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Showing Compound 9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen (FDB018555)

Record Information
Version1.0
Creation date2010-04-08 22:13:47 UTC
Update date2019-11-26 03:16:19 UTC
Primary IDFDB018555
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen
Description9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. 9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen has been detected, but not quantified in, citrus. This could make 9-hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen.
CAS Number69239-53-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Protorifamycin IHMDB
4-[3,7-Dimethylocta-2,6-dienoxy]-9-methoxyfuro[3,2-g]chromen-7-onemanual
9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralenmanual
9-Hydroxy-4-O-(3,7-dimethyl-2,6-octadienyloxy)-psoralenmanual
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP4.94ALOGPS
logP4.65ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.9 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.24 m³·mol⁻¹ChemAxon
Polarizability40.68 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H24O5
IUPAC name4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-9-methoxy-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C22H24O5/c1-14(2)6-5-7-15(3)10-12-25-19-16-8-9-18(23)27-21(16)22(24-4)20-17(19)11-13-26-20/h6,8-11,13H,5,7,12H2,1-4H3/b15-10+
InChI KeyOQHQALGVQDTJDN-XNTDXEJSSA-N
Isomeric SMILESCOC1=C2OC(=O)C=CC2=C(OC\C=C(/C)CCC=C(C)C)C2=C1OC=C2
Average Molecular Weight368.423
Monoisotopic Molecular Weight368.162373878
Classification
Description Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent8-methoxypsoralens
Alternative Parents
Substituents
  • 8-methoxypsoralen
  • Terpene lactone
  • Aromatic monoterpenoid
  • Benzopyran
  • Monoterpenoid
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.72%; H 6.57%; O 21.71%DFC
Melting PointMp 74.5-75.5°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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ukl-6479000000-c570fee77df7a705ca90Spectrum
Predicted GC-MS9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0319000000-0d729bc45ebd424287ea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067r-7956000000-9dd9639b04a764433fa62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9231000000-8852b3c18c530af8f13c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-acf1520a0d3e19084f972016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0294000000-0bd6f5a975b7d768015d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-1970000000-43a48095b683bcd8545d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-7b7777091d83071e87812021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01c0-0395000000-9a20284d011cc2c8affd2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0j4r-3490000000-19917ec649e2db5844eb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-f8867cbe344d3e6bacad2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-6090000000-9c93ca565dbaaf7ecfc22021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9170000000-9e4d88d23771b43a33092021-09-25View Spectrum
NMRNot Available
ChemSpider ID4944685
ChEMBL IDCHEMBL1934195
KEGG Compound IDNot Available
Pubchem Compound ID6440422
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39057
CRC / DFC (Dictionary of Food Compounds) IDKDD33-Z:LLP00-K
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH 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