Show more...
Record Information
Version2.0
Created at2022-04-28 05:09:43 UTC
Updated at2022-04-28 05:09:44 UTC
NP-MRD IDNP0060037
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-(3,4-Dihydroxyphenyl)-7-[[6-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-beta-D-glucopyranosyl]oxy]-5,6-dihydroxy-4H-1-benzopyran-4-one
DescriptionSpicoside a belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, spicoside a is considered to be a flavonoid. 2-(3,4-Dihydroxyphenyl)-7-[[6-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-beta-D-glucopyranosyl]oxy]-5,6-dihydroxy-4H-1-benzopyran-4-one is found in Halophila johnsonii and Veronica liwanensis. Based on a literature review very few articles have been published on Spicoside a.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H26O15
Average Mass626.5230 Da
Monoisotopic Mass626.12717 Da
IUPAC Name[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Name[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)O[C@@H](OC2=C(O)C(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C30H26O15/c31-14-4-1-12(7-16(14)33)2-6-23(36)42-11-22-26(38)28(40)29(41)30(45-22)44-21-10-20-24(27(39)25(21)37)18(35)9-19(43-20)13-3-5-15(32)17(34)8-13/h1-10,22,26,28-34,37-41H,11H2/b6-2+/t22-,26-,28+,29-,30-/m1/s1
InChI KeyUGSXKTPGBJVRGO-UFYYKPKHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Halophila johnsoniiLOTUS Database
Veronica liwanensisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • Flavone
  • 6-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acid ester
  • Pyranone
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Fatty acyl
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • 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
logP2.6ALOGPS
logP2.26ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.51ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area253.13 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity152.55 m³·mol⁻¹ChemAxon
Polarizability59.84 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 IDC00013690
Chemspider ID10186521
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21576580
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References