5-(3-(4-Bromophenyl)-5-methyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)-1,3,4-oxathiazol-2-one

ID: ALA4560024

PubChem CID: 155510481

Max Phase: Preclinical

Molecular Formula: C20H10BrNO5S

Molecular Weight: 456.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(-c2nsc(=O)o2)c(=O)oc2cc3occ(-c4ccc(Br)cc4)c3cc12

Standard InChI:  InChI=1S/C20H10BrNO5S/c1-9-12-6-13-14(10-2-4-11(21)5-3-10)8-25-15(13)7-16(12)26-19(23)17(9)18-22-28-20(24)27-18/h2-8H,1H3

Standard InChI Key:  JARUROUQWCSFLA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   28.7566   -6.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4622   -5.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4634   -4.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7548   -4.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0498   -4.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0485   -5.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2673   -5.9339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7856   -5.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2692   -4.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1747   -4.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8893   -4.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8882   -5.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1723   -6.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5945   -4.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3403   -4.7909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8886   -4.1850    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.4817   -3.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6820   -3.6443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1747   -3.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5947   -6.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8158   -2.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0184   -3.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5679   -3.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3172   -2.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5173   -2.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9687   -2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2224   -3.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2649   -1.4987    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  2  1  0
  3  4  2  0
  4  5  1  0
  6  5  2  0
  6  1  1  0
  7  6  1  0
  8  7  1  0
  9  8  2  0
  5  9  1  0
  3 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  1  0
  2 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 10 19  1  0
 12 20  2  0
 17 21  2  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  9 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560024

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.27

Molecular Weight (Monoisotopic): 454.9463

AlogP: 5.35

#Rotatable Bonds: 2

Polar Surface Area: 86.45

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.45

CX LogD: 5.45

Aromatic Rings: 5

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: -0.39

References

1. Schiffrer ES, Sosič I, Šterman A, Mravljak J, Raščan IM, Gobec S, Gobec M..  (2019)  A focused structure-activity relationship study of psoralen-based immunoproteasome inhibitors.,  10  (11): [PMID:32952997] [10.1039/C9MD00365G]

Source

Source(1):

• Scientific Literature