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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:59 UTC
Update Date2022-03-07 02:52:23 UTC
HMDB IDHMDB0029983
Secondary Accession Numbers
  • HMDB29983
Metabolite Identification
Common NameEpomusenin B
DescriptionEpomusenin B 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 significant number of articles have been published on Epomusenin B.
Structure
Data?1563861920
SynonymsNot Available
Chemical FormulaC37H66O3
Average Molecular Weight558.9181
Monoisotopic Molecular Weight558.501195978
IUPAC Name5-methyl-3-(12-{3-[(3Z)-octadec-3-en-1-yl]oxiran-2-yl}dodecyl)-2,5-dihydrofuran-2-one
Traditional Name5-methyl-3-(12-{3-[(3Z)-octadec-3-en-1-yl]oxiran-2-yl}dodecyl)-5H-furan-2-one
CAS Registry Number178330-56-8
SMILES
CCCCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCC1=CC(C)OC1=O
InChI Identifier
InChI=1S/C37H66O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-18-21-24-27-30-35-36(40-35)31-28-25-22-19-16-15-17-20-23-26-29-34-32-33(2)39-37(34)38/h21,24,32-33,35-36H,3-20,22-23,25-31H2,1-2H3/b24-21-
InChI KeyMKKPDARISYEUBT-FLFQWRMESA-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
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • 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 Solubility3.7e-10 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.0e-05 g/LALOGPS
logP10.75ALOGPS
logP13.47ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.83 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity173.29 m³·mol⁻¹ChemAxon
Polarizability75.53 ųChemAxon
Number of Rings2ChemAxon
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]+242.39631661259
DarkChem[M-H]-240.82731661259
DeepCCS[M+H]+251.5930932474
DeepCCS[M-H]-248.23730932474
DeepCCS[M-2H]-284.11530932474
DeepCCS[M+Na]+260.40530932474
AllCCS[M+H]+258.032859911
AllCCS[M+H-H2O]+256.732859911
AllCCS[M+NH4]+259.132859911
AllCCS[M+Na]+259.532859911
AllCCS[M-H]-244.032859911
AllCCS[M+Na-2H]-249.632859911
AllCCS[M+HCOO]-255.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epomusenin BCCCCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCC1=CC(C)OC1=O4903.7Standard polar33892256
Epomusenin BCCCCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCC1=CC(C)OC1=O4075.7Standard non polar33892256
Epomusenin BCCCCCCCCCCCCCC\C=C/CCC1OC1CCCCCCCCCCCCC1=CC(C)OC1=O4347.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epomusenin B GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-3394300000-510acfdbdb108b480eb32017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 10V, Positive-QTOFsplash10-0a4i-0030190000-ea075337d9049f6ce53c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 20V, Positive-QTOFsplash10-02bf-1390220000-6d1f2d6d428d3a5b7ea02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 40V, Positive-QTOFsplash10-00nr-3970700000-d93820d20b086c7565ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 10V, Negative-QTOFsplash10-0a4i-0020090000-5a94149daaa1999324132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 20V, Negative-QTOFsplash10-08fr-1040090000-c353391a58a0cc206a5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 40V, Negative-QTOFsplash10-0006-2090000000-ff3cf67cc89baf9b31702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 10V, Negative-QTOFsplash10-0a4i-0000090000-bd117ccc02d36ce8ed1a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 20V, Negative-QTOFsplash10-0a4i-2011090000-f9d01a208a79621795042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 40V, Negative-QTOFsplash10-03di-3314290000-ba3bf359b49fa5ebfabe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 10V, Positive-QTOFsplash10-0a4l-0030190000-85bb3e6db4281ab955412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 20V, Positive-QTOFsplash10-06xx-2000090000-187bb8853b3bf27e9a5a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epomusenin B 40V, Positive-QTOFsplash10-052f-9010000000-1b7367d8730fb9833bc52021-09-23Wishart 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 IDFDB001270
KNApSAcK IDC00044157
Chemspider ID8873424
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10698082
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1812771
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.