ID: ALA537336

Max Phase: Preclinical

Molecular Formula: C20H24Cl2N2O

Molecular Weight: 379.33

Molecule Type: Small molecule

Representations

Synonyms (3): TCMDC-125673 | GNF-Pf-4508 | TCMDC-125673
Synonyms from Alternative Forms(3):

Canonical SMILES:  CC(C)CCNCC(O)Cn1c2ccc(Cl)cc2c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C20H24Cl2N2O/c1-13(2)7-8-23-11-16(25)12-24-19-5-3-14(21)9-17(19)18-10-15(22)4-6-20(18)24/h3-6,9-10,13,16,23,25H,7-8,11-12H2,1-2H3

Standard InChI Key:  UFYSTLUSQSQEBD-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: 379.33

Molecular Weight (Monoisotopic): 378.1266

AlogP: 5.10

#Rotatable Bonds: 7

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: 10.05

CX LogP: 5.14

CX LogD: 2.59

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -0.69

References

1. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

2. 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]

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. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

5. 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]

Source

Source(4):

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