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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:06 UTC
Update Date2022-03-07 02:52:42 UTC
HMDB IDHMDB0030798
Secondary Accession Numbers
  • HMDB30798
Metabolite Identification
Common NameMyricanone
DescriptionMyricanone 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. Myricanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Myricanone.
Structure
Data?1563862039
Synonyms
ValueSource
MyricanoneMeSH
Chemical FormulaC21H24O5
Average Molecular Weight356.4123
Monoisotopic Molecular Weight356.162373878
IUPAC Name3,15-dihydroxy-16,17-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
Traditional Name3,15-dihydroxy-16,17-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
CAS Registry Number32492-74-3
SMILES
COC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C1
InChI Identifier
InChI=1S/C21H24O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,23-24H,3-7,9H2,1-2H3
InChI KeyZTSNTUQTNQSIDC-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 Parents
Substituents
  • Meta,meta-bridged biphenyl
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Cyclic ketone
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point194 - 196 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.95ALOGPS
logP4.3ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.98ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity100.01 m³·mol⁻¹ChemAxon
Polarizability37.67 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
DarkChem[M+H]+185.27631661259
DarkChem[M-H]-184.59531661259
DeepCCS[M+H]+194.22130932474
DeepCCS[M-H]-191.86330932474
DeepCCS[M-2H]-226.15530932474
DeepCCS[M+Na]+201.38230932474
AllCCS[M+H]+185.732859911
AllCCS[M+H-H2O]+182.732859911
AllCCS[M+NH4]+188.432859911
AllCCS[M+Na]+189.132859911
AllCCS[M-H]-188.432859911
AllCCS[M+Na-2H]-188.532859911
AllCCS[M+HCOO]-188.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MyricanoneCOC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C14287.2Standard polar33892256
MyricanoneCOC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C13021.3Standard non polar33892256
MyricanoneCOC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C13103.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Myricanone,1TMS,isomer #1COC1=C2C=C(CCCCC(=O)CCC3=CC2=C(O)C=C3)C(O[Si](C)(C)C)=C1OC3191.6Semi standard non polar33892256
Myricanone,1TMS,isomer #2COC1=C2C=C(CCCCC(=O)CCC3=CC2=C(O[Si](C)(C)C)C=C3)C(O)=C1OC3165.6Semi standard non polar33892256
Myricanone,1TMS,isomer #3COC1=C2C=C(CCCC=C(O[Si](C)(C)C)CCC3=CC2=C(O)C=C3)C(O)=C1OC3153.5Semi standard non polar33892256
Myricanone,1TMS,isomer #4COC1=C2C=C(CCCCC(O[Si](C)(C)C)=CCC3=CC2=C(O)C=C3)C(O)=C1OC3159.6Semi standard non polar33892256
Myricanone,2TMS,isomer #1COC1=C2C=C(CCCCC(=O)CCC3=CC2=C(O[Si](C)(C)C)C=C3)C(O[Si](C)(C)C)=C1OC3123.2Semi standard non polar33892256
Myricanone,2TMS,isomer #2COC1=C2C=C(CCCCC(O[Si](C)(C)C)=CCC3=CC2=C(O)C=C3)C(O[Si](C)(C)C)=C1OC3132.0Semi standard non polar33892256
Myricanone,2TMS,isomer #3COC1=C2C=C(CCCC=C(O[Si](C)(C)C)CCC3=CC2=C(O)C=C3)C(O[Si](C)(C)C)=C1OC3122.6Semi standard non polar33892256
Myricanone,2TMS,isomer #4COC1=C2C=C(CCCCC(O[Si](C)(C)C)=CCC3=CC2=C(O[Si](C)(C)C)C=C3)C(O)=C1OC3105.9Semi standard non polar33892256
Myricanone,2TMS,isomer #5COC1=C2C=C(CCCC=C(O[Si](C)(C)C)CCC3=CC2=C(O[Si](C)(C)C)C=C3)C(O)=C1OC3085.6Semi standard non polar33892256
Myricanone,3TMS,isomer #1COC1=C2C=C(CCCCC(O[Si](C)(C)C)=CCC3=CC2=C(O[Si](C)(C)C)C=C3)C(O[Si](C)(C)C)=C1OC3104.6Semi standard non polar33892256
Myricanone,3TMS,isomer #1COC1=C2C=C(CCCCC(O[Si](C)(C)C)=CCC3=CC2=C(O[Si](C)(C)C)C=C3)C(O[Si](C)(C)C)=C1OC3012.9Standard non polar33892256
Myricanone,3TMS,isomer #2COC1=C2C=C(CCCC=C(O[Si](C)(C)C)CCC3=CC2=C(O[Si](C)(C)C)C=C3)C(O[Si](C)(C)C)=C1OC3079.1Semi standard non polar33892256
Myricanone,3TMS,isomer #2COC1=C2C=C(CCCC=C(O[Si](C)(C)C)CCC3=CC2=C(O[Si](C)(C)C)C=C3)C(O[Si](C)(C)C)=C1OC3046.8Standard non polar33892256
Myricanone,1TBDMS,isomer #1COC1=C2C=C(CCCCC(=O)CCC3=CC2=C(O)C=C3)C(O[Si](C)(C)C(C)(C)C)=C1OC3405.3Semi standard non polar33892256
Myricanone,1TBDMS,isomer #2COC1=C2C=C(CCCCC(=O)CCC3=CC2=C(O[Si](C)(C)C(C)(C)C)C=C3)C(O)=C1OC3387.7Semi standard non polar33892256
Myricanone,1TBDMS,isomer #3COC1=C2C=C(CCCC=C(O[Si](C)(C)C(C)(C)C)CCC3=CC2=C(O)C=C3)C(O)=C1OC3402.0Semi standard non polar33892256
Myricanone,1TBDMS,isomer #4COC1=C2C=C(CCCCC(O[Si](C)(C)C(C)(C)C)=CCC3=CC2=C(O)C=C3)C(O)=C1OC3403.7Semi standard non polar33892256
Myricanone,2TBDMS,isomer #1COC1=C2C=C(CCCCC(=O)CCC3=CC2=C(O[Si](C)(C)C(C)(C)C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C1OC3538.4Semi standard non polar33892256
Myricanone,2TBDMS,isomer #2COC1=C2C=C(CCCCC(O[Si](C)(C)C(C)(C)C)=CCC3=CC2=C(O)C=C3)C(O[Si](C)(C)C(C)(C)C)=C1OC3557.2Semi standard non polar33892256
Myricanone,2TBDMS,isomer #3COC1=C2C=C(CCCC=C(O[Si](C)(C)C(C)(C)C)CCC3=CC2=C(O)C=C3)C(O[Si](C)(C)C(C)(C)C)=C1OC3546.7Semi standard non polar33892256
Myricanone,2TBDMS,isomer #4COC1=C2C=C(CCCCC(O[Si](C)(C)C(C)(C)C)=CCC3=CC2=C(O[Si](C)(C)C(C)(C)C)C=C3)C(O)=C1OC3531.0Semi standard non polar33892256
Myricanone,2TBDMS,isomer #5COC1=C2C=C(CCCC=C(O[Si](C)(C)C(C)(C)C)CCC3=CC2=C(O[Si](C)(C)C(C)(C)C)C=C3)C(O)=C1OC3502.2Semi standard non polar33892256
Myricanone,3TBDMS,isomer #1COC1=C2C=C(CCCCC(O[Si](C)(C)C(C)(C)C)=CCC3=CC2=C(O[Si](C)(C)C(C)(C)C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C1OC3709.6Semi standard non polar33892256
Myricanone,3TBDMS,isomer #1COC1=C2C=C(CCCCC(O[Si](C)(C)C(C)(C)C)=CCC3=CC2=C(O[Si](C)(C)C(C)(C)C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C1OC3512.4Standard non polar33892256
Myricanone,3TBDMS,isomer #2COC1=C2C=C(CCCC=C(O[Si](C)(C)C(C)(C)C)CCC3=CC2=C(O[Si](C)(C)C(C)(C)C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C1OC3668.7Semi standard non polar33892256
Myricanone,3TBDMS,isomer #2COC1=C2C=C(CCCC=C(O[Si](C)(C)C(C)(C)C)CCC3=CC2=C(O[Si](C)(C)C(C)(C)C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C1OC3562.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Myricanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0019000000-140014aeda9269180bd02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanone GC-MS (2 TMS) - 70eV, Positivesplash10-007a-2003900000-d0c3e71b42796ce2c0232017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myricanone 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 - Myricanone 10V, Positive-QTOFsplash10-0a4i-0009000000-e5b899dfce8a2bc512192015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 20V, Positive-QTOFsplash10-0a4i-2019000000-25228067625de7e9f4292015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 40V, Positive-QTOFsplash10-0aou-9157000000-20a1259ffe7b85de4b7e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 10V, Negative-QTOFsplash10-0a4i-0009000000-3f9bff3a100296c0e2072015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 20V, Negative-QTOFsplash10-0a4i-0009000000-cf8243097f25e6cb44312015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 40V, Negative-QTOFsplash10-00ko-4096000000-1db7e65c44f1cd718ef52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 10V, Negative-QTOFsplash10-0a4i-0009000000-a9228afe3c44e821e4832021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 20V, Negative-QTOFsplash10-0a4i-0009000000-4564b88af9a595f929332021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 40V, Negative-QTOFsplash10-000i-0094000000-9f0b22d5dc06c99350732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 10V, Positive-QTOFsplash10-052r-0009000000-041d36ff41c95d451dc62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 20V, Positive-QTOFsplash10-052r-0009000000-ca15c4bec511a3dc90902021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myricanone 40V, Positive-QTOFsplash10-00dr-0097000000-952d857b70cb211b8d622021-09-24Wishart 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 IDFDB002739
KNApSAcK IDC00033235
Chemspider ID142062
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMyricanone
METLIN IDNot Available
PubChem Compound71438979
PDB IDNot Available
ChEBI ID141540
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:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Myricanone → 3,4,5-trihydroxy-6-({15-hydroxy-16,17-dimethoxy-9-oxotricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-3-yl}oxy)oxane-2-carboxylic aciddetails
Myricanone → 3,4,5-trihydroxy-6-({17-hydroxy-3,4-dimethoxy-11-oxotricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-5-yl}oxy)oxane-2-carboxylic aciddetails