Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 19:24:49 UTC |
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Updated at | 2022-04-28 19:24:49 UTC |
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NP-MRD ID | NP0074258 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Hirtellin B |
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Description | (10R,11R,12R,13S,15S)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]Tricosa-1(23),2,4,6,19,21-hexaen-12-yl 3,4,5-trihydroxy-2-{[(1S,3R,20S,21S,22S)-8,9,10,13,14,27,28,29,32,33,34-undecahydroxy-5,18,24,37-tetraoxo-21-(3,4,5-trihydroxybenzoyloxy)-2,4,19,23,38-pentaoxaheptacyclo[20.17.0.0³,²⁰.0⁶,¹¹.0¹²,¹⁷.0²⁵,³⁰.0³¹,³⁶]Nonatriaconta-6,8,10,12,14,16,25,27,29,31,33,35-dodecaen-15-yl]oxy}benzoate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Hirtellin B is found in Reaumuria hirtella. It was first documented in 2022 (PMID: 35489815). Based on a literature review a significant number of articles have been published on (10R,11R,12R,13S,15S)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]Tricosa-1(23),2,4,6,19,21-hexaen-12-yl 3,4,5-trihydroxy-2-{[(1S,3R,20S,21S,22S)-8,9,10,13,14,27,28,29,32,33,34-undecahydroxy-5,18,24,37-tetraoxo-21-(3,4,5-trihydroxybenzoyloxy)-2,4,19,23,38-pentaoxaheptacyclo[20.17.0.0³,²⁰.0⁶,¹¹.0¹²,¹⁷.0²⁵,³⁰.0³¹,³⁶]Nonatriaconta-6,8,10,12,14,16,25,27,29,31,33,35-dodecaen-15-yl]oxy}benzoate (PMID: 35489814) (PMID: 35489813) (PMID: 35489812) (PMID: 35489811). |
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Structure | OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@H]2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@H]2[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1OC(=O)C1=C(OC2=C(O)C(O)=C3C(=C2)C(=O)O[C@@H]2[C@H](O[C@H]4COC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(C=C(O)C(O)=C5O)C(=O)O[C@@H]4[C@@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)OC(=O)C2=C3C(O)=C(O)C(O)=C2)C(O)=C(O)C(O)=C1 InChI=1S/C82H56O52/c83-26-1-16(2-27(84)47(26)95)71(112)129-67-65-39(14-122-74(115)19-7-32(89)50(98)57(105)41(19)43-21(76(117)127-65)9-34(91)52(100)59(43)107)125-81(133-73(114)18-5-30(87)49(97)31(88)6-18)69(67)132-80(121)25-12-37(94)55(103)63(111)64(25)124-38-13-24-46(62(110)56(38)104)45-23(11-36(93)54(102)61(45)109)79(120)134-82-70(131-78(24)119)68(130-72(113)17-3-28(85)48(96)29(86)4-17)66-40(126-82)15-123-75(116)20-8-33(90)51(99)58(106)42(20)44-22(77(118)128-66)10-35(92)53(101)60(44)108/h1-13,39-40,65-70,81-111H,14-15H2/t39-,40-,65+,66-,67+,68-,69+,70-,81-,82+/m0/s1 |
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Synonyms | Value | Source |
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(10R,11R,12R,13S,15S)-3,4,5,21,22,23-Hexahydroxy-8,18-dioxo-11,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0,.0,]tricosa-1(23),2,4,6,19,21-hexaen-12-yl 3,4,5-trihydroxy-2-{[(1S,3R,20S,21S,22S)-8,9,10,13,14,27,28,29,32,33,34-undecahydroxy-5,18,24,37-tetraoxo-21-(3,4,5-trihydroxybenzoyloxy)-2,4,19,23,38-pentaoxaheptacyclo[20.17.0.0,.0,.0,.0,.0,]nonatriaconta-6,8,10,12,14,16,25,27,29,31,33,35-dodecaen-15-yl]oxy}benzoic acid | Generator |
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Chemical Formula | C82H56O52 |
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Average Mass | 1873.2980 Da |
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Monoisotopic Mass | 1872.17376 Da |
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IUPAC Name | (10R,11R,12R,13S,15S)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-12-yl 3,4,5-trihydroxy-2-{[(1S,3R,20S,21S,22S)-8,9,10,13,14,27,28,29,32,33,34-undecahydroxy-5,18,24,37-tetraoxo-21-(3,4,5-trihydroxybenzoyloxy)-2,4,19,23,38-pentaoxaheptacyclo[20.17.0.0^{3,20}.0^{6,11}.0^{12,17}.0^{25,30}.0^{31,36}]nonatriaconta-6(11),7,9,12,14,16,25(30),26,28,31(36),32,34-dodecaen-15-yl]oxy}benzoate |
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Traditional Name | (10R,11R,12R,13S,15S)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-12-yl 3,4,5-trihydroxy-2-{[(1S,3R,20S,21S,22S)-8,9,10,13,14,27,28,29,32,33,34-undecahydroxy-5,18,24,37-tetraoxo-21-(3,4,5-trihydroxybenzoyloxy)-2,4,19,23,38-pentaoxaheptacyclo[20.17.0.0^{3,20}.0^{6,11}.0^{12,17}.0^{25,30}.0^{31,36}]nonatriaconta-6(11),7,9,12,14,16,25(30),26,28,31(36),32,34-dodecaen-15-yl]oxy}benzoate |
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CAS Registry Number | Not Available |
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SMILES | OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@H]2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@H]2[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1OC(=O)C1=C(OC2=C(O)C(O)=C3C(=C2)C(=O)O[C@@H]2[C@H](O[C@H]4COC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(C=C(O)C(O)=C5O)C(=O)O[C@@H]4[C@@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)OC(=O)C2=C3C(O)=C(O)C(O)=C2)C(O)=C(O)C(O)=C1 |
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InChI Identifier | InChI=1S/C82H56O52/c83-26-1-16(2-27(84)47(26)95)71(112)129-67-65-39(14-122-74(115)19-7-32(89)50(98)57(105)41(19)43-21(76(117)127-65)9-34(91)52(100)59(43)107)125-81(133-73(114)18-5-30(87)49(97)31(88)6-18)69(67)132-80(121)25-12-37(94)55(103)63(111)64(25)124-38-13-24-46(62(110)56(38)104)45-23(11-36(93)54(102)61(45)109)79(120)134-82-70(131-78(24)119)68(130-72(113)17-3-28(85)48(96)29(86)4-17)66-40(126-82)15-123-75(116)20-8-33(90)51(99)58(106)42(20)44-22(77(118)128-66)10-35(92)53(101)60(44)108/h1-13,39-40,65-70,81-111H,14-15H2/t39-,40-,65+,66-,67+,68-,69+,70-,81-,82+/m0/s1 |
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InChI Key | FLPCODRBPBQITI-UIVJKMCMSA-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 hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Tannins |
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Sub Class | Hydrolyzable tannins |
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Direct Parent | Hydrolyzable tannins |
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Alternative Parents | |
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Substituents | - Hydrolyzable tannin
- Galloyl ester
- Gallic acid or derivatives
- P-hydroxybenzoic acid alkyl ester
- M-hydroxybenzoic acid ester
- P-hydroxybenzoic acid ester
- Dihydroxybenzoic acid
- Diaryl ether
- Benzoate ester
- Pyrogallol derivative
- Benzoic acid or derivatives
- Benzenetriol
- Phenoxy compound
- Phenol ether
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Oxane
- Monosaccharide
- Monocyclic benzene moiety
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Ether
- Carboxylic acid derivative
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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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