| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-05 07:41:10 UTC |
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| Updated at | 2022-09-05 07:41:11 UTC |
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| NP-MRD ID | NP0210034 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-9-[(2r,3r)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]-2h,3h-naphtho[2,3-b]pyran-4-one |
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| Description | Chaetochromin A belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Chaetochromin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-9-[(2r,3r)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]-2h,3h-naphtho[2,3-b]pyran-4-one is found in Collariella gracilis and Floropilus chiversii. (2s,3s)-5,6,8-trihydroxy-2,3-dimethyl-9-[(2r,3r)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]-2h,3h-naphtho[2,3-b]pyran-4-one was first documented in 2007 (PMID: 18052326). Based on a literature review very few articles have been published on chaetochromin A (PMID: 24900483). |
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| Structure | C[C@H]1OC2=CC3=C(C(O)=CC(O)=C3C(O)=C2C(=O)[C@@H]1C)C1=C(O)C=C(O)C2=C(O)C3=C(O[C@@H](C)[C@H](C)C3=O)C=C12 InChI=1S/C30H26O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-12,31-34,37-38H,1-4H3/t9-,10+,11-,12+ |
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| Synonyms | | Value | Source |
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| Chaetochromin D | MeSH | | Chaetochromin b | MeSH | | Chaetochromin, stereoisomer | MeSH | | Chaetochromin | MeSH |
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| Chemical Formula | C30H26O10 |
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| Average Mass | 546.5280 Da |
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| Monoisotopic Mass | 546.15260 Da |
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| IUPAC Name | (2S,3S)-5,6,8-trihydroxy-2,3-dimethyl-9-[(2R,3R)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2H,3H,4H-naphtho[2,3-b]pyran-9-yl]-2H,3H,4H-naphtho[2,3-b]pyran-4-one |
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| Traditional Name | (2S,3S)-5,6,8-trihydroxy-2,3-dimethyl-9-[(2R,3R)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2H,3H-naphtho[2,3-b]pyran-9-yl]-2H,3H-naphtho[2,3-b]pyran-4-one |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H]1OC2=CC3=C(C(O)=CC(O)=C3C(O)=C2C(=O)[C@@H]1C)C1=C(O)C=C(O)C2=C(O)C3=C(O[C@@H](C)[C@H](C)C3=O)C=C12 |
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| InChI Identifier | InChI=1S/C30H26O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-12,31-34,37-38H,1-4H3/t9-,10+,11-,12+ |
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| InChI Key | RHNVLFNWDGWACV-BKUVIOGVSA-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 naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Naphthopyrans |
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| Sub Class | Naphthopyranones |
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| Direct Parent | Naphthopyranones |
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| Alternative Parents | |
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| Substituents | - Naphthopyranone
- Benzochromone
- Biphenol
- 2-naphthol
- 1-naphthol
- Chromone
- Naphthalene
- Chromane
- Benzopyran
- 1-benzopyran
- Aryl ketone
- Aryl alkyl ketone
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- Pyran
- Benzenoid
- Vinylogous acid
- Ketone
- Oxacycle
- Polyol
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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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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