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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:16 UTC
Update Date2022-03-07 02:53:29 UTC
HMDB IDHMDB0032850
Secondary Accession Numbers
  • HMDB32850
Metabolite Identification
Common NameMuricadienin
DescriptionMuricadienin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review a small amount of articles have been published on Muricadienin.
Structure
Data?1563862316
Synonyms
ValueSource
5-Methyl-3-(13,17-triacontadienyl)-2(5H)-furanoneHMDB
MuricadieninMeSH
Chemical FormulaC35H62O2
Average Molecular Weight514.8656
Monoisotopic Molecular Weight514.474981228
IUPAC Name5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]-2,5-dihydrofuran-2-one
Traditional Name5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]-5H-furan-2-one
CAS Registry Number206131-77-3
SMILES
CCCCCCCCCCCC\C=C/CC\C=C/CCCCCCCCCCCCC1=CC(C)OC1=O
InChI Identifier
InChI=1S/C35H62O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-34-32-33(2)37-35(34)36/h14-15,18-19,32-33H,3-13,16-17,20-31H2,1-2H3/b15-14-,19-18-
InChI KeyZZXWNKPYSIVFNM-XUWLZAGCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentAnnonaceous acetogenins
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
  • 2-furanone
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.8e-10 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.6e-06 g/LALOGPS
logP10.82ALOGPS
logP13.52ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity165.69 m³·mol⁻¹ChemAxon
Polarizability69.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
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]+240.06831661259
DarkChem[M-H]-240.46731661259
DeepCCS[M+H]+244.13330932474
DeepCCS[M-H]-241.33230932474
DeepCCS[M-2H]-276.45530932474
DeepCCS[M+Na]+252.74530932474
AllCCS[M+H]+243.332859911
AllCCS[M+H-H2O]+241.832859911
AllCCS[M+NH4]+244.632859911
AllCCS[M+Na]+245.032859911
AllCCS[M-H]-243.232859911
AllCCS[M+Na-2H]-248.832859911
AllCCS[M+HCOO]-255.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MuricadieninCCCCCCCCCCCC\C=C/CC\C=C/CCCCCCCCCCCCC1=CC(C)OC1=O4660.4Standard polar33892256
MuricadieninCCCCCCCCCCCC\C=C/CC\C=C/CCCCCCCCCCCCC1=CC(C)OC1=O3852.8Standard non polar33892256
MuricadieninCCCCCCCCCCCC\C=C/CC\C=C/CCCCCCCCCCCCC1=CC(C)OC1=O3982.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Muricadienin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4983300000-81a1c0ad8cac4ae91cc52017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 10V, Positive-QTOFsplash10-014i-0010590000-1a00977c4a6e7f8717c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 20V, Positive-QTOFsplash10-016r-0230900000-6f62403259f3e4a78c1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 40V, Positive-QTOFsplash10-004l-1111900000-649c6817199023153adb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 10V, Negative-QTOFsplash10-03di-1000390000-160e257073e96c51a42f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 20V, Negative-QTOFsplash10-03xr-2000970000-f9feffc5b9993b10e39d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 40V, Negative-QTOFsplash10-014l-3000900000-967968f3949f12664d552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 10V, Positive-QTOFsplash10-014i-0110390000-0718adbac60e03ca57892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 20V, Positive-QTOFsplash10-014i-2000930000-cecdcde58f8728028acc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 40V, Positive-QTOFsplash10-0536-9103200000-34cda4cd96a13d834b1e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 10V, Negative-QTOFsplash10-03di-0000090000-8244ab794a0c757ef01c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 20V, Negative-QTOFsplash10-03di-2000490000-74a6e85be179f38fa3dc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Muricadienin 40V, Negative-QTOFsplash10-014i-4501900000-1e2ba2c24c13f887088a2021-09-25Wishart 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 IDFDB010827
KNApSAcK IDC00053512
Chemspider ID35013506
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751334
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1832091
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.