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Record Information
Version2.0
Created at2022-09-08 21:05:27 UTC
Updated at2022-09-08 21:05:27 UTC
NP-MRD IDNP0273897
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
DescriptionSwertisin 2''-o-arabinoside belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, swertisin 2''-O-arabinoside is considered to be a flavonoid. 6-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one is found in Achillea fragrantissima. Based on a literature review very few articles have been published on Swertisin 2''-o-arabinoside.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H30O14
Average Mass578.5230 Da
Monoisotopic Mass578.16356 Da
IUPAC Name6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
Traditional Name6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
CAS Registry NumberNot Available
SMILES
COC1=C([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C27H30O14/c1-37-15-7-16-18(12(30)6-14(39-16)10-2-4-11(29)5-3-10)22(34)19(15)25-26(23(35)21(33)17(8-28)40-25)41-27-24(36)20(32)13(31)9-38-27/h2-7,13,17,20-21,23-29,31-36H,8-9H2,1H3/t13-,17+,20-,21+,23-,24+,25-,26+,27-/m0/s1
InChI KeyITURUJYQEZMYRK-ORNBPAKCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea fragrantissimaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Disaccharide
  • Chromone
  • C-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Ether
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP-1ChemAxon
pKa (Strongest Acidic)6.93ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity136.97 m³·mol⁻¹ChemAxon
Polarizability56.34 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 IDC00006225
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101422754
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]