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Record Information
Version4.0
Creation Date2013-07-22 19:49:44 UTC
Update Date2017-10-23 19:15:53 UTC
HMDB IDHMDB0061129
Secondary Accession Numbers
  • HMDB61129
Metabolite Identification
Common Name6-Methyl-griseofulvin
Description6-Methyl-griseofulvin is a metabolite of griseofulvin. Griseofulvin (marketed under the proprietary name Grifulvin V by Orthoneutrogena Labs, according to FDA orange book) is an antifungal drug that is administered orally. It is used both in animals and in humans, to treat fungal infections of the skin (commonly known as ringworm) and nails. It is produced by culture of some strains of the mold Penicillium griseofulvum, from which it was isolated in 1939. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H17ClO5
Average Molecular Weight336.767
Monoisotopic Molecular Weight336.076451361
IUPAC Name(2S,6'R)-7-chloro-2',4-dimethoxy-6,6'-dimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
Traditional Name(2S,6'R)-7-chloro-2',4-dimethoxy-6,6'-dimethylspiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(C)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC
InChI Identifier
InChI=1S/C17H17ClO5/c1-8-5-11(21-3)13-15(14(8)18)23-17(16(13)20)9(2)6-10(19)7-12(17)22-4/h5,7,9H,6H2,1-4H3/t9-,17+/m1/s1
InChI KeyQNPINWFXONNRKM-XLFHBGCDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzofurans
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Coumaran
  • Benzofuran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Cyclohexenone
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Vinylogous ester
  • Ketone
  • Cyclic ketone
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP2.55ALOGPS
logP2.84ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)17.69ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity86.42 m³·mol⁻¹ChemAxon
Polarizability33.38 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00aj-9114000000-bf0baf8b7848bbcb6c72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0309000000-006b63517dc08a1bb663View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kk-4904000000-9f6ee5360372c4738e5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06e9-3900000000-cf64f017d2e2ee4c8c31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-d09a1215bdc61824ce7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029000000-e1a883edad5f62526719View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9670000000-debd5bc9d6c57ffc0aa4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00765
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available