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

ID: ALA4559221

PubChem CID: 155557971

Max Phase: Preclinical

Molecular Formula: C18H13NO5S

Molecular Weight: 355.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(-c2nsc(=O)o2)c(=O)oc2cc3occ(C4CCC4)c3cc12

Standard InChI:  InChI=1S/C18H13NO5S/c1-8-10-5-11-12(9-3-2-4-9)7-22-13(11)6-14(10)23-17(20)15(8)16-19-25-18(21)24-16/h5-7,9H,2-4H2,1H3

Standard InChI Key:  GDXRHRGDWMOKAF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.3720  -21.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0776  -21.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0788  -20.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3702  -20.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6652  -20.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6639  -21.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8827  -21.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4010  -20.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8846  -20.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7901  -20.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5047  -20.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5036  -21.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7877  -21.8072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2099  -20.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9557  -20.5033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5040  -19.8973    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0971  -19.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2974  -19.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7901  -19.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2101  -21.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4312  -18.4428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6334  -19.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0055  -18.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2780  -18.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9059  -19.1706    0.0000 C   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  1  0
 23 24  1  0
 24 25  1  0
 25 22  1  0
  9 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559221

   ---

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: 355.37

Molecular Weight (Monoisotopic): 355.0514

AlogP: 4.19

#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: 4.26

CX LogD: 4.26

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -0.06

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