Grifolin (CHEM024460)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:42:53 UTC
Update Date2016-11-09 01:17:53 UTC
Accession NumberCHEM024460
Identification
Common NameGrifolin
ClassSmall Molecule
DescriptionGrifolin is found in mushrooms. Grifolin is isolated from the edible maitake mushroom (Grifola confluens
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3,8,12-Trimethyl-5,7,11-tridecatriene-3,4-diolMeSH
2-Farnesyl-5-methylresorcinolHMDB
5-Methyl-2-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol, 9ciHMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenolHMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenoxideHMDB
Ammonium, hexadecyltrimethyl-, pentachlorophenoxide (8ci)HMDB
e,e,5-Methyl-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediolHMDB
Hexadecyltrimethylammonium pentachlorophenolHMDB
Hexadecyltrimethylammonium pentachlorophenoxide (6ci,7ci)HMDB
Trimethylcetylammonium pentachlorophenateHMDB
GrifolinMeSH
Chemical FormulaC22H32O2
Average Molecular Mass328.488 g/mol
Monoisotopic Mass328.240 g/mol
CAS Registry Number6903-07-7
IUPAC Name5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol
Traditional Name5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene-1,3-diol
SMILESCC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O
InChI IdentifierInChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+
InChI KeyPZHNKNRPGLTZPO-VZRGJMDUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Resorcinol
  • M-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP6.69ALOGPS
logP6.93ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.91 m³·mol⁻¹ChemAxon
Polarizability40.44 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvj-3942000000-2bee1b20893cdc0d8a08Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4r-5506900000-80b9eb2eee557fe0c2f2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0549000000-43065ed9c2de04617841Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tr-1920000000-743b2ca32fcdb3c3bddcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-8900000000-5748a3a70df6e1f653ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-5761757dcee8ed7bbe30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0219000000-45ec07490ddb6554caa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-2932000000-af2aa9395deb57466368Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0109000000-55ca267c88fd3e767cacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0927000000-3b2c61b285bed01d3901Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00vm-1930000000-78c42ae7f2bffb8b11dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1935000000-3e05ade6d1af2b95f7e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-2900000000-798a02baa2ee48984578Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-3900000000-367bc194ef877b30082bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030446
FooDB IDFDB002311
Phenol Explorer IDNot Available
KNApSAcK IDC00023937
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGrifolin
Chemspider ID4522608
ChEBI ID544843
PubChem Compound ID5372312
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Luo XJ, Li LL, Deng QP, Yu XF, Yang LF, Luo FJ, Xiao LB, Chen XY, Ye M, Liu JK, Cao Y: Grifolin, a potent antitumour natural product upregulates death-associated protein kinase 1 DAPK1 via p53 in nasopharyngeal carcinoma cells. Eur J Cancer. 2011 Jan;47(2):316-25. doi: 10.1016/j.ejca.2010.09.021. Epub 2010 Oct 11.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM