Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2019-11-26 03:07:20 UTC
Primary IDFDB012667
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePrangolarin
Description(r)-oxypeucedanin, also known as hishigado or phosphine, is a member of the class of compounds known as psoralens. Psoralens are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one (r)-oxypeucedanin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (r)-oxypeucedanin can be found in carrot, lemon, parsley, and wild carrot, which makes (r)-oxypeucedanin a potential biomarker for the consumption of these food products.
CAS Number737-52-0
Structure
Thumb
Synonyms
SynonymSource
Amgard CPCHMDB
Amgard CPC 405HMDB
Black phosphorusHMDB
Bonide blue death rat killerHMDB
Common sense cockroach and rat preparationsHMDB
ECO2fumeHMDB
Exolit 385HMDB
Exolit 405HMDB
Exolit LPKNHMDB
Exolit LPKN 275HMDB
Exolit RP 605HMDB
Exolit RP 650HMDB
Exolit RP 652HMDB
Exolit RP 654HMDB
Exolit VPK-N 361HMDB
FR-T 2 (Element)HMDB
Gas-ex-bHMDB
HishigadoHMDB
Hishigado apHMDB
Hishigado CPHMDB
Hishigado NP 10HMDB
Hishigado PLHMDB
Hostaflam RP 602HMDB
Hostaflam RP 614HMDB
Hostaflam RP 622HMDB
Hostaflam RP 654HMDB
Nova sol R 20HMDB
Novaexcel 140HMDB
Novaexcel 150HMDB
Novaexcel F 5HMDB
Novaexcel ST 100HMDB
Novaexcel ST 140HMDB
Novaexcel ST 300HMDB
Novared 120ufHMDB
Novared 120ufaHMDB
Novared 120vfaHMDB
Novared 140HMDB
Novared 280HMDB
Novared C 120HMDB
Novared F 5HMDB
OxypeucedaninHMDB
PhosphineHMDB
Phosphine (fumigant)HMDB
Phosphorus (red)HMDB
PHOSPHORUS metal, 99.999%, redHMDB
Phosphorus, amorphousHMDB
Phosphorus, whiteHMDB
Phosphorus-31HMDB
Rat-nipHMDB
Oxypeucadanin, (R)-(+)-isomerHMDB
Oxypeucadanin, (S)-(-)-isomerHMDB
Oxypeucadanin hydrateHMDB
OxypeucadaninHMDB
OxypeucedarinHMDB
4-(2,3-Dihydroxy-3-methylbutoxy)-7H-furo(3,2-g)(1)benzopyran-7-oneHMDB
Prangolarindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP2.79ALOGPS
logP2.32ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.2 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.65 m³·mol⁻¹ChemAxon
Polarizability28.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H14O5
IUPAC name4-[(3,3-dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C16H14O5/c1-16(2)13(21-16)8-19-15-9-3-4-14(17)20-12(9)7-11-10(15)5-6-18-11/h3-7,13H,8H2,1-2H3
InChI KeyQTAGQHZOLRFCBU-UHFFFAOYSA-N
Isomeric SMILESCC1(C)OC1COC1=C2C=CC(=O)OC2=CC2=C1C=CO2
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
Classification
Description Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
Alternative Parents
Substituents
  • Psoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.13%; H 4.93%; O 27.94%DFC
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
Predicted GC-MS(R)-Oxypeucedanin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fdo-9370000000-ba212a82c604298e7a11Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-0090000000-0276fe8d4f2cf6a09bf7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0490000000-21dbeed560117c8c5381Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-0910000000-06c5b56d971bd3d4bdb8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c2309c473ed29ebdc7afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0090000000-830ea8c1ff4ebfba1bd2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2930000000-9716abcf4cc48c836f41Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1090000000-9a62441281765dc2937cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5090000000-679a16d82a5c237ca58aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5920000000-f745046aa1802d326ac6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-5fe777fd006230f677faSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-ad2862cb9064408fae7fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-6890000000-c716dea4ef6d24e6db79Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHJP78-H:HJP78-H
EAFUS IDNot Available
Dr. Duke IDOXYPEUCEDANIN
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 / Bioactivities
DescriptorIDDefinitionReference
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
diabetic-macular-edema inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
lipolyticDUKE
mutagenicDUKE
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).