| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-29 02:29:35 UTC |
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| Updated at | 2022-04-29 02:29:35 UTC |
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| NP-MRD ID | NP0081482 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (+)-Verbesinoside D |
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| 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. |
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| Structure | 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=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 |
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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)-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-carboxylate | Generator |
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| Chemical Formula | C58H84O21 |
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| Average Mass | 1117.2890 Da |
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| Monoisotopic Mass | 1116.55051 Da |
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| 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 |
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| 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 |
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| CAS Registry Number | Not Available |
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| 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 |
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| 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 |
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| InChI Key | ZKSYEGZSTCTSIS-SVOUWMIOSA-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 |
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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
- 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
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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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