Rhapontigenin (CHEM026687)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:10:23 UTC
Update Date2016-11-09 01:18:19 UTC
Accession NumberCHEM026687
Identification
Common NameRhapontigenin
ClassSmall Molecule
DescriptionRhapontigenin is found in garden rhubarb. Rhapontigenin is isolated from rhizomes of Rheum undulatum (rhubarb) 4-Guanidinobutanoate is a normal metabolite present in low concentrations. Patients with hyperargininemia have an arginase deficiency which leads to blockade of the urea cycle in the last step with several clinical symptoms. Owing to the arginase deficiency this patients accumulate arginine which leads eventually to epileptogenic guanidino compounds (PMID 7752905
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethyleneHMDB
3,3',5-Trihydroxy-4'-methoxystilbeneHMDB
4'-Methoxy-3,3',5-trihydroxystilbeneHMDB
4-Guanidinobutanoic acidHMDB
PontigeninHMDB
Chemical FormulaC15H14O4
Average Molecular Mass258.269 g/mol
Monoisotopic Mass258.089 g/mol
CAS Registry Number500-65-2
IUPAC Name5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
Traditional Name5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
SMILESCOC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1
InChI IdentifierInChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2-
InChI KeyPHMHDRYYFAYWEG-IHWYPQMZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Resorcinol
  • Styrene
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP2.64ALOGPS
logP3.24ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.08ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.92 m³·mol⁻¹ChemAxon
Polarizability26.45 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0490000000-0c7e3c1cc1544fd01557Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0bt9-1001900000-036b5d08a976c1505736Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-cc3e35bd8d646ecf9dddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0590000000-fb36ae977a4e36814287Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fkl-3920000000-c70ef1d9e39f8d23d409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-326dbc7596b8abc29f7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-2c9ea4e757e72cb68c00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2890000000-e1781ac257911d64c7acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-c2a50a42dfada53572a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-96cc8797cb39e482f4e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-0950000000-a841efaa4f3f27296400Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-5436edd338e0c37ed496Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0960000000-b790cc1b715a020f8232Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-0910000000-d0d4c5ff03d7f0ca5185Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031842
FooDB IDFDB008524
Phenol Explorer IDNot Available
KNApSAcK IDC00015562
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRhapontigenin
Chemspider ID9055029
ChEBI IDNot Available
PubChem Compound ID10879760
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C: Guanidino compounds in serum and urine of cirrhotic patients. Metabolism. 1995 May;44(5):584-8.
2. Jung DB, Lee HJ, Jeong SJ, Lee HJ, Lee EO, Kim YC, Ahn KS, Chen CY, Kim SH: Rhapontigenin inhibited hypoxia inducible factor 1 alpha accumulation and angiogenesis in hypoxic PC-3 prostate cancer cells. Biol Pharm Bull. 2011;34(6):850-5.
3. Kim JK, Kim N, Lim YH: Evaluation of the antibacterial activity of rhapontigenin produced from rhapontin by biotransformation against Propionibacterium acnes. J Microbiol Biotechnol. 2010 Jan;20(1):82-7.
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.