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

ID: ALA4483550

PubChem CID: 155540804

Max Phase: Preclinical

Molecular Formula: C20H10FNO5S

Molecular Weight: 395.37

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H10FNO5S/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:  WOSWSUPINGDEAI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.9743  -13.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6799  -13.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6811  -12.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9725  -12.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2675  -12.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2662  -13.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4850  -13.7261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0033  -13.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869  -12.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3924  -12.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1070  -12.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1059  -13.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3900  -13.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8122  -12.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5580  -12.5831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1063  -11.9772    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6994  -11.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8997  -11.4365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3924  -11.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8124  -13.8883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0335  -10.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361  -11.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856  -11.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5348  -10.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350  -10.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864  -10.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401  -11.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826   -9.2909    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  2  1  0
  3  4  2  0
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  6  5  2  0
  6  1  1  0
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  9  8  2  0
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  3 10  1  0
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 12 11  1  0
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  2 13  1  0
 11 14  1  0
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 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:

   

   ALA4483550

   ---

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: 395.37

Molecular Weight (Monoisotopic): 395.0264

AlogP: 4.73

#Rotatable Bonds: 2

Polar Surface Area: 86.45

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 4.82

Aromatic Rings: 5

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -0.57

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