You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:50 UTC
Update Date2019-01-11 19:40:22 UTC
HMDB IDHMDB0030446
Secondary Accession Numbers
  • HMDB30446
Metabolite Identification
Common NameGrifolin
DescriptionGrifolin is found in mushrooms. Grifolin is isolated from the edible maitake mushroom (Grifola confluens
Structure
Data?1547235622
Synonyms
ValueSource
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
Chemical FormulaC22H32O2
Average Molecular Weight328.4883
Monoisotopic Molecular Weight328.240230268
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
CAS Registry Number6903-07-7
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O
InChI Identifier
InChI=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
DescriptionThis compound 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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point43 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvj-3942000000-2bee1b20893cdc0d8a08JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4r-5506900000-80b9eb2eee557fe0c2f2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0549000000-43065ed9c2de04617841JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tr-1920000000-743b2ca32fcdb3c3bddcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-8900000000-5748a3a70df6e1f653ebJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-5761757dcee8ed7bbe30JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0219000000-45ec07490ddb6554caa7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-2932000000-af2aa9395deb57466368JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002311
KNApSAcK IDC00023937
Chemspider ID4522608
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGrifolin
METLIN IDNot Available
PubChem Compound5372312
PDB IDNot Available
ChEBI ID544843
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:20943371 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.