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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:43:23 UTC
Update Date2022-03-07 02:56:09 UTC
HMDB IDHMDB0039309
Secondary Accession Numbers
  • HMDB39309
Metabolite Identification
Common Name9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one
Description9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one.
Structure
Data?1563863352
Synonyms
ValueSource
8-Geranyloxy psoralenChEMBL, HMDB
8-GeranyloxypsoralenHMDB
9-GeranyloxypsoralenHMDB
Xanthotoxol geranyl etherHMDB
5-GeranoxypsoralenMeSH
BergamottinMeSH
Chemical FormulaC21H22O4
Average Molecular Weight338.397
Monoisotopic Molecular Weight338.151809192
IUPAC Name9-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one
Traditional Name9-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}furo[3,2-g]chromen-7-one
CAS Registry Number7437-55-0
SMILES
CC(C)=CCC\C(C)=C\COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
InChI Identifier
InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-19-17(10-12-23-19)13-16-7-8-18(22)25-20(16)21/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
InChI KeySOVNCTNQAWWYAQ-OQLLNIDSSA-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
  • Linear furanocoumarin
  • Furanocoumarin
  • Psoralen
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Monoterpenoid
  • Aromatic monoterpenoid
  • Benzofuran
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point53 - 54 °CNot Available
Boiling Point503.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.034 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.850 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP5.34ALOGPS
logP4.81ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.77 m³·mol⁻¹ChemAxon
Polarizability37.79 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+181.80631661259
DarkChem[M-H]-180.08731661259
DeepCCS[M+H]+179.39830932474
DeepCCS[M-H]-177.0430932474
DeepCCS[M-2H]-210.73730932474
DeepCCS[M+Na]+186.56630932474
AllCCS[M+H]+181.432859911
AllCCS[M+H-H2O]+178.432859911
AllCCS[M+NH4]+184.232859911
AllCCS[M+Na]+185.032859911
AllCCS[M-H]-185.532859911
AllCCS[M+Na-2H]-184.832859911
AllCCS[M+HCOO]-184.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-oneCC(C)=CCC\C(C)=C\COC1=C2OC(=O)C=CC2=CC2=C1OC=C23694.8Standard polar33892256
9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-oneCC(C)=CCC\C(C)=C\COC1=C2OC(=O)C=CC2=CC2=C1OC=C22769.3Standard non polar33892256
9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-oneCC(C)=CCC\C(C)=C\COC1=C2OC(=O)C=CC2=CC2=C1OC=C22876.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gi0-8495000000-d8ee061db6f867b9a9132017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one LC-ESI-qTof , Positive-QTOFsplash10-0bt9-0920000000-c3d63cfbe652764f629a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one , positive-QTOFsplash10-0udj-0950000000-ece121dc18e5faf163012017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 10V, Positive-QTOFsplash10-000i-1439000000-79292069b1ad4ca46fb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 20V, Positive-QTOFsplash10-00kr-6963000000-dd8490d6427f6e280daf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 40V, Positive-QTOFsplash10-0uxr-9420000000-9a184572a7508d5d62212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 10V, Negative-QTOFsplash10-000i-0169000000-29d8d042cce2fcfbef0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 20V, Negative-QTOFsplash10-0udi-0393000000-066716b403edfe52c1ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 40V, Negative-QTOFsplash10-0a4i-0910000000-eb946be92f122e3386f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 10V, Negative-QTOFsplash10-000i-0019000000-c10e3d6f3220c05e72aa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 20V, Negative-QTOFsplash10-0f79-0595000000-402656fb058e83cff4922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 40V, Negative-QTOFsplash10-0udi-1590000000-752253c28c7f829d61672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 10V, Positive-QTOFsplash10-0udi-0090000000-d3876cf6c21fad43493a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 20V, Positive-QTOFsplash10-0f89-9020000000-026297ce3398b8dde9152021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one 40V, Positive-QTOFsplash10-005c-9430000000-75f47fa1e96bea26e1f02021-09-25Wishart 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 IDFDB018859
KNApSAcK IDC00052778
Chemspider ID4476408
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5317564
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1427601
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .