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Record Information
Version2.0
Created at2022-09-05 05:25:14 UTC
Updated at2022-09-05 05:25:15 UTC
NP-MRD IDNP0208419
Secondary Accession NumbersNone
Natural Product Identification
Common Name14'-[(3-{[3,5-bis(acetyloxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl)oxy]-3,16'-dihydroxy-7'-(hydroxymethyl)-5,13'-dimethyl-3'-oxo-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-2'(9'),18'-dien-4-yl acetate
Description14'-[(3-{[3,5-Bis(acetyloxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl)oxy]-3,16'-dihydroxy-7'-(hydroxymethyl)-5,13'-dimethyl-3'-oxo-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane]-2'(9'),18'-dien-4-yl acetate belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. 14'-[(3-{[3,5-bis(acetyloxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl)oxy]-3,16'-dihydroxy-7'-(hydroxymethyl)-5,13'-dimethyl-3'-oxo-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-2'(9'),18'-dien-4-yl acetate is found in Trillium tschonoskii. 14'-[(3-{[3,5-Bis(acetyloxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl)oxy]-3,16'-dihydroxy-7'-(hydroxymethyl)-5,13'-dimethyl-3'-oxo-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane]-2'(9'),18'-dien-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
14'-[(3-{[3,5-bis(acetyloxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl)oxy]-3,16'-dihydroxy-7'-(hydroxymethyl)-5,13'-dimethyl-3'-oxo-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0,.0,.0,]icosane]-2'(9'),18'-dien-4-yl acetic acidGenerator
14'-[(3-{[3,5-bis(acetyloxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl)oxy]-3,16'-dihydroxy-7'-(hydroxymethyl)-5,13'-dimethyl-3'-oxo-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-2'(9'),18'-dien-4-yl acetic acidGenerator
Chemical FormulaC43H60O19
Average Mass880.9340 Da
Monoisotopic Mass880.37288 Da
IUPAC Name14'-[(3-{[3,5-bis(acetyloxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl)oxy]-3,16'-dihydroxy-7'-(hydroxymethyl)-5,13'-dimethyl-3'-oxo-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-2'(9'),18'-dien-4-yl acetate
Traditional Name14'-[(3-{[3,5-bis(acetyloxy)-4-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl)oxy]-3,16'-dihydroxy-7'-(hydroxymethyl)-5,13'-dimethyl-3'-oxo-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-2'(9'),18'-dien-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC1COC2(OC3C(C2CO)C2=C(C4CC=C5CC(O)CC(OC6OCC(O)C(O)C6OC6OC(C)C(OC(C)=O)C(O)C6OC(C)=O)C5(C)C4CC2)C3=O)C(O)C1OC(C)=O
InChI Identifier
InChI=1S/C43H60O19/c1-16-14-55-43(39(53)34(16)57-18(3)45)26(13-44)30-24-9-10-25-23(29(24)32(51)36(30)62-43)8-7-21-11-22(48)12-28(42(21,25)6)60-40-37(31(50)27(49)15-54-40)61-41-38(59-20(5)47)33(52)35(17(2)56-41)58-19(4)46/h7,16-17,22-23,25-28,30-31,33-41,44,48-50,52-53H,8-15H2,1-6H3
InChI KeyVGZYTSQXIMLHHW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Trillium tschonoskiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Steroidal glycoside
  • 23-hydroxysteroid
  • 21-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 15-oxosteroid
  • Delta-5-steroid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Ketal
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • 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
logP0.7ALOGPS
logP-0.87ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area272.73 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity207.22 m³·mol⁻¹ChemAxon
Polarizability89.71 ųChemAxon
Number of Rings8ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]