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

ID: ALA4104629

PubChem CID: 137658162

Max Phase: Preclinical

Molecular Formula: C17H17ClO7

Molecular Weight: 368.77

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H17ClO7/c1-7-14(20)8(19)5-11(24-4)17(7)16(21)12-9(22-2)6-10(23-3)13(18)15(12)25-17/h5-7,14,20H,1-4H3/t7-,14-,17+/m1/s1

Standard InChI Key:  SJUXBYNINSBOOT-DKNUKLLMSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.2950   -9.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7612  -10.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2596  -10.9768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4698  -10.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4962   -9.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7901   -9.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0713   -9.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0408  -10.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7461  -11.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7161  -11.9178    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.3195  -11.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6205  -10.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8200   -8.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5324   -8.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1555  -11.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9837  -11.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4044  -10.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0005   -9.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1817   -9.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7839   -8.8937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2051   -8.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2273  -10.3522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7329  -11.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2882   -8.8070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3839  -11.7709    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
  9 10  1  0
  8 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  1  0
  2 15  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 19 18  2  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 17 22  2  0
 15 23  1  1
  1 24  2  0
 16 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4104629

   ---

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: 368.77

Molecular Weight (Monoisotopic): 368.0663

AlogP: 1.78

#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: 1.34

CX LogD: 1.34

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: 1.94

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