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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:40:46 UTC
Update Date2022-03-07 02:54:57 UTC
HMDB IDHMDB0036526
Secondary Accession Numbers
  • HMDB36526
Metabolite Identification
Common NameMyricanol 5-(6-galloylglucoside)
DescriptionMyricanol 5-(6-galloylglucoside) belongs to the class of organic compounds known as meta,meta-bridged biphenyls. These are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position. Myricanol 5-(6-galloylglucoside) is a constituent of Myrica rubra (Chinese bayberry). Myricanol 5-(6-galloylglucoside) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862885
Synonyms
ValueSource
[6-({11,17-dihydroxy-3,4-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-5-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC34H40O14
Average Molecular Weight672.673
Monoisotopic Molecular Weight672.241805988
IUPAC Name[6-({11,17-dihydroxy-3,4-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-5-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Traditional Name[6-({11,17-dihydroxy-3,4-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-5-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
CAS Registry Number113204-18-5
SMILES
COC1=C(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C1
InChI Identifier
InChI=1S/C34H40O14/c1-44-31-21-12-17(5-3-4-6-19(35)9-7-16-8-10-22(36)20(21)11-16)30(32(31)45-2)48-34-29(42)28(41)27(40)25(47-34)15-46-33(43)18-13-23(37)26(39)24(38)14-18/h8,10-14,19,25,27-29,34-42H,3-7,9,15H2,1-2H3
InChI KeyPXTKHOHAJHGCKB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as meta,meta-bridged biphenyls. These are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassCyclic diarylheptanoids
Direct ParentMeta,meta-bridged biphenyls
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point267 - 269 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.72ALOGPS
logP3.41ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity168.95 m³·mol⁻¹ChemAxon
Polarizability67.84 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+247.45531661259
DarkChem[M-H]-242.37631661259
DeepCCS[M+H]+254.40930932474
DeepCCS[M-H]-252.58430932474
DeepCCS[M-2H]-285.82730932474
DeepCCS[M+Na]+260.01530932474
AllCCS[M+H]+245.832859911
AllCCS[M+H-H2O]+245.132859911
AllCCS[M+NH4]+246.332859911
AllCCS[M+Na]+246.532859911
AllCCS[M-H]-232.832859911
AllCCS[M+Na-2H]-235.932859911
AllCCS[M+HCOO]-239.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Myricanol 5-(6-galloylglucoside)COC1=C(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C15574.4Standard polar33892256
Myricanol 5-(6-galloylglucoside)COC1=C(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C15331.6Standard non polar33892256
Myricanol 5-(6-galloylglucoside)COC1=C(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C15815.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-5942416000-0f5c88ea3cb18de625862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanol 5-(6-galloylglucoside) GC-MS (TMS_2_17) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 10V, Positive-QTOFsplash10-0a4i-0209115000-c2869ee3b4616562a4a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 20V, Positive-QTOFsplash10-052f-0109000000-e2642df9dae01d072e412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 40V, Positive-QTOFsplash10-0zg3-0519000000-351bfdcb47bc19a343202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 10V, Negative-QTOFsplash10-01b9-0916006000-38a87adfef1800d669b62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 20V, Negative-QTOFsplash10-066r-0907001000-d0715cd66192b613de652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 40V, Negative-QTOFsplash10-066u-1729000000-5e2180bd84399afed8f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 10V, Negative-QTOFsplash10-00di-0101019000-bcf101677a891061514d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 20V, Negative-QTOFsplash10-0udr-0903224000-2d60b28d16daaf5a70c12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 40V, Negative-QTOFsplash10-00mo-0309000000-e6dee83140da154e985f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 10V, Positive-QTOFsplash10-052f-0209002000-bfaf6a84a83b17306ab22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 20V, Positive-QTOFsplash10-0zg0-0914207000-36cb52fbba2d1b6f190b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanol 5-(6-galloylglucoside) 40V, Positive-QTOFsplash10-0umi-0905000000-a5610cbcce33683b4e802021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB015426
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14031379
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Myricanol 5-(6-galloylglucoside) → Myricanol 5-glucosidedetails