Record Information |
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Version | 1.0 |
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Created at | 2022-09-06 03:03:29 UTC |
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Updated at | 2022-09-06 03:03:29 UTC |
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NP-MRD ID | NP0224587 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | [(1r,3s)-8-[(1r,3s)-3-(carboxymethyl)-1-methyl-5,6,9,10-tetraoxo-1h,3h,4h-naphtho[2,3-c]pyran-8-yl]-5,6,9,10-tetrahydroxy-1-methyl-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetic acid |
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Description | Actinorhodin belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. [(1r,3s)-8-[(1r,3s)-3-(carboxymethyl)-1-methyl-5,6,9,10-tetraoxo-1h,3h,4h-naphtho[2,3-c]pyran-8-yl]-5,6,9,10-tetrahydroxy-1-methyl-1h,3h,4h-naphtho[2,3-c]pyran-3-yl]acetic acid is found in Streptomyces albidoflavus and Streptomyces coelicolor. It was first documented in 2022 (PMID: 35898901). Based on a literature review a significant number of articles have been published on Actinorhodin (PMID: 35487928) (PMID: 35625182) (PMID: 35557750) (PMID: 35467418). |
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Structure | C[C@H]1O[C@H](CC(O)=O)CC2=C1C(O)=C1C(O)=C(C=C(O)C1=C2O)C1=CC(=O)C2=C(C1=O)C(=O)C1=C(C[C@@H](CC(O)=O)O[C@@H]1C)C2=O InChI=1S/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,33,39,41,43H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1 |
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Synonyms | Value | Source |
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Actinorhodine | MeSH |
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Chemical Formula | C32H26O14 |
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Average Mass | 634.5460 Da |
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Monoisotopic Mass | 634.13226 Da |
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IUPAC Name | 2-[(1R,3S)-8-[(1R,3S)-3-(carboxymethyl)-1-methyl-5,6,9,10-tetraoxo-1H,3H,4H,5H,6H,9H,10H-naphtho[2,3-c]pyran-8-yl]-5,6,9,10-tetrahydroxy-1-methyl-1H,3H,4H-naphtho[2,3-c]pyran-3-yl]acetic acid |
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Traditional Name | [(1R,3S)-8-[(1R,3S)-3-(carboxymethyl)-1-methyl-5,6,9,10-tetraoxo-1H,3H,4H-naphtho[2,3-c]pyran-8-yl]-5,6,9,10-tetrahydroxy-1-methyl-1H,3H,4H-naphtho[2,3-c]pyran-3-yl]acetic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@H]1O[C@H](CC(O)=O)CC2=C1C(O)=C1C(O)=C(C=C(O)C1=C2O)C1=CC(=O)C2=C(C1=O)C(=O)C1=C(C[C@@H](CC(O)=O)O[C@@H]1C)C2=O |
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InChI Identifier | InChI=1S/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,33,39,41,43H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1 |
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InChI Key | MGFJRQUGYNFFDQ-WYUUTHIRSA-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 isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Isochromanequinones |
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Sub Class | Not Available |
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Direct Parent | Isochromanequinones |
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Alternative Parents | |
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Substituents | - Isochromanequinone
- Naphthopyranone
- Naphthopyran
- 1-naphthol
- 2-benzopyran
- Naphthalene
- Isochromane
- Benzopyran
- Hydroquinone
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Benzenoid
- Pyran
- Dicarboxylic acid or derivatives
- 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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