ID: ALA2347950

Max Phase: Preclinical

Molecular Formula: C19H26N2O

Molecular Weight: 298.43

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(C)c2cc(C(=O)NC3CCCCCCC3)[nH]c2c1

Standard InChI:  InChI=1S/C19H26N2O/c1-13-10-14(2)16-12-18(21-17(16)11-13)19(22)20-15-8-6-4-3-5-7-9-15/h10-12,15,21H,3-9H2,1-2H3,(H,20,22)

Standard InChI Key:  YTDHMGDEWFURLB-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 298.43

Molecular Weight (Monoisotopic): 298.2045

AlogP: 4.63

#Rotatable Bonds: 2

Polar Surface Area: 44.89

Molecular Species: NEUTRAL

HBA: 1

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: -0.95

References

1. Onajole OK, Pieroni M, Tipparaju SK, Lun S, Stec J, Chen G, Gunosewoyo H, Guo H, Ammerman NC, Bishai WR, Kozikowski AP..  (2013)  Preliminary structure-activity relationships and biological evaluation of novel antitubercular indolecarboxamide derivatives against drug-susceptible and drug-resistant Mycobacterium tuberculosis strains.,  56  (10): [PMID:23611124] [10.1021/jm4003878]

2. MMV Pathogen Box,  [10.6019/CHEMBL3637841]

3. Nathan group, Weill Cornell Medical College; Barry Lab, NIAID NIH; Winzeler lab, UCSD; Laboratory of Microbiology, Parasitology and Hygiene (LMPH), Univ. of Antwerp; London School of Hygiene and Tropical Medicine; Parasite Chemotherapy Unit at Swiss Tropical and Public Health Institute; Huston group at the University of Vermont; Castellanos group at UTMB, Galveston, Texas; Sakanari Lab, Univ. of Calif. San Francisco; Townson (Simon) Lab, Imperial College London; Fidelis Cho-Ngwa Lab, University of Buea, Buea, Cameroon; Laboratory of Molecular Parasitology at the New York Blood Center; Bickle Lab, London School of Hygiene and Tropical Medicine; Keiser Lab, Swiss Tropical and Public Health Institute; Caffrey group at the Center for Discovery and Innovation in Parasitic Diseases, Skaggs School of Pharmacy and Pharmaceutical Sciences, UC San Diego; University of Cape Town; Shanmugam group at CSIR-National Chemical Laboratory, Pune (India); Novartis Institute for Tropical Disease-Singapore; Abbvie. MMV Pathogen Box Bioactivity Data,  [10.6019/CHEMBL3832761]

4. Anna Ehmann. The Australian National University Dept Of Immunology Pathogen Box Compounds Screened,  [10.6019/CHEMBL3987221]

5. Franz ND, Belardinelli JM, Kaminski MA, Dunn LC, Calado Nogueira de Moura V, Blaha MA, Truong DD, Li W, Jackson M, North EJ..  (2017)  Design, synthesis and evaluation of indole-2-carboxamides with pan anti-mycobacterial activity.,  25  (14): [PMID:28545813] [10.1016/j.bmc.2017.05.015]

6. Stec J, Onajole OK, Lun S, Guo H, Merenbloom B, Vistoli G, Bishai WR, Kozikowski AP..  (2016)  Indole-2-carboxamide-based MmpL3 Inhibitors Show Exceptional Antitubercular Activity in an Animal Model of Tuberculosis Infection.,  59  (13): [PMID:27275668] [10.1021/acs.jmedchem.6b00415]

7. Sarink, M; Mykytyn, A; Tielens, A; van Hellemond, J. Naegleria gruberi Pathogen Box compounds screening,  [10.6019/CHEMBL4513101]

8. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - MMV compounds,  [10.6019/CHEMBL4513149]

9. Tan YJ, Li M, Gunawan GA, Nyantakyi SA, Dick T, Go ML, Lam Y..  (2021)  Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility.,  12  (5.0): [PMID:34055215] [10.1021/acsmedchemlett.0c00588]

10. Kumar G, Kapoor S..  (2023)  Targeting mycobacterial membranes and membrane proteins: Progress and limitations.,  81  [PMID:36804747] [10.1016/j.bmc.2023.117212]

Source

Source(3):

• Scientific Literature
• MMV Pathogen Box
• CO-ADD antimicrobial screening data