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Record Information
Version2.0
Created at2022-09-06 14:05:05 UTC
Updated at2022-09-06 14:05:05 UTC
NP-MRD IDNP0232747
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[7-hydroxy-1-(3-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-9-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydro-1h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate
Description(3-{[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[5-hydroxy-14-(3-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-13-yl]oxy}oxan-2-yl)methyl acetate belongs to the class of organic compounds known as steroidal glycosides. (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[7-hydroxy-1-(3-hydroxy-6-methylheptan-2-yl)-9a,11a-dimethyl-9-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydro-1h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate is found in Ornithogalum thyrsoides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[5-hydroxy-14-(3-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-13-yl]oxy}oxan-2-yl)methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[5-hydroxy-14-(3-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0,.0,]heptadecan-13-yl]oxy}oxan-2-yl)methyl acetic acidGenerator
(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[5-hydroxy-14-(3-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl]oxy}oxan-2-yl)methyl acetic acidGenerator
Chemical FormulaC46H78O18
Average Mass919.1120 Da
Monoisotopic Mass918.51882 Da
IUPAC Name(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[5-hydroxy-14-(3-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl]oxy}oxan-2-yl)methyl acetate
Traditional Name(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[5-hydroxy-14-(3-hydroxy-6-methylheptan-2-yl)-2,15-dimethyl-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl]oxy}oxan-2-yl)methyl acetate
CAS Registry NumberNot Available
SMILES
CC(C)CCC(O)C(C)C1C(CC2C3CCC4CC(O)CC(OC5OC(C)C(O)C(O)C5O)C4(C)C3CCC12C)OC1OC(COC(C)=O)C(OC2OCC(O)(CO)C2O)C(O)C1O
InChI Identifier
InChI=1S/C46H78O18/c1-20(2)8-11-29(50)21(3)33-30(61-42-38(55)36(53)39(31(62-42)17-58-23(5)48)64-43-40(56)46(57,18-47)19-59-43)16-28-26-10-9-24-14-25(49)15-32(45(24,7)27(26)12-13-44(28,33)6)63-41-37(54)35(52)34(51)22(4)60-41/h20-22,24-43,47,49-57H,8-19H2,1-7H3
InChI KeyUYLCZACRDJQKFV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ornithogalum thyrsoidesLOTUS 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
  • Diterpene glycoside
  • Cholesterol
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • Steroidal glycoside
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • 22-hydroxysteroid
  • Diterpenoid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Terpene glycoside
  • O-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organooxygen compound
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP0.27ALOGPS
logP0.27ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area283.98 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity223.53 m³·mol⁻¹ChemAxon
Polarizability98.82 ųChemAxon
Number of Rings7ChemAxon
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]