(-)9-(3-Bromo-4-fluoro-phenyl)-1,1-dioxo-1,3,4,5,6,9-hexahydro-2H-1lambda*6*-furo[3,4-b]thiopyrano[2,3-e]pyridin-8-one

ID: ALA3392139

PubChem CID: 10201843

Max Phase: Preclinical

Molecular Formula: C16H13BrFNO4S

Molecular Weight: 414.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1OCC2=C1C(c1ccc(F)c(Br)c1)C1=C(CCCS1(=O)=O)N2

Standard InChI:  InChI=1S/C16H13BrFNO4S/c17-9-6-8(3-4-10(9)18)13-14-12(7-23-16(14)20)19-11-2-1-5-24(21,22)15(11)13/h3-4,6,13,19H,1-2,5,7H2

Standard InChI Key:  LLOBVWCCGRYZQL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    2.7655    0.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5142    0.7225    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516    0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302    0.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -0.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6208   -0.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8384   -0.6285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430    1.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884    1.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    0.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531    2.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3921   -0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886    1.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954    0.9987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031    3.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5884    3.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0654    2.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5398    1.9293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1190    0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    2.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126   -0.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1782    3.7093    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    4.2495    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9669   -0.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  1  1  0
  5  7  1  0
  6  1  2  0
  7  6  1  0
  8  3  1  0
  9  4  1  0
 10  8  1  0
 11  9  2  0
 12  5  1  0
 13  2  2  0
 14  2  2  0
 15 11  1  0
 16 20  1  0
 17  9  1  0
 18  8  2  0
 19  2  1  0
 20 17  2  0
 21  6  1  0
 22 15  1  0
 23 16  1  0
 24 21  1  0
 19 24  1  0
  3  5  2  0
 12 10  1  0
 15 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3392139

   8-(3-Bromo-4-fluorophenyl)-10,10-dioxo-5-oxa-10lambda6-thia-2-azatricyclo[7.4.0.03,7]trideca-1(9),3(7)-dien-6-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: 414.25

Molecular Weight (Monoisotopic): 412.9733

AlogP: 2.51

#Rotatable Bonds: 1

Polar Surface Area: 72.47

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.29

CX Basic pKa: ┄

CX LogP: 1.04

CX LogD: 1.04

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.72

References

1. Carroll WA, Agrios KA, Altenbach RJ, Buckner SA, Chen Y, Coghlan MJ, Daza AV, Drizin I, Gopalakrishnan M, Henry RF, Kort ME, Kym PR, Milicic I, Smith JC, Tang R, Turner SC, Whiteaker KL, Zhang H, Sullivan JP..  (2004)  Synthesis and structure-activity relationships of a novel series of tricyclic dihydropyridine-based KATP openers that potently inhibit bladder contractions in vitro.,  47  (12): [PMID:15163197] [10.1021/jm030357o]

2. Carroll WA, Agrios KA, Altenbach RJ, Buckner SA, Chen Y, Coghlan MJ, Daza AV, Drizin I, Gopalakrishnan M, Henry RF, Kort ME, Kym PR, Milicic I, Smith JC, Tang R, Turner SC, Whiteaker KL, Zhang H, Sullivan JP..  (2004)  Synthesis and structure-activity relationships of a novel series of tricyclic dihydropyridine-based KATP openers that potently inhibit bladder contractions in vitro.,  47  (12): [PMID:15163197] [10.1021/jm030357o]

Source

Source(1):

• Scientific Literature