Record Information
Version1.0
Creation date2010-04-08 22:09:23 UTC
Update date2018-05-28 22:49:56 UTC
Primary IDFDB010940
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Geranyloxy-7-methoxycoumarin
DescriptionIsolated from lime oil (Citrus aurantifolia). 5-Geranyloxy-7-methoxycoumarin is found in lime, lemon, and citrus.
CAS Number7380-39-4
Structure
Thumb
Synonyms
SynonymSource
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
Herniarin, 5-(geranyloxy)-biospider
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H24O4
IUPAC name5-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7-methoxy-2H-chromen-2-one
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
Isomeric SMILESCOC1=CC(OC\C=C(/C)CCC=C(C)C)=C2C=CC(=O)OC2=C1
Average Molecular Weight328.4022
Monoisotopic Molecular Weight328.167459256
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.15%; H 7.37%; O 19.49%DFC
Melting PointMp 86-87°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-5394000000-4df6b182eab5e78e3f7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0539000000-65d13c1da33aa0df0a85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n3-5942000000-bfbda5842c74fddf367bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9500000000-aba7df5f0d91fe9f2fefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0329000000-c0a4b6032cdbc8c831f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0912000000-c6dabef31809f1935f77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-50568fb5f1b239e2baafView in MoNA
ChemSpider ID4945553
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6441377
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32954
CRC / DFC (Dictionary of Food Compounds) IDGZJ39-P:FWN03-O
EAFUS IDNot Available
Dr. Duke ID5-GERANYL-OXY-7-METHOXY-COUMARIN|5-GERANOXY-7-METHOXYCOUMARIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).