(2S,6'R)-6-Hydroxy-2',4-dimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione; 6-O-desmethyl-7-dechlorogriseofulvin

ID: ALA4064252

PubChem CID: 137636924

Max Phase: Preclinical

Molecular Formula: C16H16O6

Molecular Weight: 304.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H16O6/c1-8-4-9(17)7-13(21-3)16(8)15(19)14-11(20-2)5-10(18)6-12(14)22-16/h5-8,18H,4H2,1-3H3/t8-,16+/m1/s1

Standard InChI Key:  XDFGVAVOCNAUJB-BCTVWOGZSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   11.7544   -7.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2205   -8.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7189   -8.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9292   -8.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9557   -7.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2495   -7.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5307   -7.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5003   -8.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2055   -9.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7790   -8.9631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2795   -6.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9918   -6.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6148   -8.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4430   -8.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8637   -8.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4598   -7.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6411   -7.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2433   -6.8122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6644   -6.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6865   -8.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1922   -9.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7476   -6.7254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  5  1  0
  5  6  2  0
  7  6  1  0
  8  7  2  0
  9  8  1  0
  4  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
  2 13  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
 17 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 15 20  2  0
 13 21  1  1
  1 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4064252

   ---

Molecule Features

Natural Product: Yes

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: 304.30

Molecular Weight (Monoisotopic): 304.0947

AlogP: 1.85

#Rotatable Bonds: 2

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.71

CX Basic pKa: ┄

CX LogP: 1.42

CX LogD: 1.25

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.90

Np Likeness Score: 2.48

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