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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:51 UTC
Update Date2022-03-07 02:52:37 UTC
HMDB IDHMDB0030597
Secondary Accession Numbers
  • HMDB30597
Metabolite Identification
Common NameUmbelliprenin
DescriptionUmbelliprenin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on Umbelliprenin.
Structure
Data?1563862009
Synonyms
ValueSource
Umbelliferone farnesyl etherHMDB
Chemical FormulaC24H30O3
Average Molecular Weight366.4932
Monoisotopic Molecular Weight366.219494826
IUPAC Name7-{[(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy}-2H-chromen-2-one
Traditional Name7-{[(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy}chromen-2-one
CAS Registry Number23838-17-7
SMILES
CC(C)=CCC\C(C)=C/CC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1
InChI Identifier
InChI=1S/C24H30O3/c1-18(2)7-5-8-19(3)9-6-10-20(4)15-16-26-22-13-11-21-12-14-24(25)27-23(21)17-22/h7,9,11-15,17H,5-6,8,10,16H2,1-4H3/b19-9-,20-15+
InChI KeyGNMUGVNEWCZUAA-SGRLLCBQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point61 - 63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00096 g/LALOGPS
logP7.18ALOGPS
logP6.31ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity114.74 m³·mol⁻¹ChemAxon
Polarizability43.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.61231661259
DarkChem[M-H]-188.55431661259
DeepCCS[M+H]+198.13630932474
DeepCCS[M-H]-195.70230932474
DeepCCS[M-2H]-230.00930932474
DeepCCS[M+Na]+206.26530932474
AllCCS[M+H]+196.032859911
AllCCS[M+H-H2O]+193.332859911
AllCCS[M+NH4]+198.532859911
AllCCS[M+Na]+199.232859911
AllCCS[M-H]-194.332859911
AllCCS[M+Na-2H]-194.232859911
AllCCS[M+HCOO]-194.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
UmbellipreninCC(C)=CCC\C(C)=C/CC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C13844.2Standard polar33892256
UmbellipreninCC(C)=CCC\C(C)=C/CC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C12970.8Standard non polar33892256
UmbellipreninCC(C)=CCC\C(C)=C/CC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C13118.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Umbelliprenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbi-5794000000-bc0b6dccdca6586737462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Umbelliprenin 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 - Umbelliprenin 10V, Positive-QTOFsplash10-014i-0529000000-f5905d355686778c017e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 20V, Positive-QTOFsplash10-0cdi-2953000000-e35bcd49e0527105c61f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 40V, Positive-QTOFsplash10-0n90-7901000000-04a3af8a46874458db452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 10V, Negative-QTOFsplash10-014i-0309000000-873e26194d07c44543072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 20V, Negative-QTOFsplash10-03xr-0903000000-4fea4ca956c4962d292c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 40V, Negative-QTOFsplash10-014i-1900000000-fef678a23b902ef78c982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 10V, Negative-QTOFsplash10-03di-0902000000-7838adba25de95749fa72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 20V, Negative-QTOFsplash10-03di-0901000000-09b3f235b42a2e67f2a62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 40V, Negative-QTOFsplash10-0159-0900000000-01dcfc98c596b1cc74d72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 10V, Positive-QTOFsplash10-03xr-1729000000-711bcac4a705513fe8a92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 20V, Positive-QTOFsplash10-03di-3901000000-3739853754c2cf79390a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Umbelliprenin 40V, Positive-QTOFsplash10-03dl-5900000000-dfb15b92e786e1dd311f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB002491
KNApSAcK IDC00034737
Chemspider ID1400851
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1781412
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. 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.