ID: ALA3144824

Max Phase: Preclinical

Molecular Formula: C21H26N4O

Molecular Weight: 350.47

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(C)nc(-n2[nH]c(C)c(Cc3ccc(C(C)(C)C)cc3)c2=O)n1

Standard InChI:  InChI=1S/C21H26N4O/c1-13-11-14(2)23-20(22-13)25-19(26)18(15(3)24-25)12-16-7-9-17(10-8-16)21(4,5)6/h7-11,24H,12H2,1-6H3

Standard InChI Key:  SEURGKCEJGDLPH-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: 350.47

Molecular Weight (Monoisotopic): 350.2107

AlogP: 3.77

#Rotatable Bonds: 3

Polar Surface Area: 63.57

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.48

CX Basic pKa: 4.10

CX LogP: 3.41

CX LogD: 2.60

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: -1.06

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

3. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]

Source

Source(3):

• GSK Malaria Screening
• St Jude Leishmania Screening
• Winzeler Lab Plasmodium Screening Data