You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:24:38 UTC
Update Date2019-07-23 06:28:25 UTC
HMDB IDHMDB0039057
Secondary Accession Numbers
  • HMDB39057
Metabolite Identification
Common Name9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen
Description9-Hydroxy-4-(3,7-dimethyl-2,6-octadienyloxy)-psoralen, also known as protorifamycin I, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 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.
Structure
Data?1563863305
Synonyms
ValueSource
Protorifamycin IHMDB
Chemical FormulaC22H24O5
Average Molecular Weight368.423
Monoisotopic Molecular Weight368.162373878
IUPAC Name4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-9-methoxy-7H-furo[3,2-g]chromen-7-one
Traditional Name4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-9-methoxyfuro[3,2-g]chromen-7-one
CAS Registry Number69239-53-8
SMILES
COC1=C2OC(=O)C=CC2=C(OC\C=C(/C)CCC=C(C)C)C2=C1OC=C2
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point74.5 - 75.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ukl-6479000000-c570fee77df7a705ca90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0319000000-0d729bc45ebd424287eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067r-7956000000-9dd9639b04a764433fa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9231000000-8852b3c18c530af8f13cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-acf1520a0d3e19084f97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0294000000-0bd6f5a975b7d768015dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-1970000000-43a48095b683bcd8545dSpectrum
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 IDFDB018555
KNApSAcK IDNot Available
Chemspider ID4944685
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6440422
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .