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Record Information
Version2.0
Created at2022-04-29 01:41:13 UTC
Updated at2022-04-29 01:41:13 UTC
NP-MRD IDNP0080688
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Lapathoside C
DescriptionLapathoside C belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. (+)-Lapathoside C is found in Polygonum lapathifolium , Polygonum cuspidatum and Polygonum sachalinensis. (+)-Lapathoside C was first documented in 2010 (PMID: 19698767). Based on a literature review a small amount of articles have been published on Lapathoside C (PMID: 31622095) (PMID: 23153813).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC40H42O18
Average Mass810.7580 Da
Monoisotopic Mass810.23711 Da
IUPAC Name[(2R,3R,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
Traditional Name[(2R,3R,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxolan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(\C=C\C(=O)OC[C@H]2O[C@H](O[C@]3(CO)O[C@H](COC(=O)\C=C\C4=CC=C(O)C=C4)[C@@H](O)[C@@H]3OC(=O)\C=C\C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)=C1
InChI Identifier
InChI=1S/C40H42O18/c1-52-28-18-24(6-14-27(28)44)9-16-32(46)53-19-29-34(48)36(50)37(51)39(55-29)58-40(21-41)38(56-33(47)17-8-23-4-12-26(43)13-5-23)35(49)30(57-40)20-54-31(45)15-7-22-2-10-25(42)11-3-22/h2-18,29-30,34-39,41-44,48-51H,19-21H2,1H3/b15-7+,16-9+,17-8+/t29-,30-,34-,35-,36+,37-,38+,39-,40+/m1/s1
InChI KeyWYNKDHNSWBVRAM-QVHYGTEESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Persicaria lapathifoliaPlant
Polygonum cuspidatumPlant
Polygonum sachalinensisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acid esters
Alternative Parents
Substituents
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • C-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • Tricarboxylic acid or derivatives
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Fatty acid ester
  • Alkyl aryl ether
  • Phenol
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Enoate ester
  • Oxolane
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Polyol
  • Ether
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • 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
logP2.69ALOGPS
logP3.5ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.03ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area277.66 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity199.88 m³·mol⁻¹ChemAxon
Polarizability81.12 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 IDC00046077
Chemspider ID9236941
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11061786
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kim D, Wang CY, Hu R, Lee JY, Luu TT, Park HJ, Lee SK: Antitumor Activity of Vanicoside B Isolated from Persicaria dissitiflora by Targeting CDK8 in Triple-Negative Breast Cancer Cells. J Nat Prod. 2019 Nov 22;82(11):3140-3149. doi: 10.1021/acs.jnatprod.9b00720. Epub 2019 Oct 17. [PubMed:31622095 ]
  2. Panda P, Appalashetti M, Natarajan M, Mary CP, Venkatraman SS, Judeh ZM: Synthesis and antiproliferative activity of helonioside A, 3',4',6'-tri-O-feruloylsucrose, lapathoside C and their analogs. Eur J Med Chem. 2012 Dec;58:418-30. doi: 10.1016/j.ejmech.2012.10.034. Epub 2012 Oct 27. [PubMed:23153813 ]
  3. Fan P, Terrier L, Hay AE, Marston A, Hostettmann K: Antioxidant and enzyme inhibition activities and chemical profiles of Polygonum sachalinensis F.Schmidt ex Maxim (Polygonaceae). Fitoterapia. 2010 Mar;81(2):124-31. doi: 10.1016/j.fitote.2009.08.019. Epub 2009 Aug 19. [PubMed:19698767 ]