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Showing Compound Dioscin (FDB000366)

Record Information
Version1.0
Creation date2010-04-08 22:04:32 UTC
Update date2019-11-26 02:54:40 UTC
Primary IDFDB000366
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDioscin
DescriptionDioscin is a member of the class of compounds known as steroidal saponins. Steroidal saponins are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Dioscin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Dioscin can be found in fenugreek and yam, which makes dioscin a potential biomarker for the consumption of these food products.
CAS Number19057-60-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Collettiside IIIdb_source
Dioscindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.49ALOGPS
logP1.71ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)11.88ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area235.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity214.42 m³·mol⁻¹ChemAxon
Polarizability95.54 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H72O16
IUPAC name2-[(2-{[4,5-dihydroxy-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}oxan-3-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl)oxy]-6-methyloxane-3,4,5-triol
InChI IdentifierInChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-41-37(53)35(51)38(29(17-46)58-41)59-42-39(34(50)32(48)22(4)56-42)60-40-36(52)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3
InChI KeySLKDWTBGYHJQNM-UHFFFAOYSA-N
Isomeric SMILESCC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(C)C(O)C(O)C3OC3OC(C)C(O)C(O)C3O)C(O)C2O)OC11CCC(C)CO1
Average Molecular Weight869.0436
Monoisotopic Molecular Weight868.482036256
Classification
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 Parents
Substituents
  • Steroidal saponin
  • Triterpenoid
  • Spirostane skeleton
  • Oligosaccharide
  • Delta-5-steroid
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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 62.19%; H 8.35%; O 29.46%DFC
Melting PointMp 275-277° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]13D -115 (c, 0.4 in EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02ta-9514541770-7f00e1e17ab4e4a89f1c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4822940420-da29e01d13a6008fb0172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-6801920000-9824d38aa6611cb03e6c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-6205880970-ff9b873bf9c3b967ef032016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-3223960200-6d0baad0286e0d7615dd2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9404730010-832577c629777bc7f4562016-06-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08897
Pubchem Compound ID16072386
Pubchem Substance IDNot Available
ChEBI ID492973
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBL90-H:BBC02-B
EAFUS IDNot Available
Dr. Duke IDDIOSCIN
BIGG IDNot Available
KNApSAcK IDC00003575
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
amebicide33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti gliomicDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
hemolyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
piscicideDUKE
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.