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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:49:37 UTC
Update Date2022-03-07 02:53:58 UTC
HMDB IDHMDB0034049
Secondary Accession Numbers
  • HMDB34049
Metabolite Identification
Common NamePachyrrhizin
DescriptionPachyrrhizin belongs to the class of organic compounds known as isoflav-3-enones. These are flavonoids with a structure based on an isoflav-3-ene skeleton bearing an oxo-group at position C2. Thus, pachyrrhizin is considered to be a flavonoid. Pachyrrhizin has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make pachyrrhizin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pachyrrhizin.
Structure
Data?1563862501
Synonyms
ValueSource
6-(2-Methoxy-4,5-methylenedioxyphenyl)furocoumarinHMDB
6-(6-Methoxy-1,3-benzodioxol-5-yl)-7H-furo[3,2-g][1]benzopyran-7-one, 9ciHMDB
NeorautoneHMDB
PachyrhizinHMDB
Chemical FormulaC19H12O6
Average Molecular Weight336.295
Monoisotopic Molecular Weight336.063388116
IUPAC Name6-(6-methoxy-2H-1,3-benzodioxol-5-yl)-7H-furo[3,2-g]chromen-7-one
Traditional Namepachyrrhizin
CAS Registry Number10091-01-7
SMILES
COC1=CC2=C(OCO2)C=C1C1=CC2=C(OC1=O)C=C1OC=CC1=C2
InChI Identifier
InChI=1S/C19H12O6/c1-21-16-8-18-17(23-9-24-18)6-12(16)13-5-11-4-10-2-3-22-14(10)7-15(11)25-19(13)20/h2-8H,9H2,1H3
InChI KeyPENSQRMNZZWMGV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflav-3-enones. These are flavonoids with a structure based on an isoflav-3-ene skeleton bearing an oxo-group at position C2.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-3-enes
Direct ParentIsoflav-3-enones
Alternative Parents
Substituents
  • Furanoisoflavonoid skeleton
  • Isoflav-3-enone skeleton
  • Furanocoumarin
  • Linear furanocoumarin
  • Psoralen
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzodioxole
  • Benzofuran
  • Anisole
  • Pyranone
  • Alkyl aryl ether
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Ether
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point207 - 209 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.057 g/LALOGPS
logP3.15ALOGPS
logP3.08ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area67.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity87.07 m³·mol⁻¹ChemAxon
Polarizability33.91 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.01631661259
DarkChem[M-H]-179.00331661259
DeepCCS[M+H]+174.18730932474
DeepCCS[M-H]-171.82930932474
DeepCCS[M-2H]-205.90430932474
DeepCCS[M+Na]+181.13130932474
AllCCS[M+H]+177.432859911
AllCCS[M+H-H2O]+173.932859911
AllCCS[M+NH4]+180.732859911
AllCCS[M+Na]+181.632859911
AllCCS[M-H]-179.232859911
AllCCS[M+Na-2H]-178.032859911
AllCCS[M+HCOO]-176.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PachyrrhizinCOC1=CC2=C(OCO2)C=C1C1=CC2=C(OC1=O)C=C1OC=CC1=C24407.2Standard polar33892256
PachyrrhizinCOC1=CC2=C(OCO2)C=C1C1=CC2=C(OC1=O)C=C1OC=CC1=C23017.9Standard non polar33892256
PachyrrhizinCOC1=CC2=C(OCO2)C=C1C1=CC2=C(OC1=O)C=C1OC=CC1=C23210.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pachyrrhizin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-1169000000-374550ff8e39af1c9c852017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pachyrrhizin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pachyrrhizin 40V, Positive-QTOFsplash10-00rj-0390000000-1710b32ae753b46b88132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pachyrrhizin 10V, Positive-QTOFsplash10-000i-0119000000-4f0ad9ad0587fe29383b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pachyrrhizin 20V, Positive-QTOFsplash10-0adr-0269000000-879536834d24c29c7d062021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 10V, Positive-QTOFsplash10-000i-0009000000-b2c4c976a55d762d03852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 20V, Positive-QTOFsplash10-000i-0019000000-9061fae0bde6db8ff7622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 40V, Positive-QTOFsplash10-06rl-1092000000-0b627b170378b487616a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 10V, Negative-QTOFsplash10-000i-0019000000-e530bf3b45770445ae2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 20V, Negative-QTOFsplash10-000i-0039000000-6c73fd50a072b29778312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 40V, Negative-QTOFsplash10-01rf-1091000000-377bf81d2f33da78938a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 10V, Negative-QTOFsplash10-000i-0009000000-cf75db3fcf76086bc0a22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 20V, Negative-QTOFsplash10-000i-0009000000-cf75db3fcf76086bc0a22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 40V, Negative-QTOFsplash10-0a4i-0093000000-1794bdf37da1acff59532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 10V, Positive-QTOFsplash10-000i-0009000000-a487dc1a344a663536352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 20V, Positive-QTOFsplash10-000i-0009000000-1ef859e68262f16ed0332021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pachyrrhizin 40V, Positive-QTOFsplash10-0a4l-0096000000-ff36862384daa809ffbd2021-09-25Wishart LabView Spectrum
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 IDFDB012293
KNApSAcK IDC00009783
Chemspider ID91510
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101277
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1840061
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.. .