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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014544
Secondary Accession Numbers
  • HMDB14544
Metabolite Identification
Common NameGriseofulvin
DescriptionGriseofulvin is only found in individuals that have used or taken this drug. It is an antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections. [PubChem]Griseofulvin is fungistatic, however the exact mechanism by which it inhibits the growth of dermatophytes is not clear. It is thought to inhibit fungal cell mitosis and nuclear acid synthesis. It also binds to and interferes with the function of spindle and cytoplasmic microtubules by binding to alpha and beta tubulin. It binds to keratin in human cells, then once it reaches the fungal site of action, it binds to fungal microtubes thus altering the fungal process of mitosis.
Structure
Data?1582753191
Synonyms
ValueSource
(+)-GriseofulvinChEBI
AmudaneChEBI
Curling factorChEBI
FulcinChEBI
FulvicinChEBI
GrifulvinChEBI
GrisactinChEBI
GriseofulvinaChEBI
GriseofulvineChEBI
GriseofulvinumChEBI
GrisovinChEBI
GrysioChEBI
LamorylChEBI
LikudenChEBI
PoncylChEBI
SpirofulvinChEBI
SporostatinChEBI
GREKegg
Gris-pegKegg
Grisactin VKegg
Fulvicin u FHMDB
Fulvicin-u-FHMDB
GrisPEGHMDB
Grifulvin VHMDB
Gris pegHMDB
GrisefulineHMDB
V, GrifulvinHMDB
FulvicinUFHMDB
Chemical FormulaC17H17ClO6
Average Molecular Weight352.766
Monoisotopic Molecular Weight352.071365983
IUPAC Name(2S,6'R)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
Traditional Namegriseofulvin
CAS Registry Number126-07-8
SMILES
COC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC
InChI Identifier
InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1
InChI KeyDDUHZTYCFQRHIY-RBHXEPJQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
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 Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.05 g/LNot Available
LogP2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available178.628http://allccs.zhulab.cn/database/detail?ID=AllCCS00000946
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP2.71ALOGPS
logP2.17ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.69ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area71.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.85 m³·mol⁻¹ChemAxon
Polarizability34.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+179.61330932474
DeepCCS[M-H]-177.21730932474
DeepCCS[M-2H]-210.60630932474
DeepCCS[M+Na]+185.75130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GriseofulvinCOC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC3817.7Standard polar33892256
GriseofulvinCOC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC2724.8Standard non polar33892256
GriseofulvinCOC1=CC(OC)=C(Cl)C2=C1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1OC2804.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Griseofulvin,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O2636.3Semi standard non polar33892256
Griseofulvin,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O2563.8Standard non polar33892256
Griseofulvin,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O3345.5Standard polar33892256
Griseofulvin,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O2848.9Semi standard non polar33892256
Griseofulvin,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O2774.9Standard non polar33892256
Griseofulvin,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]12OC1=C(Cl)C(OC)=CC(OC)=C1C2=O3430.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Griseofulvin GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i1-9208000000-bc69e8498dfe1365cbf92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Griseofulvin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin LC-ESI-qTof , Positive-QTOFsplash10-0uxr-0589000000-f8705acff560aebbf0572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin LC-ESI-qTof , Positive-QTOFsplash10-0uxr-0469000000-196c982b619369269fc42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin LC-ESI-qTof , Positive-QTOFsplash10-014i-2960000000-3f14b9f983cc6e713b6a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin Linear Ion Trap , positive-QTOFsplash10-014r-0291000000-6f003312919e202ee0912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin , positive-QTOFsplash10-0uxr-0589000000-f8705acff560aebbf0572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin , positive-QTOFsplash10-0uxr-0469000000-196c982b619369269fc42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin , positive-QTOFsplash10-014i-2960000000-3f14b9f983cc6e713b6a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin 20V, Positive-QTOFsplash10-014i-0491000000-79844b907995e8371fba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin 10V, Positive-QTOFsplash10-0udi-0239000000-7cd02bae189372507c962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Griseofulvin 40V, Positive-QTOFsplash10-014i-0940000000-979db7ec6757627784a32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 10V, Positive-QTOFsplash10-0udi-0019000000-6e8e872e3063f20132162016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 20V, Positive-QTOFsplash10-0gb9-6359000000-b8b346f6cfebc0766adf2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 40V, Positive-QTOFsplash10-052r-7940000000-96dddca714f878c4694c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 10V, Negative-QTOFsplash10-0udi-0009000000-dc216555ed72b685bd2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 20V, Negative-QTOFsplash10-0udr-0019000000-ff656557d1783726dcf22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 40V, Negative-QTOFsplash10-0a4i-6293000000-1552e154d793f60c7d3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 10V, Negative-QTOFsplash10-0udi-0009000000-ccd58a14a68a0a179df42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 20V, Negative-QTOFsplash10-0udi-0239000000-8bf9c021181f8ddf16e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 40V, Negative-QTOFsplash10-0pc0-9351000000-0e6d75fc00dc250731f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 10V, Positive-QTOFsplash10-0udi-0009000000-da99c723afce93a9bc572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 20V, Positive-QTOFsplash10-0udi-0159000000-e96870a8def0c72a7f502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Griseofulvin 40V, Positive-QTOFsplash10-052k-3092000000-e5a2facca3e774b652482021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00400 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00400 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00400
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00002398
Chemspider ID389934
KEGG Compound IDC06686
BioCyc IDCPD-17786
BiGG IDNot Available
Wikipedia LinkGriseofulvin
METLIN IDNot Available
PubChem Compound441140
PDB IDNot Available
ChEBI ID27779
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Yasuda K, Ranade A, Venkataramanan R, Strom S, Chupka J, Ekins S, Schuetz E, Bachmann K: A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97. doi: 10.1124/dmd.108.020701. Epub 2008 May 27. [PubMed:18505790 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Rasmussen BB, Jeppesen U, Gaist D, Brosen K: Griseofulvin and fluvoxamine interactions with the metabolism of theophylline. Ther Drug Monit. 1997 Feb;19(1):56-62. [PubMed:9029748 ]