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Record Information
Version2.0
Created at2022-04-29 02:29:35 UTC
Updated at2022-04-29 02:29:35 UTC
NP-MRD IDNP0081482
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Verbesinoside D
Description(1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-{[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}hexacyclo[12.9.0.0¹,²².0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]Tricos-13-ene-20-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-Verbesinoside D is found in Verbesina virginica. Based on a literature review very few articles have been published on (1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-{[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}hexacyclo[12.9.0.0¹,²².0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]Tricos-13-ene-20-carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
(1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-{[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}hexacyclo[12.9.0.0,.0,.0,.0,]tricos-13-ene-20-carboxylateGenerator
Chemical FormulaC58H84O21
Average Mass1117.2890 Da
Monoisotopic Mass1116.55051 Da
IUPAC Name(1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-{[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}hexacyclo[12.9.0.0^{1,22}.0^{2,11}.0^{5,10}.0^{15,20}]tricos-13-ene-20-carboxylic acid
Traditional Name(1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-{[(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}hexacyclo[12.9.0.0^{1,22}.0^{2,11}.0^{5,10}.0^{15,20}]tricos-13-ene-20-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C/C(=O)O[C@H]2C[C@@]3(C[C@H]4C[C@]44C(=CC[C@@H]5[C@@]6(C)CC[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]7OC[C@@H](O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)C(C)(C)[C@@H]6CC[C@@]45C)[C@@H]3CC2(C)C)C(O)=O)=CC(OC)=C1OC
InChI Identifier
InChI=1S/C58H84O21/c1-53(2)22-30-29-11-12-37-55(5)16-15-38(78-51-48(44(65)42(63)34(24-59)75-51)79-50-46(67)43(64)35(26-74-50)76-49-45(66)41(62)31(60)25-73-49)54(3,4)36(55)14-17-56(37,6)58(29)21-28(58)20-57(30,52(68)69)23-39(53)77-40(61)13-10-27-18-32(70-7)47(72-9)33(19-27)71-8/h10-11,13,18-19,28,30-31,34-39,41-46,48-51,59-60,62-67H,12,14-17,20-26H2,1-9H3,(H,68,69)/b13-10-/t28-,30-,31+,34+,35+,36-,37+,38-,39-,41-,42+,43-,44-,45+,46+,48+,49-,50-,51-,55-,56+,57+,58+/m0/s1
InChI KeyZKSYEGZSTCTSIS-SVOUWMIOSA-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
Verbesina virginicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Oligosaccharide
  • Fatty acyl glycoside
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Fatty acid ester
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP3.26ALOGPS
logP3.25ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.34ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area308.51 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity277.56 m³·mol⁻¹ChemAxon
Polarizability117.12 ųChemAxon
Number of Rings10ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162876626
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available