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Record Information
Version2.0
Created at2022-09-10 14:24:20 UTC
Updated at2022-09-10 14:24:20 UTC
NP-MRD IDNP0301441
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate
DescriptionSagittatoside C belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. 2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate is found in Epimedium sagittatum. Sagittatoside C is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetic acidGenerator
Chemical FormulaC35H42O16
Average Mass718.7050 Da
Monoisotopic Mass718.24729 Da
IUPAC Name2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate
Traditional Name2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=C1)C1=C(OC2OC(C)C(O)C(OC(C)=O)C2OC2OC(CO)C(O)C(O)C2O)C(=O)C2=C(O)C=C(O)C(CC=C(C)C)=C2O1
InChI Identifier
InChI=1S/C35H42O16/c1-14(2)6-11-19-20(38)12-21(39)23-26(42)32(29(49-30(19)23)17-7-9-18(45-5)10-8-17)50-35-33(31(47-16(4)37)24(40)15(3)46-35)51-34-28(44)27(43)25(41)22(13-36)48-34/h6-10,12,15,22,24-25,27-28,31,33-36,38-41,43-44H,11,13H2,1-5H3
InChI KeyQGVUYZAEBBWPRU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Epimedium sagittatumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassN-alkylpyrrolidines
Direct ParentN-alkylpyrrolidines
Alternative Parents
Substituents
  • N-alkylpyrrolidine
  • Dithiolane
  • 1,2-dithiolane
  • Organic disulfide
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP1.87ALOGPS
logP1.75ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area240.36 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity176.04 m³·mol⁻¹ChemAxon
Polarizability71.43 ųChemAxon
Number of Rings5ChemAxon
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 Compound14187149
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]