ID: ALA2098229

Max Phase: Preclinical

Molecular Formula: C17H22N2O

Molecular Weight: 270.38

Molecule Type: Small molecule

Representations

Synonyms (2): TCMDC-142501 | GSK346583A
Synonyms from Alternative Forms(2):

Canonical SMILES:  Cc1cc(C)c2cc(C(=O)NC3CCCCC3)[nH]c2c1

Standard InChI:  InChI=1S/C17H22N2O/c1-11-8-12(2)14-10-16(19-15(14)9-11)17(20)18-13-6-4-3-5-7-13/h8-10,13,19H,3-7H2,1-2H3,(H,18,20)

Standard InChI Key:  HVSCDVSEALONKG-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: 270.38

Molecular Weight (Monoisotopic): 270.1732

AlogP: 3.85

#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: 3.89

CX LogD: 3.89

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.86

Np Likeness Score: -1.05

References

1. Ballell, L., Bates, R. H., Young, R. J., Alvarez-Gomez, D., Alvarez-Ruiz, E., Barroso, V., Blanco, D., Crespo, B., Escribano, J., Gonzalez, R., Lozano, S., Huss, S., Santos-Villarejo, A., Martin-Plaza, J. J., Mendoza, A., Rebollo-Lopez, M. J., Remuinan-Blanco, M., Lavandera, J. L., Perez-Herran, E., Gamo-Benito, F. J., Garcia-Bustos, J. F., Barros, D., Castro, J. P. and Cammack, N. GSK Tuberculosis Screening Data,  [10.6019/CHEMBL2095176]

2. 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]

3. Kondreddi RR, Jiricek J, Rao SP, Lakshminarayana SB, Camacho LR, Rao R, Herve M, Bifani P, Ma NL, Kuhen K, Goh A, Chatterjee AK, Dick T, Diagana TT, Manjunatha UH, Smith PW..  (2013)  Design, synthesis, and biological evaluation of indole-2-carboxamides: a promising class of antituberculosis agents.,  56  (21): [PMID:24090347] [10.1021/jm4012774]

4. Manjunatha UH, Smith PW..  (2015)  Perspective: Challenges and opportunities in TB drug discovery from phenotypic screening.,  23  (16): [PMID:25577708] [10.1016/j.bmc.2014.12.031]

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. 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(2):

• Scientific Literature
• GSK Tuberculosis Screening