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Record Information
Version2.0
Created at2025-06-26 20:18:37 UTC
Updated at2025-06-29 06:32:50 UTC
NP-MRD IDNP0351167
Natural Product DOIhttps://doi.org/10.57994/4157
Secondary Accession NumbersNone
Natural Product Identification
Common Namekaempferol-3-O-α-rhamnoside
DescriptionAfzelin, also known as kaempferin or deacyl-SL0101, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Afzelin is an extremely weak basic (essentially neutral) compound (based on its pKa). kaempferol-3-O-α-rhamnoside was first documented in 2013 (PMID: 23626759). A glycosyloxyflavone that is kaempferol attached to a alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage (PMID: 24423008) (PMID: 24642906) (PMID: 40482233).
Structure
Thumb
Synonyms
ValueSource
KaempferinChEBI
Kaempferol 3-O-alpha-L-rhamnosideChEBI
Kaempferol 3-O-a-L-rhamnosideGenerator
Kaempferol 3-O-α-L-rhamnosideGenerator
Kaempferol-3-rhamnosideMeSH
Kaempferol-3-O-alpha-L-rhamnosideMeSH
Deacyl-SL0101MeSH
3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-onePhytoBank
3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-onePhytoBank
3-O-alpha-L-RhamnopyranosylkaempferolPhytoBank
3-O-α-L-RhamnopyranosylkaempferolPhytoBank
AfzelosidePhytoBank
Kaempferol 3-(6-deoxy-L-mannopyranoside)PhytoBank
Kaempferol 3-L-rhamnosidePhytoBank
Kaempferol 3-O-rhamnopyranosidePhytoBank
Kaempferol 3-O-rhamnosidePhytoBank
Kaempferol 3-O-alpha-L-rhamnopyranosidePhytoBank
Kaempferol 3-O-α-L-rhamnopyranosidePhytoBank
Kaempferol 3-rhamnosidePhytoBank
Kaempferol 3-alpha-L-rhamnopyranosidePhytoBank
Kaempferol 3-α-L-rhamnopyranosidePhytoBank
Kaempferol rhamnosidePhytoBank
Kaempferol-3-alpha-L-rhamnosePhytoBank
Kaempferol-3-α-L-rhamnosePhytoBank
Kaempherol 3-O-alpha-L-rhamnopyranosidePhytoBank
Kaempherol 3-O-α-L-rhamnopyranosidePhytoBank
Kaempherol 3-O-alpha-rhamnosidePhytoBank
Kaempherol 3-O-α-rhamnosidePhytoBank
Chemical FormulaC21H20O10
Average Mass432.3775 Da
Monoisotopic Mass432.10565 Da
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one
CAS Registry NumberNot Available
SMILES
C[C@@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1
InChI KeySOSLMHZOJATCCP-AEIZVZFYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)ististiqamah@gmail.comInstitut Teknologi BandungIsti Istiqamah2025-06-26View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)ististiqamah@gmail.comInstitut Teknologi BandungIsti Istiqamah2025-06-26View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)ististiqamah@gmail.comInstitut Teknologi BandungIsti Istiqamah2025-06-26View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)ististiqamah@gmail.comInstitut Teknologi BandungIsti Istiqamah2025-06-26View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pometia pinnata
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP1.48ALOGPS
logP1.21ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.75 m³·mol⁻¹ChemAxon
Polarizability41.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00005140
Chemspider IDNot Available
KEGG Compound IDC16911
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAfzelin
METLIN IDNot Available
PubChem Compound5316673
PDB IDNot Available
ChEBI ID80790
Good Scents IDNot Available
References
General References
  1. Shin SW, Jung E, Kim S, Kim JH, Kim EG, Lee J, Park D: Antagonizing effects and mechanisms of afzelin against UVB-induced cell damage. PLoS One. 2013 Apr 23;8(4):e61971. doi: 10.1371/journal.pone.0061971. Print 2013. [PubMed:23626759 ]
  2. Jiang Y, Lu Y, Zhang YY, Chen DF: Anti-complementary constituents of Houttuynia cordata and their targets in complement activation cascade. Nat Prod Res. 2014;28(6):407-10. doi: 10.1080/14786419.2013.869693. Epub 2014 Jan 15. [PubMed:24423008 ]
  3. Lee SY, So YJ, Shin MS, Cho JY, Lee J: Antibacterial effects of afzelin isolated from Cornus macrophylla on Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals. Molecules. 2014 Mar 17;19(3):3173-80. doi: 10.3390/molecules19033173. [PubMed:24642906 ]
  4. Istiqamah I, Herliana H, Fadilah A, Diniresna A, Fitriani R, Insanu M, Hermawati E, Happyana N: Secondary metabolites from Pometia pinnata leaves. Nat Prod Res. 2025 Jun 7:1-6. doi: 10.1080/14786419.2025.2514736. [PubMed:40482233 ]
  5. DOI: 10.1080/14786419.2025.2514736
  6. PMID: 40482233