ID: ALA229141

Max Phase: Preclinical

Molecular Formula: C16H13N5O3S

Molecular Weight: 355.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1ccc(NC(=S)N/N=C2\C(=O)Nc3ccc([N+](=O)[O-])cc32)cc1

Standard InChI:  InChI=1S/C16H13N5O3S/c1-9-2-4-10(5-3-9)17-16(25)20-19-14-12-8-11(21(23)24)6-7-13(12)18-15(14)22/h2-8H,1H3,(H2,17,20,25)(H,18,19,22)

Standard InChI Key:  GXMRGBYLRDNPLA-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: 355.38

Molecular Weight (Monoisotopic): 355.0739

AlogP: 2.55

#Rotatable Bonds: 3

Polar Surface Area: 108.66

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.37

CX Basic pKa:

CX LogP: 3.63

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: -2.00

References

1. Karali N, Gürsoy A, Kandemirli F, Shvets N, Kaynak FB, Ozbey S, Kovalishyn V, Dimoglo A..  (2007)  Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives.,  15  (17): [PMID:17561405] [10.1016/j.bmc.2007.05.063]

2. Pervez H, Manzoor N, Yaqub M, Nasim F, Khan KM.  (2012)  Synthesis and biological evaluation of some N4-substituted 5-nitroisatin-3-thiosemicarbazones,  21  (9): [10.1007/s00044-011-9745-7]

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(2):

• Scientific Literature
• Winzeler Lab Plasmodium Screening Data