N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)hydrazinecarboxamide

ID: ALA3330915

PubChem CID: 118713312

Max Phase: Preclinical

Molecular Formula: C16H23N5O2

Molecular Weight: 317.39

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H23N5O2/c1-11(5-3-8-19-16(22)21-17)20-14-10-13(23-2)9-12-6-4-7-18-15(12)14/h4,6-7,9-11,20H,3,5,8,17H2,1-2H3,(H2,19,21,22)

Standard InChI Key:  LOXDHXLOSBFBHA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   10.8786  -19.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8786  -19.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6019  -20.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3210  -19.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3210  -19.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6019  -18.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6019  -17.7595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8786  -17.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0443  -20.2477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0443  -21.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3210  -21.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7263  -21.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4495  -21.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1688  -21.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8920  -21.0743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5740  -21.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2973  -21.0743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0164  -21.4710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5740  -22.3018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6019  -21.0743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8786  -21.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1966  -21.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1966  -20.2477    0.0000 C   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
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 10 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
 16 19  2  0
 20  3  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
  2 23  1  0
M  END

Alternative Forms

  1. Parent:

    ALA3330915

    ---

Associated Targets(Human)

CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW-620 (52400 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

L1210 (27553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Lipoxygenase (149 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium avium complex sp. (178 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium avium (4587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 317.39Molecular Weight (Monoisotopic): 317.1852AlogP: 2.00#Rotatable Bonds: 7
Polar Surface Area: 101.30Molecular Species: NEUTRALHBA: 5HBD: 4
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 12.76CX Basic pKa: 4.12CX LogP: 0.83CX LogD: 0.83
Aromatic Rings: 2Heavy Atoms: 23QED Weighted: 0.27Np Likeness Score: -1.04

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. 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