5-Geranyloxy-7-methoxycoumarin (CHEM027243)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:35:48 UTC
Update Date2016-11-09 01:18:25 UTC
Accession NumberCHEM027243
Identification
Common Name5-Geranyloxy-7-methoxycoumarin
ClassSmall Molecule
Description5-Geranyloxy-7-methoxycoumarin is found in citrus. 5-Geranyloxy-7-methoxycoumarin is isolated from lime oil (Citrus aurantifolia).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-((3,7-Dimethyl-2,6-octadienyl)oxy)-7-methoxycoumarinHMDB
5-(Geranyloxy)-7-methoxycoumarinHMDB
5-(Geranyloxy)-herniarinHMDB
5-Geranoxy-7-methoxycoumarinHMDB
7-Methoxy-5-geranoxycoumarinHMDB
SAMEHMDB
5-Geranyloxy-7-methoxycoumarinMeSH
Chemical FormulaC20H24O4
Average Molecular Mass328.402 g/mol
Monoisotopic Mass328.167 g/mol
CAS Registry Number7380-39-4
IUPAC Name5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-2H-chromen-2-one
Traditional Name5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxychromen-2-one
SMILESCOC1=CC(OC\C=C(/C)CCC=C(C)C)=C2C=CC(=O)OC2=C1
InChI IdentifierInChI=1S/C20H24O4/c1-14(2)6-5-7-15(3)10-11-23-18-12-16(22-4)13-19-17(18)8-9-20(21)24-19/h6,8-10,12-13H,5,7,11H2,1-4H3/b15-10+
InChI KeyWXUOSNJWDJOHGW-XNTDXEJSSA-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
  • Coumarin
  • Aromatic monoterpenoid
  • Benzopyran
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP5.5ALOGPS
logP4.49ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.4 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-5394000000-4df6b182eab5e78e3f7bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0539000000-65d13c1da33aa0df0a85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n3-5942000000-bfbda5842c74fddf367bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9500000000-aba7df5f0d91fe9f2fefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0329000000-c0a4b6032cdbc8c831f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0912000000-c6dabef31809f1935f77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-50568fb5f1b239e2baafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0903000000-4df63cf8b19e29dc767aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000y-9400000000-b67280a0438715e283a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-8910000000-ac36a849c72510dbf538Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0109000000-e38a893ff4e0d24916f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0096-0911000000-0cf0241b578c276b525dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-0900000000-a8e9a830fdd16c70d1a2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032954
FooDB IDFDB010940
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link5-Geranyloxy-7-methoxycoumarin
Chemspider ID4945553
ChEBI IDNot Available
PubChem Compound ID6441377
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM