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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:12:29 UTC
Update Date2022-03-07 02:56:40 UTC
HMDB IDHMDB0040646
Secondary Accession Numbers
  • HMDB40646
Metabolite Identification
Common NameMyrsinone
DescriptionMyrsinone belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6). Based on a literature review a small amount of articles have been published on Myrsinone.
Structure
Data?1563863572
Synonyms
ValueSource
2,3-Dihydroxy-5-undecyl-2,5-cyclohexadiene-1,4-dione, 9ciHMDB
Chemical FormulaC17H26O4
Average Molecular Weight294.3859
Monoisotopic Molecular Weight294.18310932
IUPAC Name2,3-dihydroxy-5-undecylcyclohexa-2,5-diene-1,4-dione
Traditional Name2,3-dihydroxy-5-undecylcyclohexa-2,5-diene-1,4-dione
CAS Registry Number145040-57-9
SMILES
CCCCCCCCCCCC1=CC(=O)C(O)=C(O)C1=O
InChI Identifier
InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-12-14(18)16(20)17(21)15(13)19/h12,20-21H,2-11H2,1H3
InChI KeyJPFXYNDBKFIYLX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentUbiquinones
Alternative Parents
Substituents
  • Ubiquinone skeleton
  • Quinone
  • P-benzoquinone
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Enediol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point120 - 122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.15 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0038 g/LALOGPS
logP4.28ALOGPS
logP4.83ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity85.33 m³·mol⁻¹ChemAxon
Polarizability34.58 ųChemAxon
Number of Rings1ChemAxon
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]+174.21931661259
DarkChem[M-H]-172.78531661259
DeepCCS[M+H]+178.37930932474
DeepCCS[M-H]-175.82930932474
DeepCCS[M-2H]-209.43630932474
DeepCCS[M+Na]+186.06130932474
AllCCS[M+H]+175.732859911
AllCCS[M+H-H2O]+172.532859911
AllCCS[M+NH4]+178.732859911
AllCCS[M+Na]+179.532859911
AllCCS[M-H]-176.632859911
AllCCS[M+Na-2H]-177.132859911
AllCCS[M+HCOO]-177.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MyrsinoneCCCCCCCCCCCC1=CC(=O)C(O)=C(O)C1=O3516.1Standard polar33892256
MyrsinoneCCCCCCCCCCCC1=CC(=O)C(O)=C(O)C1=O2095.8Standard non polar33892256
MyrsinoneCCCCCCCCCCCC1=CC(=O)C(O)=C(O)C1=O2123.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Myrsinone,1TMS,isomer #1CCCCCCCCCCCC1=CC(=O)C(O[Si](C)(C)C)=C(O)C1=O2476.8Semi standard non polar33892256
Myrsinone,1TMS,isomer #2CCCCCCCCCCCC1=CC(=O)C(O)=C(O[Si](C)(C)C)C1=O2488.5Semi standard non polar33892256
Myrsinone,2TMS,isomer #1CCCCCCCCCCCC1=CC(=O)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C1=O2536.8Semi standard non polar33892256
Myrsinone,1TBDMS,isomer #1CCCCCCCCCCCC1=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C(O)C1=O2760.9Semi standard non polar33892256
Myrsinone,1TBDMS,isomer #2CCCCCCCCCCCC1=CC(=O)C(O)=C(O[Si](C)(C)C(C)(C)C)C1=O2765.6Semi standard non polar33892256
Myrsinone,2TBDMS,isomer #1CCCCCCCCCCCC1=CC(=O)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C1=O3038.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Myrsinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9680000000-54fd3d2f599abb3cef562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myrsinone GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-9604400000-6043594d0948b41672882017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myrsinone 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 - Myrsinone 10V, Positive-QTOFsplash10-0002-0190000000-2532f91006677750200d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 20V, Positive-QTOFsplash10-00mn-3960000000-b34136d8a7f0113795952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 40V, Positive-QTOFsplash10-054o-9620000000-34cd3714203286cc40db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 10V, Negative-QTOFsplash10-0006-0090000000-75feb871888a755ab8d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 20V, Negative-QTOFsplash10-052o-0090000000-efd73fe35fab2777ad832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 40V, Negative-QTOFsplash10-0a4i-6980000000-89e1d2710f8ea0eabd082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 10V, Positive-QTOFsplash10-0002-0190000000-1c4491975c34be6e57352021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 20V, Positive-QTOFsplash10-0ka5-8920000000-45b6ee73dc5355b49da22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 40V, Positive-QTOFsplash10-0pba-9400000000-e5b7b7f1625148a180792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 10V, Negative-QTOFsplash10-0006-1090000000-c9d4e7fb5074354944ae2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 20V, Negative-QTOFsplash10-0006-0190000000-bc9915369b6d469d46ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myrsinone 40V, Negative-QTOFsplash10-0a4i-3940000000-e17f02c89ede3d1bba992021-09-24Wishart 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 IDFDB020439
KNApSAcK IDC00057067
Chemspider ID30777500
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound137177207
PDB IDNot Available
ChEBI ID174796
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1885041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.