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Record Information
Version2.0
Created at2022-09-11 19:52:30 UTC
Updated at2022-09-11 19:52:30 UTC
NP-MRD IDNP0319041
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxychromen-4-one
Description2''-O-D-Apiofuranosylabrusin belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. 8-[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxychromen-4-one is found in Abrus precatorius. Based on a literature review very few articles have been published on 2''-O-D-Apiofuranosylabrusin.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H32O15
Average Mass608.5490 Da
Monoisotopic Mass608.17412 Da
IUPAC Name8-[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-4H-chromen-4-one
Traditional Name8-[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxychromen-4-one
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2OC[C@](O)(CO)[C@H]2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C28H32O15/c1-38-22-17(21-16(19(34)24(22)39-2)13(32)7-14(41-21)11-3-5-12(31)6-4-11)23-25(20(35)18(33)15(8-29)42-23)43-27-26(36)28(37,9-30)10-40-27/h3-7,15,18,20,23,25-27,29-31,33-37H,8-10H2,1-2H3/t15-,18-,20+,23+,25-,26+,27+,28-/m1/s1
InChI KeyMFAXEOJBTQFANX-IPSJCSPLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abrus precatoriusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • C-glycosyl compound
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxolane
  • Tertiary alcohol
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Dialkyl ether
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • 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-1.3ChemAxon
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.29 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity143.65 m³·mol⁻¹ChemAxon
Polarizability58.65 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 Compound101591983
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]