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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:00 UTC
Update Date2019-07-23 06:06:53 UTC
HMDB IDHMDB0030622
Secondary Accession Numbers
  • HMDB30622
Metabolite Identification
Common Name(R)-Oxypeucedanin
Description(R)-Oxypeucedanin, also known as hishigado or amgard CPC, 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 (R)-Oxypeucedanin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (R)-Oxypeucedanin is found, on average, in the highest concentration within parsley (R)-Oxypeucedanin has also been detected, but not quantified in, a few different foods, such as carrots, lemons, and wild carrots. This could make (R)-oxypeucedanin a potential biomarker for the consumption of these foods (R)-Oxypeucedanin is a potentially toxic compound.
Structure
Data?1563862013
Synonyms
ValueSource
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
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name4-[(3,3-dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one
Traditional Name4-[(3,3-dimethyloxiran-2-yl)methoxy]furo[3,2-g]chromen-7-one
CAS Registry Number3173-02-2
SMILES
CC1(C)OC1COC1=C2C=CC(=O)OC2=CC2=C1C=CO2
InChI Identifier
InChI=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
Chemical Taxonomy
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
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point104 - 105 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fdo-9370000000-ba212a82c604298e7a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1090000000-9a62441281765dc2937cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5090000000-679a16d82a5c237ca58aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5920000000-f745046aa1802d326ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-0090000000-0276fe8d4f2cf6a09bf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0490000000-21dbeed560117c8c5381Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-0910000000-06c5b56d971bd3d4bdb8Spectrum
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 IDFDB012667
KNApSAcK IDNot Available
Chemspider ID141075
KEGG Compound IDC09282
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160544
PDB IDNot Available
ChEBI ID1034151
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kavanaugh KM, Aisen AM, Fechner KP, Wroblewski L, Chenevert TL, Buda AJ: Effects of diltiazem on phosphate metabolism in ischemic and reperfused myocardium using phosphorus31 nuclear magnetic resonance spectroscopy in vivo. Am Heart J. 1989 Dec;118(6):1210-9. [PubMed:2589162 ]
  2. Kavanaugh KM, Aisen AM, Fechner KP, Chenevert TL, Dunham WR, Buda AJ: Regional metabolism during coronary occlusion, reperfusion, and reocclusion using phosphorus31 nuclear magnetic resonance spectroscopy in the intact rabbit. Am Heart J. 1989 Jan;117(1):53-9. [PubMed:2911990 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:
GSTP1
Uniprot ID:
P09211
Molecular weight:
23355.625
Reactions
(R)-Oxypeucedanin → 2-amino-4-({1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[3-hydroxy-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-4-yl}oxy)butan-2-yl]sulfanyl}ethyl}-C-hydroxycarbonimidoyl)butanoic aciddetails
(R)-Oxypeucedanin → 2-amino-4-({1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[3-hydroxy-2-methyl-4-({7-oxo-7H-furo[3,2-g]chromen-4-yl}oxy)butan-2-yl]sulfanyl}ethyl}-C-hydroxycarbonimidoyl)butanoic aciddetails