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Record Information
Version2.0
Created at2022-09-05 08:01:46 UTC
Updated at2022-09-05 08:01:46 UTC
NP-MRD IDNP0210287
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl acetate
Description5-Hydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl}oxy)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 5-hydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl acetate is found in Astragalus sieversianus. 5-Hydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl}oxy)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
5-Hydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0,.0,.0,]octadecan-6-yl}oxy)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl acetic acidGenerator
5-Hydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl acetic acidGenerator
Chemical FormulaC48H78O18
Average Mass943.1340 Da
Monoisotopic Mass942.51882 Da
IUPAC Name5-hydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl acetate
Traditional Name5-hydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC1OC(OC2C(OC3CCC45CC44CCC6(C)C(C(O)CC6(C)C4CC(OC4OCC(O)C(O)C4O)C5C3(C)C)C3(C)CCC(O3)C(C)(C)O)OCC(O)C2OC(C)=O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C48H78O18/c1-21-30(53)32(55)34(57)40(61-21)65-36-35(62-22(2)49)25(52)19-60-41(36)64-28-11-13-48-20-47(48)15-14-44(7)37(46(9)12-10-29(66-46)43(5,6)58)23(50)17-45(44,8)27(47)16-26(38(48)42(28,3)4)63-39-33(56)31(54)24(51)18-59-39/h21,23-41,50-58H,10-20H2,1-9H3
InChI KeyMWBRLLYGDSLFHT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Astragalus sieversianusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentCucurbitacin glycosides
Alternative Parents
Substituents
  • Cucurbitacin glycoside skeleton
  • Triterpene saponin
  • Triterpene glycoside
  • Cycloartanol-skeleton
  • 9b,19-cyclo-lanostane-skeleton
  • Triterpenoid
  • Cycloartane-skeleton
  • 16-hydroxysteroid
  • Hydroxysteroid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Dialkyl ether
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.93ALOGPS
logP0.036ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area272.98 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity228.64 m³·mol⁻¹ChemAxon
Polarizability101.39 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5166671
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]