Record Information
Version1.0
Creation date2010-04-08 22:04:56 UTC
Update date2018-01-25 19:27:55 UTC
Primary IDFDB001353
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameUttronin A
DescriptionUttronin a 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. Uttronin a is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Uttronin a can be found in soft-necked garlic, which makes uttronin a a potential biomarker for the consumption of this food product.
CAS Number39941-51-0
Structure
Thumb
Synonyms
SynonymSource
(-)-Desgalactotigoninbiospider
3-O-(beta-Lycotetraosyl)-(25R)-5alpha-spirostan-3beta-olbiospider
Degalactotigonindb_source
Desgalactotigoninbiospider
Tigogenin lycotetraosidedb_source
Uttronin Adb_source
Predicted Properties
PropertyValueSource
Water Solubility1.25 g/LALOGPS
logP-0.32ALOGPS
logP-1.1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)11.76ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area335.06 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity243.11 m³·mol⁻¹ChemAxon
Polarizability110.84 ųChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC50H82O22
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]icosane]oxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C50H82O22/c1-20-7-12-50(64-18-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(62)37(59)41(31(17-53)68-45)69-47-43(71-46-39(61)36(58)34(56)29(15-51)66-46)42(35(57)30(16-52)67-47)70-44-38(60)33(55)27(54)19-63-44/h20-47,51-62H,5-19H2,1-4H3
InChI KeyBJNQXJIQCPPOHN-UHFFFAOYSA-N
Isomeric SMILESCC1C2C(CC3C4CCC5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(CO)C(O)C(OC4OCC(O)C(O)C4O)C3OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11CCC(C)CO1
Average Molecular Weight1035.1729
Monoisotopic Molecular Weight1034.529774308
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
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.01%; H 7.98%; O 34.00%DFC
Melting PointMp 277-280° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -49.6 (c, 0.9 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9203660282-769189275c6032ef4997View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0170-2223950550-95a226d0726553770704View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-7215930620-9ff2aa60933960c13c6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9300220031-745671c65d38c6072c31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-7901520221-0eec93ad52f3f006dd10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-6901520100-51e20be7428ca4124170View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID162401
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHJR73-M:BZQ15-L
EAFUS IDNot Available
Dr. Duke IDDESGALACTOTIGONIN
BIGG IDNot Available
KNApSAcK IDC00032904
HET 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
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
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).