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Record Information
Version1.0
Created at2021-06-22 17:29:12 UTC
Updated at2021-06-22 17:29:13 UTC
NP-MRD IDNP0043920
Secondary Accession NumbersNone
Natural Product Identification
Common NameLonijaposide C
DescriptionLonijaposide C belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Lonijaposide C is found in Lonicera japonica. It was first documented in 2008 (PMID: 18321056). Based on a literature review very few articles have been published on Lonijaposide C.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H30NO12
Average Mass524.4980 Da
Monoisotopic Mass524.17625 Da
IUPAC Name3-carboxy-5-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]ethenyl]-1-(2-hydroxyethyl)pyridin-1-ium
Traditional Namelonijaposide C
CAS Registry NumberNot Available
SMILES
OCC[N+]1=CC(\C=C\[C@H]2[C@@H](C=C)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(O)=O)=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C24H29NO12/c1-2-14-15(4-3-12-7-13(21(31)32)9-25(8-12)5-6-26)16(22(33)34)11-35-23(14)37-24-20(30)19(29)18(28)17(10-27)36-24/h2-4,7-9,11,14-15,17-20,23-24,26-30H,1,5-6,10H2,(H-,31,32,33,34)/p+1/b4-3+/t14-,15+,17-,18-,19+,20-,23+,24+/m1/s1
InChI KeyDXFHNEGQVDLRDO-KBCYOOEFSA-O
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 125 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Deuterium oxide, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lonicera japonicaLinigton's dataset
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • Glycosyl compound
  • Secoiridoid-skeleton
  • O-glycosyl compound
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Oxane
  • Pyridine
  • Pyridinium
  • Heteroaromatic compound
  • Vinylogous ester
  • Vinylogous amide
  • Secondary alcohol
  • Alkanolamine
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Oxacycle
  • Acetal
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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-1.8ALOGPS
logP-5.5ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area207.32 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity126.37 m³·mol⁻¹ChemAxon
Polarizability52.01 ųChemAxon
Number of Rings3ChemAxon
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 IDC00039652
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24879107
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Song W, Li S, Wang S, Wu Y, Zi J, Gan M, Zhang Y, Liu M, Lin S, Yang Y, Shi J: Pyridinium alkaloid-coupled secoiridoids from the flower buds of Lonicera japonica. J Nat Prod. 2008 May;71(5):922-5. doi: 10.1021/np800040k. Epub 2008 Mar 6. [PubMed:18321056 ]