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Record Information
Version2.0
Created at2022-04-29 02:29:26 UTC
Updated at2022-04-29 02:29:26 UTC
NP-MRD IDNP0081480
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Verbesinoside B
Description(1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-(3,4,5-trimethoxybenzoyloxy)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 B 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)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-(3,4,5-trimethoxybenzoyloxy)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)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-(3,4,5-trimethoxybenzoyloxy)hexacyclo[12.9.0.0,.0,.0,.0,]tricos-13-ene-20-carboxylateGenerator
Chemical FormulaC51H74O17
Average Mass959.1360 Da
Monoisotopic Mass958.49260 Da
IUPAC Name(1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-(3,4,5-trimethoxybenzoyloxy)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)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2,6,6,10,17,17-hexamethyl-18-(3,4,5-trimethoxybenzoyloxy)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(=CC(OC)=C1OC)C(=O)O[C@H]1C[C@@]2(C[C@H]3C[C@]33C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6OC[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2CC1(C)C)C(O)=O
InChI Identifier
InChI=1S/C51H74O17/c1-46(2)20-27-26-10-11-33-48(5)14-13-34(67-44-41(38(56)37(55)31(22-52)65-44)68-43-39(57)36(54)28(53)23-64-43)47(3,4)32(48)12-15-49(33,6)51(26)19-25(51)18-50(27,45(59)60)21-35(46)66-42(58)24-16-29(61-7)40(63-9)30(17-24)62-8/h10,16-17,25,27-28,31-39,41,43-44,52-57H,11-15,18-23H2,1-9H3,(H,59,60)/t25-,27-,28+,31+,32-,33+,34-,35-,36-,37+,38-,39+,41+,43-,44-,48-,49+,50+,51+/m0/s1
InChI KeySBNHOGAXBFZLIY-ICLYBJHESA-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
  • Hydrolyzable tannin
  • Tannin
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Gallic acid or derivatives
  • P-methoxybenzoic acid or derivatives
  • O-glycosyl compound
  • M-methoxybenzoic acid or derivatives
  • Glycosyl compound
  • Disaccharide
  • Benzoate ester
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • 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
logP3.86ALOGPS
logP3.85ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area249.59 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity241.36 m³·mol⁻¹ChemAxon
Polarizability104.28 ųChemAxon
Number of Rings9ChemAxon
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 Compound162949733
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available