Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 12:49:50 UTC |
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Updated at | 2022-09-11 12:49:51 UTC |
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NP-MRD ID | NP0314635 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | [(1r,7s,9r,16s,21r,23s)-16-(acetyloxy)-3,14,25-trihydroxy-21-(2-methoxy-2-oxoethyl)-7,23-dimethyl-5,12,27-trioxo-8,22-dioxaheptacyclo[14.11.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-2,4(13),6(11),14,17(26),18,24-heptaen-9-yl]acetic acid |
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Description | Beta-Naphthocyclinone belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. [(1r,7s,9r,16s,21r,23s)-16-(acetyloxy)-3,14,25-trihydroxy-21-(2-methoxy-2-oxoethyl)-7,23-dimethyl-5,12,27-trioxo-8,22-dioxaheptacyclo[14.11.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-2,4(13),6(11),14,17(26),18,24-heptaen-9-yl]acetic acid is found in Streptomyces arenae. Based on a literature review very few articles have been published on beta-Naphthocyclinone. |
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Structure | COC(=O)C[C@H]1CC2=CC3=C(C(=O)[C@@H]4C[C@@]3(OC(C)=O)C3=C(O)C5=C(C(O)=C43)C(=O)C3=C(C[C@H](CC(O)=O)O[C@H]3C)C5=O)C(O)=C2[C@H](C)O1 InChI=1S/C35H32O14/c1-11-22-14(5-15(47-11)9-21(39)46-4)6-19-25(31(22)42)30(41)18-10-35(19,49-13(3)36)28-24(18)33(44)27-26(34(28)45)29(40)17-7-16(8-20(37)38)48-12(2)23(17)32(27)43/h6,11-12,15-16,18,42,44-45H,5,7-10H2,1-4H3,(H,37,38)/t11-,12-,15+,16+,18+,35-/m0/s1 |
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Synonyms | Value | Source |
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b-Naphthocyclinone | Generator | Β-naphthocyclinone | Generator |
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Chemical Formula | C35H32O14 |
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Average Mass | 676.6270 Da |
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Monoisotopic Mass | 676.17921 Da |
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IUPAC Name | 2-[(1R,7S,9R,16S,21R,23S)-16-(acetyloxy)-3,14,25-trihydroxy-21-(2-methoxy-2-oxoethyl)-7,23-dimethyl-5,12,27-trioxo-8,22-dioxaheptacyclo[14.11.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{17,26}.0^{19,24}]octacosa-2,4(13),6(11),14,17(26),18,24-heptaen-9-yl]acetic acid |
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Traditional Name | [(1R,7S,9R,16S,21R,23S)-16-(acetyloxy)-3,14,25-trihydroxy-21-(2-methoxy-2-oxoethyl)-7,23-dimethyl-5,12,27-trioxo-8,22-dioxaheptacyclo[14.11.1.0^{2,15}.0^{4,13}.0^{6,11}.0^{17,26}.0^{19,24}]octacosa-2,4(13),6(11),14,17(26),18,24-heptaen-9-yl]acetic acid |
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CAS Registry Number | Not Available |
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SMILES | COC(=O)C[C@H]1CC2=CC3=C(C(=O)[C@@H]4C[C@@]3(OC(C)=O)C3=C(O)C5=C(C(O)=C43)C(=O)C3=C(C[C@H](CC(O)=O)O[C@H]3C)C5=O)C(O)=C2[C@H](C)O1 |
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InChI Identifier | InChI=1S/C35H32O14/c1-11-22-14(5-15(47-11)9-21(39)46-4)6-19-25(31(22)42)30(41)18-10-35(19,49-13(3)36)28-24(18)33(44)27-26(34(28)45)29(40)17-7-16(8-20(37)38)48-12(2)23(17)32(27)43/h6,11-12,15-16,18,42,44-45H,5,7-10H2,1-4H3,(H,37,38)/t11-,12-,15+,16+,18+,35-/m0/s1 |
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InChI Key | ULOHVDHKDYSPRZ-KMXRVXEMSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Not Available |
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Sub Class | Not Available |
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Direct Parent | Lignans, neolignans and related compounds |
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Alternative Parents | |
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Substituents | - Neolignan skeleton
- Benzoisochromanequinone
- Naphthopyranone
- Dibenzocycloheptene
- Naphthopyran
- Naphthoquinone
- 2-benzopyran
- Tetralin
- Naphthalene
- Isochromane
- Benzopyran
- Tricarboxylic acid or derivatives
- Indane
- Aryl alkyl ketone
- Aryl ketone
- Quinone
- 1-hydroxy-4-unsubstituted benzenoid
- Pyranone
- Benzenoid
- Pyran
- Vinylogous acid
- Methyl ester
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Ether
- Dialkyl ether
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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