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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:07 UTC
Update Date2022-03-07 02:52:42 UTC
HMDB IDHMDB0030799
Secondary Accession Numbers
  • HMDB30799
Metabolite Identification
Common Name5-Deoxymyricanone
Description5-Deoxymyricanone 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. 5-Deoxymyricanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-deoxymyricanone has been detected, but not quantified in, fruits. This could make 5-deoxymyricanone a potential biomarker for the consumption of these foods.
Structure
Data?1563862039
SynonymsNot Available
Chemical FormulaC21H24O4
Average Molecular Weight340.4129
Monoisotopic Molecular Weight340.167459256
IUPAC Name3-hydroxy-16,17-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
Traditional Name3-hydroxy-16,17-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
CAS Registry Number110007-10-8
SMILES
COC1=CC2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C1
InChI Identifier
InChI=1S/C21H24O4/c1-24-20-13-15-5-3-4-6-16(22)9-7-14-8-10-19(23)17(11-14)18(12-15)21(20)25-2/h8,10-13,23H,3-7,9H2,1-2H3
InChI KeyUCIYWYZLILBGOL-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 homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.005 g/LALOGPS
logP4.34ALOGPS
logP4.61ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98.03 m³·mol⁻¹ChemAxon
Polarizability36.82 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]+179.85831661259
DarkChem[M-H]-181.131661259
DeepCCS[M+H]+188.71930932474
DeepCCS[M-H]-186.36130932474
DeepCCS[M-2H]-220.42830932474
DeepCCS[M+Na]+195.65530932474
AllCCS[M+H]+182.832859911
AllCCS[M+H-H2O]+179.732859911
AllCCS[M+NH4]+185.632859911
AllCCS[M+Na]+186.432859911
AllCCS[M-H]-186.332859911
AllCCS[M+Na-2H]-186.332859911
AllCCS[M+HCOO]-186.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-DeoxymyricanoneCOC1=CC2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C13892.5Standard polar33892256
5-DeoxymyricanoneCOC1=CC2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C12895.0Standard non polar33892256
5-DeoxymyricanoneCOC1=CC2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C12920.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Deoxymyricanone,1TMS,isomer #1COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C)CCC(=O)CCCC23007.7Semi standard non polar33892256
5-Deoxymyricanone,1TMS,isomer #2COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O)CCC(O[Si](C)(C)C)=CCCC23016.9Semi standard non polar33892256
5-Deoxymyricanone,1TMS,isomer #3COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O)CC=C(O[Si](C)(C)C)CCCC23014.8Semi standard non polar33892256
5-Deoxymyricanone,2TMS,isomer #1COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C)CCC(O[Si](C)(C)C)=CCCC22956.0Semi standard non polar33892256
5-Deoxymyricanone,2TMS,isomer #1COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C)CCC(O[Si](C)(C)C)=CCCC22898.9Standard non polar33892256
5-Deoxymyricanone,2TMS,isomer #2COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C)CC=C(O[Si](C)(C)C)CCCC22973.9Semi standard non polar33892256
5-Deoxymyricanone,2TMS,isomer #2COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C)CC=C(O[Si](C)(C)C)CCCC22884.9Standard non polar33892256
5-Deoxymyricanone,1TBDMS,isomer #1COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C(C)(C)C)CCC(=O)CCCC23240.6Semi standard non polar33892256
5-Deoxymyricanone,1TBDMS,isomer #2COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O)CCC(O[Si](C)(C)C(C)(C)C)=CCCC23272.7Semi standard non polar33892256
5-Deoxymyricanone,1TBDMS,isomer #3COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O)CC=C(O[Si](C)(C)C(C)(C)C)CCCC23277.9Semi standard non polar33892256
5-Deoxymyricanone,2TBDMS,isomer #1COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C(C)(C)C)CCC(O[Si](C)(C)C(C)(C)C)=CCCC23420.7Semi standard non polar33892256
5-Deoxymyricanone,2TBDMS,isomer #1COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C(C)(C)C)CCC(O[Si](C)(C)C(C)(C)C)=CCCC23288.5Standard non polar33892256
5-Deoxymyricanone,2TBDMS,isomer #2COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C(C)(C)C)CC=C(O[Si](C)(C)C(C)(C)C)CCCC23442.7Semi standard non polar33892256
5-Deoxymyricanone,2TBDMS,isomer #2COC1=CC2=CC(=C1OC)C1=CC(=CC=C1O[Si](C)(C)C(C)(C)C)CC=C(O[Si](C)(C)C(C)(C)C)CCCC23257.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Deoxymyricanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-0079000000-4900091edd2e912c57ec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Deoxymyricanone GC-MS (1 TMS) - 70eV, Positivesplash10-006t-2009000000-898c8c1c10d610cad58a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Deoxymyricanone 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 - 5-Deoxymyricanone 10V, Positive-QTOFsplash10-0006-0009000000-913748d90cf816c0038e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 20V, Positive-QTOFsplash10-006x-2179000000-933170d4386e995b258e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 40V, Positive-QTOFsplash10-0292-2392000000-bb9bf2ec202f226339802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 10V, Negative-QTOFsplash10-000i-0009000000-7ab2f31513526cd86d4c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 20V, Negative-QTOFsplash10-000i-0009000000-43c6f54a933c89a959f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 40V, Negative-QTOFsplash10-0006-6094000000-b85d7be453cd6f2026862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 10V, Negative-QTOFsplash10-000i-0009000000-7b9c90db07ee316cee162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 20V, Negative-QTOFsplash10-000i-0029000000-3ac8c53be5af707737992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 40V, Negative-QTOFsplash10-004i-0091000000-716f6a13b1ead4f8537d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 10V, Positive-QTOFsplash10-00dl-0009000000-b245455e2e6efd9c15fb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 20V, Positive-QTOFsplash10-00dl-0009000000-25c29361084cc324f2ba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Deoxymyricanone 40V, Positive-QTOFsplash10-0a74-0094000000-3a666db3ed043b6906732021-09-23Wishart 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 IDFDB002740
KNApSAcK IDNot Available
Chemspider ID10273166
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21637794
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:
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
5-Deoxymyricanone → 6-({16,17-dimethoxy-9-oxotricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails