(2S,6'R)-5-Fluoro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione; 5-Fluoro-7-dechlorogriseofulvin

ID: ALA4074161

PubChem CID: 137641228

Max Phase: Preclinical

Molecular Formula: C17H17FO6

Molecular Weight: 336.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=CC(=O)C[C@@H](C)[C@]12Oc1cc(OC)c(F)c(OC)c1C2=O

Standard InChI:  InChI=1S/C17H17FO6/c1-8-5-9(19)6-12(22-3)17(8)16(20)13-10(24-17)7-11(21-2)14(18)15(13)23-4/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

Standard InChI Key:  SZGBPAXKMROYML-RBHXEPJQSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   11.7219   -9.7591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2020   -9.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7219   -8.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9447   -8.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9447   -9.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2356   -8.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5306   -8.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5306   -9.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2356   -9.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6106   -8.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4278   -8.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8364   -9.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4278   -9.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6106   -9.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9766   -7.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6536   -9.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2020  -10.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8215   -9.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1124   -9.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2356   -7.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5306   -7.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4699   -7.5842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0924   -7.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8215   -8.2786    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  5  9  2  0
  4  6  2  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  2 10  1  0
  2 14  1  0
  3 15  2  0
 12 16  2  0
 14 17  1  1
 18 19  1  0
  8 18  1  0
 20 21  1  0
  6 20  1  0
 22 23  1  0
 10 22  1  0
  7 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4074161

   ---

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: 336.31

Molecular Weight (Monoisotopic): 336.1009

AlogP: 2.30

#Rotatable Bonds: 3

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.71

CX LogD: 1.71

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: 1.75

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