| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-29 02:29:26 UTC |
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| Updated at | 2022-04-29 02:29:26 UTC |
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| NP-MRD ID | NP0081480 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (+)-Verbesinoside B |
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| 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. |
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| Structure | 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=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 |
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| Synonyms | | Value | Source |
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| (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-carboxylate | Generator |
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| Chemical Formula | C51H74O17 |
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| Average Mass | 959.1360 Da |
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| Monoisotopic Mass | 958.49260 Da |
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| 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 |
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| 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 |
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| CAS Registry Number | Not Available |
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| 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 |
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| 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 |
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| InChI Key | SBNHOGAXBFZLIY-ICLYBJHESA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Triterpenoids |
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| Direct Parent | Triterpenoids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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