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

ID: ALA4099965

PubChem CID: 137658598

Max Phase: Preclinical

Molecular Formula: C17H17FO7

Molecular Weight: 352.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H17FO7/c1-7-14(20)8(19)5-11(23-3)17(7)16(21)12-9(25-17)6-10(22-2)13(18)15(12)24-4/h5-7,14,20H,1-4H3/t7-,14-,17+/m1/s1

Standard InChI Key:  MNOZPUZRKUFYAG-DKNUKLLMSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.1862  -10.9611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6664  -10.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1862   -9.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4090   -9.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4090  -10.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6999   -9.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9949   -9.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9949  -10.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6999  -11.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0749   -9.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8921   -9.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3007  -10.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8921  -11.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0749  -11.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4368   -8.8615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1179  -10.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6664  -11.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2858  -11.1151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5768  -10.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6999   -8.6635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9949   -8.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9342   -8.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5567   -8.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3007  -11.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2858   -9.4807    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
 13 24  1  6
  7 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099965

   ---

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: 352.31

Molecular Weight (Monoisotopic): 352.0958

AlogP: 1.27

#Rotatable Bonds: 3

Polar Surface Area: 91.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.03

CX Basic pKa: ┄

CX LogP: 0.88

CX LogD: 0.88

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.88

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