ID: ALA580701

Max Phase: Preclinical

Molecular Formula: C21H24Cl2N2O

Molecular Weight: 391.34

Molecule Type: Small molecule

Representations

Synonyms (2): GNF-Pf-5053 | SJ000110999
Synonyms from Alternative Forms(2):

Canonical SMILES:  OC(CNC1CCCCC1)Cn1c2ccc(Cl)cc2c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C21H24Cl2N2O/c22-14-6-8-20-18(10-14)19-11-15(23)7-9-21(19)25(20)13-17(26)12-24-16-4-2-1-3-5-16/h6-11,16-17,24,26H,1-5,12-13H2

Standard InChI Key:  JAEHRJLXQLQEPU-UHFFFAOYSA-N

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

Properties

Molecular Weight: 391.34

Molecular Weight (Monoisotopic): 390.1266

AlogP: 5.38

#Rotatable Bonds: 5

Polar Surface Area: 37.19

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 10.21

CX LogP: 5.33

CX LogD: 2.65

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -0.72

References

1. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

2. Guiguemde WA, Shelat AA, Bouck D, Duffy S, Crowther GJ, Davis PH, Smithson DC, Connelly M, Clark J, Zhu F, Jiménez-Díaz MB, Martinez MS, Wilson EB, Tripathi AK, Gut J, Sharlow ER, Bathurst I, El Mazouni F, Fowble JW, Forquer I, McGinley PL, Castro S, Angulo-Barturen I, Ferrer S, Rosenthal PJ, Derisi JL, Sullivan DJ, Lazo JS, Roos DS, Riscoe MK, Phillips MA, Rathod PK, Van Voorhis WC, Avery VM, Guy RK..  (2010)  Chemical genetics of Plasmodium falciparum.,  465  (7296): [PMID:20485428] [10.1038/nature09099]

3. Meister S, Plouffe DM, Kuhen KL, Bonamy GM, Wu T, Barnes SW, Bopp SE, Borboa R, Bright AT, Che J, Cohen S, Dharia NV, Gagaring K, Gettayacamin M, Gordon P, Groessl T, Kato N, Lee MC, McNamara CW, Fidock DA, Nagle A, Nam TG, Richmond W, Roland J, Rottmann M, Zhou B, Froissard P, Glynne RJ, Mazier D, Sattabongkot J, Schultz PG, Tuntland T, Walker JR, Zhou Y, Chatterjee A, Diagana TT, Winzeler EA..  (2011)  Imaging of Plasmodium liver stages to drive next-generation antimalarial drug discovery.,  334  (6061): [PMID:22096101] [10.1126/science.1211936]

4. Hurley KA, Heinrich VA, Hershfield JR, Demons ST, Weibel DB..  (2015)  Membrane-Targeting DCAP Analogues with Broad-Spectrum Antibiotic Activity against Pathogenic Bacteria.,  6  (4): [PMID:25941556] [10.1021/acsmedchemlett.5b00024]

5. Wang T, Mäser P, Picard D..  (2016)  Inhibition of Plasmodium falciparum Hsp90 Contributes to the Antimalarial Activities of Aminoalcohol-carbazoles.,  59  (13): [PMID:27312008] [10.1021/acs.jmedchem.6b00591]

Source

Source(3):

• Scientific Literature
• Novartis Malaria Screening
• St Jude Malaria Screening