trans-8-(3-bromo-4-fluorophenyl)-5-methyl-1,1-dioxo-1,2,3,4,5,8-hexahydro-6-oxa-1lamda6-thia-4-aza-s-indacen-7-one

ID: ALA3138575

PubChem CID: 44417597

Max Phase: Preclinical

Molecular Formula: C16H13BrFNO4S

Molecular Weight: 414.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1OC(=O)C2=C1NC1=C([C@H]2c2ccc(F)c(Br)c2)S(=O)(=O)CC1

Standard InChI:  InChI=1S/C16H13BrFNO4S/c1-7-14-13(16(20)23-7)12(8-2-3-10(18)9(17)6-8)15-11(19-14)4-5-24(15,21)22/h2-3,6-7,12,19H,4-5H2,1H3/t7-,12+/m1/s1

Standard InChI Key:  WFRDHMRQQHNJFI-KRTXAFLBSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  1  0  0  0  0  0999 V2000
    0.5739    3.3591    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9517   -0.7732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691    0.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537    0.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447   -0.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4525   -0.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0282    0.0696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4671    0.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799    1.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691    2.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790    2.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9990    3.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7105    2.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6971    2.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0104    4.1658    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892   -1.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6751    0.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4630    0.7037    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9415    0.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4493   -0.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750    1.4326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584    0.9217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 12 13  1  0
  3 19  1  0
 13 14  2  0
 14  9  1  0
  3  9  1  6
  5  6  1  0
  8 15  2  0
  6  7  1  0
 12 16  1  0
 11  1  1  0
  7  8  1  0
  6 17  1  1
  8  4  1  0
 18 19  2  0
  4  5  2  0
 18  2  1  0
  9 10  2  0
  2  5  1  0
 10 11  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 20 23  2  0
 11 12  2  0
 20 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3138575

   (4R,8S)-8-(3-bromo-4-fluorophenyl)-4-methyl-10,10-dioxo-5-oxa-10lambda6-thia-2-azatricyclo[7.3.0.03,7]dodeca-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: 2.50

#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: 13.40

CX Basic pKa: ┄

CX LogP: 0.94

CX LogD: 0.94

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.34

References

1. Altenbach RJ, Brune ME, Buckner SA, Coghlan MJ, Daza AV, Fabiyi A, Gopalakrishnan M, Henry RF, Khilevich A, Kort ME, Milicic I, Scott VE, Smith JC, Whiteaker KL, Carroll WA..  (2006)  Effects of substitution on 9-(3-bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2,6-dioxa-4- azacyclopenta[b]naphthalene-1,8-dione, a dihydropyridine ATP-sensitive potassium channel opener.,  49  (23): [PMID:17154517] [10.1021/jm060549u]

Source

Source(1):

• Scientific Literature