(1'S,6'R)-7-chloro-7-fluoro-2',6-dimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4,4'(7H)-trione

ID: ALA4100920

PubChem CID: 137658650

Max Phase: Preclinical

Molecular Formula: C16H14ClFO6

Molecular Weight: 356.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=CC(=O)C2=C(O[C@]3(C2=O)C(OC)=CC(=O)C[C@H]3C)C1(F)Cl

Standard InChI:  InChI=1S/C16H14ClFO6/c1-7-4-8(19)5-10(22-2)15(7)13(21)12-9(20)6-11(23-3)16(17,18)14(12)24-15/h5-7H,4H2,1-3H3/t7-,15+,16?/m1/s1

Standard InChI Key:  USFZVJASQVGAMR-UCZZMTCQSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   10.7102  -10.0085    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.3057   -9.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8967  -10.0059    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.7921   -9.1497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2722   -8.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7921   -7.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0148   -8.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0148   -8.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3057   -7.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6008   -8.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6008   -8.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6808   -7.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4980   -7.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9066   -8.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4980   -9.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6808   -9.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0467   -7.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7238   -8.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2722   -9.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8917   -9.3036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1826   -8.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5401   -6.9748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1625   -6.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3047   -6.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  1
  6  7  1  0
  7  8  2  0
  4  8  1  0
  9 10  1  0
 10 11  2  0
 11  2  1  0
  8  2  1  0
  7  9  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  5 12  1  0
  5 16  1  0
  6 17  2  0
 14 18  2  0
 16 19  1  1
 20 21  1  0
 11 20  1  0
 22 23  1  0
 12 22  1  0
  9 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100920

   ---

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: 356.73

Molecular Weight (Monoisotopic): 356.0463

AlogP: 1.74

#Rotatable Bonds: 2

Polar Surface Area: 78.90

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.48

CX LogD: 1.48

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.55

Np Likeness Score: 1.69

References

1. Paguigan ND, Al-Huniti MH, Raja HA, Czarnecki A, Burdette JE, González-Medina M, Medina-Franco JL, Polyak SJ, Pearce CJ, Croatt MP, Oberlies NH..  (2017)  Chemoselective fluorination and chemoinformatic analysis of griseofulvin: Natural vs fluorinated fungal metabolites.,  25  (20): [PMID:28802670] [10.1016/j.bmc.2017.07.041]

Source

Source(1):

• Scientific Literature