ID: ALA455469

Max Phase: Preclinical

Molecular Formula: C16H11NO5

Molecular Weight: 297.27

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(/C=C/c1ccc2c(c1)OCO2)c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C16H11NO5/c18-14(12-2-1-3-13(9-12)17(19)20)6-4-11-5-7-15-16(8-11)22-10-21-15/h1-9H,10H2/b6-4+

Standard InChI Key:  MALGARLLWBWYQV-GQCTYLIASA-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: 297.27

Molecular Weight (Monoisotopic): 297.0637

AlogP: 3.22

#Rotatable Bonds: 4

Polar Surface Area: 78.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.45

CX LogD: 3.45

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.37

Np Likeness Score: -0.55

References

1. Chiaradia LD, Mascarello A, Purificação M, Vernal J, Cordeiro MN, Zenteno ME, Villarino A, Nunes RJ, Yunes RA, Terenzi H..  (2008)  Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA.,  18  (23): [PMID:18930396] [10.1016/j.bmcl.2008.09.105]

2. Chiaradia LD, Martins PG, Cordeiro MN, Guido RV, Ecco G, Andricopulo AD, Yunes RA, Vernal J, Nunes RJ, Terenzi H..  (2012)  Synthesis, biological evaluation, and molecular modeling of chalcone derivatives as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatases (PtpA and PtpB).,  55  (1): [PMID:22136336] [10.1021/jm2012062]

3. Martins PG, Menegatti AC, Chiaradia-Delatorre LD, de Oliveira KN, Guido RV, Andricopulo AD, Vernal J, Yunes RA, Nunes RJ, Terenzi H..  (2013)  Synthetic chalcones and sulfonamides as new classes of Yersinia enterocolitica YopH tyrosine phosphatase inhibitors.,  64  [PMID:23639652] [10.1016/j.ejmech.2013.04.018]

4. Monga V, Goyal K, Steindel M, Malhotra M, Rajani DP, Rajani SD.  (2013)  Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents,  [10.1007/s00044-013-0803-1]

Source

Source(1):

• Scientific Literature