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Record Information
Version2.0
Created at2023-02-08 08:01:57 UTC
Updated at2024-09-03 04:15:57 UTC
NP-MRD IDNP0331506
Natural Product DOIhttps://doi.org/10.57994/0466
Secondary Accession NumbersNone
Natural Product Identification
Common NameArteannumonoside E
DescriptionArteannumonoside E belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Arteannumonoside E was first documented in 2023 (PMID: 36740572). Based on a literature review very few articles have been published on Arteannumonoside E.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H36O11
Average Mass464.5080 Da
Monoisotopic Mass464.22576 Da
IUPAC Name(2R,3S,4S,5R,6R)-2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[(2S)-3-hydroxy-3-methyl-2-[(1E)-3-methylbuta-1,3-dien-1-yl]butoxy]oxane-3,4,5-triol
Traditional Name(2R,3S,4S,5R,6R)-2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[(2S)-3-hydroxy-3-methyl-2-[(1E)-3-methylbuta-1,3-dien-1-yl]butoxy]oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
[H][C@@](CO[C@@H]1O[C@H](COC2OCC(O)(CO)C2O)[C@@H](O)[C@H](O)[C@H]1O)(\C=C\C(C)=C)C(C)(C)O
InChI Identifier
InChI=1S/C21H36O11/c1-11(2)5-6-12(20(3,4)27)7-29-18-16(25)15(24)14(23)13(32-18)8-30-19-17(26)21(28,9-22)10-31-19/h5-6,12-19,22-28H,1,7-10H2,2-4H3/b6-5+/t12-,13+,14+,15-,16+,17?,18+,19?,21?/m0/s1
InChI KeyPHYXAZDYTODQOA-IHPJTZAYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
NOESY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, D2O, experimental)qiguo_wu@163.comNot AvailableNot Available2024-05-11View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, D2O, experimental)qiguo_wu@163.comNot AvailableNot Available2024-05-11View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, D2O, experimental)qiguo_wu@163.comNot AvailableNot Available2024-05-11View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, D2O, experimental)qiguo_wu@163.comNot AvailableNot Available2024-05-11View Spectrum
1D_DEPT NMR13C NMR Spectrum (1D, 101 MHz, D2O, experimental)qiguo_wu@163.comNot AvailableNot Available2024-05-11View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, experimental)qiguo_wu@163.comNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)qiguo_wu@163.comNot AvailableNot Available2024-05-11View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500.11, CD3OD, simulated)Not AvailableNot AvailableNot Available2024-05-11View Spectrum
Species
Species of Origin
Species NameSourceReference
annua
      Not Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. These are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Glycerolipid
  • Oxane
  • Monosaccharide
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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
logP-2.1ChemAxon
pKa (Strongest Acidic)11.7ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area178.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity111.22 m³·mol⁻¹ChemAxon
Polarizability47.11 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wu QG, Huang LY, Fan MH, Chou GX, Wang YL: Anti-Inflammatory Activities of Monoterpene and Sesquiterpene Glycosides from the Aqueous Extract of Artemisia annua L. Chem Biodivers. 2023 Mar;20(3):e202201237. doi: 10.1002/cbdv.202201237. Epub 2023 Feb 21. [PubMed:36740572 ]