Diosgenin 3-[glucosyl-(1->4)-[glucopyranosyl-(1->6)]-glucopyranosyl-(1->4)-rhamnosyl-(1->4)-[rhamnosyl-(1->2)]-glucoside] (CHEM031438)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:39:13 UTC
Update Date2016-11-09 01:19:16 UTC
Accession NumberCHEM031438
Identification
Common NameDiosgenin 3-[glucosyl-(1->4)-[glucopyranosyl-(1->6)]-glucopyranosyl-(1->4)-rhamnosyl-(1->4)-[rhamnosyl-(1->2)]-glucoside]
ClassSmall Molecule
DescriptionIsolated from Allium vineale (wild garlic). Diosgenin 3-[glucosyl-(1->4)-[glucopyranosyl-(1->6)]-glucopyranosyl-(1->4)-rhamnosyl-(1->4)-[rhamnosyl-(1->2)]-glucoside] is found in onion-family vegetables.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC63H102O31
Average Molecular Mass1355.465 g/mol
Monoisotopic Mass1354.641 g/mol
CAS Registry Number121372-77-8
IUPAC Name2-({6-[(4,5-dihydroxy-6-{[4-hydroxy-2-(hydroxymethyl)-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-2-methyloxan-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name2-({6-[(4,5-dihydroxy-6-{[4-hydroxy-2-(hydroxymethyl)-6-{5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-2-methyloxan-3-yl)oxy]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
SMILESCC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C)C(OC4OC(COC5OC(CO)C(O)C(O)C5O)C(OC5OC(CO)C(O)C(O)C5O)C(O)C4O)C(O)C3O)C(O)C2OC2OC(C)C(O)C(O)C2O)OC11CCC(C)CO1
InChI IdentifierInChI=1S/C63H102O31/c1-22-9-14-63(82-20-22)23(2)36-31(94-63)16-30-28-8-7-26-15-27(10-12-61(26,5)29(28)11-13-62(30,36)6)85-60-54(93-56-46(76)40(70)37(67)24(3)83-56)50(80)52(34(19-66)88-60)91-57-48(78)43(73)51(25(4)84-57)90-59-49(79)44(74)53(92-58-47(77)42(72)39(69)33(18-65)87-58)35(89-59)21-81-55-45(75)41(71)38(68)32(17-64)86-55/h7,22-25,27-60,64-80H,8-21H2,1-6H3
InChI KeyMVJHGXUJWDGPHK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal saponins
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility4.65 g/LALOGPS
logP-0.3ALOGPS
logP-3.6ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)11.61ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count31ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area473.13 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity311.66 m³·mol⁻¹ChemAxon
Polarizability140.53 ųChemAxon
Number of Rings12ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014u-4829410630-9f2e366d6e54ad94d4c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01dj-7726640930-92b7f60a17dbaae7c5f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01dj-9416430610-f51431cd79391338fa97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01p9-6916200210-db25b251c8474f9e3d87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-3914210210-ae5b61bf2a8ad49c5744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-6922520300-b11e13bff5313e1ddca3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0119000000-380de4b8e340b3947dcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-5496001000-813bec004b4b8b63ff14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9422044400-681696c4f3b54bf4c7ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6u-1519101100-dcae4911f1792428ec96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ads-1509120200-468b8192512c39e9a916Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-5965100000-8325ce29ecfa3b0e80a2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDHMDB0038022
FooDB IDFDB017231
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID14393909
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM