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

ID: ALA4084464

PubChem CID: 137647518

Max Phase: Preclinical

Molecular Formula: C17H16ClFO6

Molecular Weight: 370.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=CC(=O)C[C@@H](C)[C@]12Oc1c(Cl)c(OC)c(F)c(OC)c1C2=O

Standard InChI:  InChI=1S/C17H16ClFO6/c1-7-5-8(20)6-9(22-2)17(7)16(21)10-13(25-17)11(18)15(24-4)12(19)14(10)23-3/h6-7H,5H2,1-4H3/t7-,17+/m1/s1

Standard InChI Key:  GIRXJTBLCXBTBM-GJEGPGMTSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.1883  -10.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6684  -10.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1883   -9.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4110   -9.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4110  -10.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7020   -9.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9970   -9.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9970  -10.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7020  -11.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0770   -9.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8942   -9.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3028  -10.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8942  -10.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0770  -10.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4429   -8.7546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1200  -10.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6684  -11.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2879  -11.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5788  -10.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7020   -8.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9970   -8.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9363   -8.6794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5587   -8.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2879   -9.3738    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7020  -11.8254    0.0000 Cl  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
  9 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084464

   ---

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: 370.76

Molecular Weight (Monoisotopic): 370.0619

AlogP: 2.95

#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: 2.31

CX LogD: 2.31

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.81

Np Likeness Score: 1.51

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