,33,36,37)

Standard InChI Key:  VXHLPWUSNYOETR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.9791  -11.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7040  -11.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.3831  -11.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.6539  -10.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0622  -11.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7873  -11.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.2456   -7.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.5164   -8.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2456   -6.7677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.1123  -11.2800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
  2  3  1  0
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  4  5  1  0
  5  6  2  0
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  9  8  1  0
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  4 10  1  0
  3 11  1  0
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 15 16  1  0
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 18 19  1  0
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 20 21  2  0
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 22 23  2  0
 23 24  1  0
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 25 28  1  0
 28 29  1  0
 21 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 33 36  1  0
 36 37  1  0
 18 38  2  0
  1 39  1  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3330912

   ---

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: 541.65

Molecular Weight (Monoisotopic): 541.2689

AlogP: 5.59

#Rotatable Bonds: 12

Polar Surface Area: 106.10

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.70

CX Basic pKa: 4.08

CX LogP: 4.70

CX LogD: 4.70

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.12

Np Likeness Score: -0.75

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]

3. Pavić K, Perković I, Pospíšilová Š, Machado M, Fontinha D, Prudêncio M, Jampilek J, Coffey A, Endersen L, Rimac H, Zorc B..  (2018)  Primaquine hybrids as promising antimycobacterial and antimalarial agents.,  143  [PMID:29220797] [10.1016/j.ejmech.2017.11.083]

Source

Source(1):

• Scientific Literature