(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(4-nitrophenyl)prop-2-en-1-one

ID: ALA455453

Chembl Id: CHEMBL455453

Cas Number: 92858-63-4

PubChem CID: 5382771

Max Phase: Preclinical

Molecular Formula: C16H11NO5

Molecular Weight: 297.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc2c(c1)OCO2)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C16H11NO5/c18-14(12-3-5-13(6-4-12)17(19)20)7-1-11-2-8-15-16(9-11)22-10-21-15/h1-9H,10H2/b7-1+

Standard InChI Key:  FMNQGVMNCNMWBE-LREOWRDNSA-N

Alternative Forms

1. Parent:

   

   ALA455453

   (E)-3-(1,3-benzodioxol-5-yl)-1-(4-nitrophenyl)prop-2-en-1-one

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

Calculated 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: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

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: -0.40

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. Gomes KS, da Costa-Silva TA, Oliveira IH, Aguilar AM, Oliveira-Silva D, Uemi M, Silva WA, Melo LR, Andrade CKZ, Tempone AG, Tempone AG, Baldim JL, Lago JHG..  (2019)  Structure-activity relationship study of antitrypanosomal chalcone derivatives using multivariate analysis.,  29  (12): [PMID:31000155] [10.1016/j.bmcl.2019.04.020]

Source

Source(1):

• Scientific Literature