1-((4-Chlorophenyl)(phenyl)methyl)-3-(4-((6-methoxyquinolin-8-yl)amino)pentyl)urea

ID: ALA3330910

PubChem CID: 118713307

Max Phase: Preclinical

Molecular Formula: C29H31ClN4O2

Molecular Weight: 503.05

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCNC(=O)NC(c2ccccc2)c2ccc(Cl)cc2)c2ncccc2c1

Standard InChI:  InChI=1S/C29H31ClN4O2/c1-20(33-26-19-25(36-2)18-23-11-7-16-31-28(23)26)8-6-17-32-29(35)34-27(21-9-4-3-5-10-21)22-12-14-24(30)15-13-22/h3-5,7,9-16,18-20,27,33H,6,8,17H2,1-2H3,(H2,32,34,35)

Standard InChI Key:  LKYQNUHVCKULNM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.6727   -2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9435   -3.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2185   -2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5352   -3.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9435   -3.9094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3518   -3.0844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0810   -2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.8059   -3.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5351   -2.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2143   -3.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9435   -2.6510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6727   -3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3976   -2.6010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0767   -3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8059   -2.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5351   -3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2142   -2.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2142   -1.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5351   -1.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8059   -1.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9434   -1.3885    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.0767   -3.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3518   -4.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3518   -5.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.8059   -4.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6727   -3.8635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9435   -0.6094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2185   -0.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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 33 28  1  0
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  1 35  1  0
 35 36  1  0
M  END

Alternative Forms

  1. Parent:

    ALA3330910

    ---

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
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L6 (7924 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: 503.05Molecular Weight (Monoisotopic): 502.2136AlogP: 6.57#Rotatable Bonds: 10
Polar Surface Area: 75.28Molecular Species: NEUTRALHBA: 4HBD: 3
#RO5 Violations: 2HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski): 2
CX Acidic pKa: CX Basic pKa: 4.08CX LogP: 5.46CX LogD: 5.46
Aromatic Rings: 4Heavy Atoms: 36QED Weighted: 0.21Np Likeness Score: -1.13

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