5-methoxy-4-{3-[40-(2-dimethylaminoethoxy)-phenyl]acryolyl}benzo[d][1,3]oxathiol-2-one

ID: ALA243895

Chembl Id: CHEMBL243895

PubChem CID: 16724613

Max Phase: Preclinical

Molecular Formula: C21H21NO5S

Molecular Weight: 399.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2oc(=O)sc2c1C(=O)/C=C/c1ccc(OCCN(C)C)cc1

Standard InChI:  InChI=1S/C21H21NO5S/c1-22(2)12-13-26-15-7-4-14(5-8-15)6-9-16(23)19-17(25-3)10-11-18-20(19)28-21(24)27-18/h4-11H,12-13H2,1-3H3/b9-6+

Standard InChI Key:  MPGZLFODDCJQSG-RMKNXTFCSA-N

Alternative Forms

1. Parent:

   

   ALA243895

   4-[(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]prop-2-enoyl]-5-methoxy-1,3-benzoxathiol-2-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: 399.47

Molecular Weight (Monoisotopic): 399.1140

AlogP: 3.70

#Rotatable Bonds: 8

Polar Surface Area: 68.98

Molecular Species: BASE

HBA: 7

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.77

CX LogP: 3.98

CX LogD: 2.59

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -0.47

References

1. Konieczny MT, Konieczny W, Sabisz M, Skladanowski A, Wakieć R, Augustynowicz-Kopeć E, Zwolska Z..  (2007)  Acid-catalyzed synthesis of oxathiolone fused chalcones. Comparison of their activity toward various microorganisms and human cancer cells line.,  42  (5): [PMID:17300856] [10.1016/j.ejmech.2006.12.014]

2. Wang YH, Dong HH, Zhao F, Wang J, Yan F, Jiang YY, Jin YS..  (2016)  The synthesis and synergistic antifungal effects of chalcones against drug resistant Candida albicans.,  26  (13): [PMID:27210436] [10.1016/j.bmcl.2016.05.013]

3. Jin YS..  (2019)  Recent advances in natural antifungal flavonoids and their derivatives.,  29  (19): [PMID:31427220] [10.1016/j.bmcl.2019.07.048]

Source

Source(1):

• Scientific Literature