Record Information
Version1.0
Creation date2010-04-08 22:10:18 UTC
Update date2025-11-18 23:38:39 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
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
Predicted GC-MS(R)-Oxypeucedanin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1090000000-9a62441281765dc2937c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5090000000-679a16d82a5c237ca58a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5920000000-f745046aa1802d326ac62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-0090000000-0276fe8d4f2cf6a09bf72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0490000000-21dbeed560117c8c53812015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-0910000000-06c5b56d971bd3d4bdb82015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c2309c473ed29ebdc7af2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0090000000-830ea8c1ff4ebfba1bd22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2930000000-9716abcf4cc48c836f412021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-5fe777fd006230f677fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-ad2862cb9064408fae7f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-6890000000-c716dea4ef6d24e6db792021-09-22View Spectrum
NMRNot Available
ChemSpider ID141075
ChEMBL IDCHEMBL1510267
KEGG Compound IDC09282
Pubchem Compound ID160544
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0030622
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 An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Diabetic-macular-edema inhibitor35222 An agent that reduces fluid accumulation in the macula, alleviating vision impairment in diabetic patients. It blocks vascular endothelial growth factor (VEGF) activity, decreasing inflammation and edema, commonly used to treat diabetic macular edema and other retinal disorders.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
LipolyticAn agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
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).