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Showing Compound Phellopterin (FDB003977)

Record Information
Version1.0
Creation date2010-04-08 22:06:02 UTC
Update date2019-11-26 02:59:43 UTC
Primary IDFDB003977
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhellopterin
DescriptionPhellopterin is a member of the class of compounds known as 5-methoxypsoralens. 5-methoxypsoralens are psoralens containing a methoxy group attached at the C5 position of the psoralen group. Phellopterin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Phellopterin can be found in lemon, lime, and wild celery, which makes phellopterin a potential biomarker for the consumption of these food products. Phellopterin is a non-carcinogenic (not listed by IARC) potentially toxic compound. The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions (L2157) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs. It activates adrenaline-induced lipolysis and activate ACTH-induced lipolysis (L579) (T3DB).
CAS Number2543-94-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Phellopterinbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP3.56ALOGPS
logP2.99ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.43 m³·mol⁻¹ChemAxon
Polarizability31.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H16O5
IUPAC name4-methoxy-9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3
InChI KeyBMLZFLQMBMYVHG-UHFFFAOYSA-N
Isomeric SMILESCOC1=C2C=CC(=O)OC2=C(OCC=C(C)C)C2=C1C=CO2
Average Molecular Weight300.3059
Monoisotopic Molecular Weight300.099773622
Classification
Description Belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent5-methoxypsoralens
Alternative Parents
Substituents
  • 5-methoxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
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
EI-MSMass Spectrum (Electron Ionization)splash10-0159-5290000000-c6bda842d6e5e427846f2014-09-20View Spectrum
Predicted GC-MSPhellopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00du-1290000000-afef60075ef55803aa37Spectrum
Predicted GC-MSPhellopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-27b231c92641c9254a172021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00lr-1090000000-3ff8129a0f3ae797307c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-1970000000-7c033cb0f0280e448efd2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2039000000-32ef5805aca12f3a0de32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9062000000-8dd30f1ac063a129d47b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9170000000-3d240acaa8ebfceeaf9a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-bb9f27aad8efd0e1848b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0190000000-9dedf08f25531f236d522016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-1590000000-e8fab0a80e5aa7bb1e8f2016-08-03View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC17047
Pubchem Compound ID98608
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPHELLOPTERIN
BIGG IDNot Available
KNApSAcK IDC00030987
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 / Bioactivities
DescriptorIDDefinitionReference
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
lipolyticDUKE
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).