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Record Information
Version2.0
Created at2022-09-03 06:17:26 UTC
Updated at2022-09-03 06:17:26 UTC
NP-MRD IDNP0170182
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,5-bis(acetyloxy)-6-[(4,5-dihydroxy-2-{7',9',13'-trimethyl-5-methylidene-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-3,16'-dioloxy}oxan-3-yl)oxy]-2-methyloxan-3-yl acetate
Description4,5-Bis(acetyloxy)-2-[(4,5-dihydroxy-2-{7',9',13'-trimethyl-5-methylidene-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosan]-18'-ene-3,16'-dioloxy}oxan-3-yl)oxy]-6-methyloxan-3-yl acetate 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. 4,5-bis(acetyloxy)-6-[(4,5-dihydroxy-2-{7',9',13'-trimethyl-5-methylidene-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-3,16'-dioloxy}oxan-3-yl)oxy]-2-methyloxan-3-yl acetate is found in Dracaena angustifolia and Dracaena draco. 4,5-Bis(acetyloxy)-2-[(4,5-dihydroxy-2-{7',9',13'-trimethyl-5-methylidene-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosan]-18'-ene-3,16'-dioloxy}oxan-3-yl)oxy]-6-methyloxan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
4,5-Bis(acetyloxy)-2-[(4,5-dihydroxy-2-{7',9',13'-trimethyl-5-methylidene-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0,.0,.0,]icosan]-18'-ene-3,16'-dioloxy}oxan-3-yl)oxy]-6-methyloxan-3-yl acetic acidGenerator
4,5-Bis(acetyloxy)-2-[(4,5-dihydroxy-2-{7',9',13'-trimethyl-5-methylidene-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-3,16'-dioloxy}oxan-3-yl)oxy]-6-methyloxan-3-yl acetic acidGenerator
Chemical FormulaC50H74O21
Average Mass1011.1210 Da
Monoisotopic Mass1010.47226 Da
IUPAC Name4,5-bis(acetyloxy)-6-[(4,5-dihydroxy-2-{7',9',13'-trimethyl-5-methylidene-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-3,16'-dioloxy}oxan-3-yl)oxy]-2-methyloxan-3-yl acetate
Traditional Name4,5-bis(acetyloxy)-6-[(4,5-dihydroxy-2-{7',9',13'-trimethyl-5-methylidene-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-3,16'-dioloxy}oxan-3-yl)oxy]-2-methyloxan-3-yl acetate
CAS Registry NumberNot Available
SMILES
CC1C2C(CC3C4CC=C5CC(O)CC(OC6OCC(O)C(O)C6OC6OC(C)C(OC(C)=O)C(OC(C)=O)C6OC(C)=O)C5(C)C4CCC23C)OC11OCC(=C)C(OC2OC(C)C(O)C(O)C2O)C1O
InChI Identifier
InChI=1S/C50H74O21/c1-19-17-62-50(44(60)39(19)69-45-38(59)37(58)35(56)21(3)63-45)20(2)34-32(71-50)16-30-28-11-10-26-14-27(54)15-33(49(26,9)29(28)12-13-48(30,34)8)68-46-41(36(57)31(55)18-61-46)70-47-43(67-25(7)53)42(66-24(6)52)40(22(4)64-47)65-23(5)51/h10,20-22,27-47,54-60H,1,11-18H2,2-9H3
InChI KeyQGHYZIGIDBYYEF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dracaena angustifoliaLOTUS Database
Dracaena dracoLOTUS Database
Chemical Taxonomy
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
  • 23-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Ketal
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • 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
logP1.56ALOGPS
logP0.32ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.88ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area294.35 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity239.54 m³·mol⁻¹ChemAxon
Polarizability105.1 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 Compound78180804
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]