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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:50 UTC
Update Date2022-03-07 02:52:33 UTC
HMDB IDHMDB0030446
Secondary Accession Numbers
  • HMDB30446
Metabolite Identification
Common NameGrifolin
DescriptionGrifolin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Grifolin.
Structure
Data?1563861986
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 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
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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point43 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0017 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.62231661259
DarkChem[M-H]-182.18631661259
DeepCCS[M+H]+184.87130932474
DeepCCS[M-H]-182.51330932474
DeepCCS[M-2H]-216.25630932474
DeepCCS[M+Na]+191.60930932474
AllCCS[M+H]+188.032859911
AllCCS[M+H-H2O]+185.032859911
AllCCS[M+NH4]+190.832859911
AllCCS[M+Na]+191.632859911
AllCCS[M-H]-183.432859911
AllCCS[M+Na-2H]-183.932859911
AllCCS[M+HCOO]-184.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GrifolinCC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O3669.9Standard polar33892256
GrifolinCC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O2519.8Standard non polar33892256
GrifolinCC(C)=CCC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)C=C1O2686.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Grifolin,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1=C(O)C=C(C)C=C1O[Si](C)(C)C2602.2Semi standard non polar33892256
Grifolin,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1=C(O[Si](C)(C)C)C=C(C)C=C1O[Si](C)(C)C2579.3Semi standard non polar33892256
Grifolin,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1=C(O)C=C(C)C=C1O[Si](C)(C)C(C)(C)C2851.4Semi standard non polar33892256
Grifolin,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC1=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C1O[Si](C)(C)C(C)(C)C3033.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Grifolin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvj-3942000000-2bee1b20893cdc0d8a082017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Grifolin GC-MS (2 TMS) - 70eV, Positivesplash10-0a4r-5506900000-80b9eb2eee557fe0c2f22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Grifolin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Grifolin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 10V, Positive-QTOFsplash10-004i-0549000000-43065ed9c2de046178412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 20V, Positive-QTOFsplash10-05tr-1920000000-743b2ca32fcdb3c3bddc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 40V, Positive-QTOFsplash10-0gbi-8900000000-5748a3a70df6e1f653eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 10V, Negative-QTOFsplash10-004i-0009000000-5761757dcee8ed7bbe302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 20V, Negative-QTOFsplash10-004i-0219000000-45ec07490ddb6554caa72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 40V, Negative-QTOFsplash10-0229-2932000000-af2aa9395deb574663682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 10V, Negative-QTOFsplash10-004i-0109000000-55ca267c88fd3e767cac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 20V, Negative-QTOFsplash10-004r-0927000000-3b2c61b285bed01d39012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 40V, Negative-QTOFsplash10-00vm-1930000000-78c42ae7f2bffb8b11db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 10V, Positive-QTOFsplash10-004i-1935000000-3e05ade6d1af2b95f7e02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 20V, Positive-QTOFsplash10-052r-2900000000-798a02baa2ee489845782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Grifolin 40V, Positive-QTOFsplash10-0a4r-3900000000-367bc194ef877b30082b2021-09-23Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1820021
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.