| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 15:25:13 UTC |
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| Updated at | 2022-09-12 15:25:14 UTC |
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| NP-MRD ID | NP0330252 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (2s,3r,4r,6s)-6-{[(2r,3s,6s)-6-{[(1s,4as,12ar)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,12-dihydrotetracen-1-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl (2z,4r)-2,4-dimethylhept-2-enoate |
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| Description | Dutomycin belongs to the class of organic compounds known as anthraquinone glycosides. These are organic compounds containing an anthraquinone moiety glycosidically bound to a carbohydrate moiety. (2s,3r,4r,6s)-6-{[(2r,3s,6s)-6-{[(1s,4as,12ar)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,12-dihydrotetracen-1-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl (2z,4r)-2,4-dimethylhept-2-enoate was first documented in 2016 (PMID: 27195476). Based on a literature review a small amount of articles have been published on Dutomycin (PMID: 35630823) (PMID: 34824375) (PMID: 33517652). |
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| Structure | CCC[C@@H](C)\C=C(\C)C(=O)O[C@@H]1[C@H](C)O[C@H](C[C@@]1(C)O)O[C@H]1CC[C@H](O[C@@H]2C(=O)C(C(C)=O)=C(O)[C@@]3(O)C(=O)C4=C(O)C5=C(C(C)=C4C[C@@]23O)C(=O)C(OC)=CC5=O)O[C@@H]1C InChI=1S/C44H54O17/c1-10-11-18(2)14-19(3)41(52)61-39-23(7)58-29(17-42(39,8)53)59-26-12-13-28(57-22(26)6)60-40-36(49)31(21(5)45)37(50)44(55)38(51)32-24(16-43(40,44)54)20(4)30-33(35(32)48)25(46)15-27(56-9)34(30)47/h14-15,18,22-23,26,28-29,39-40,48,50,53-55H,10-13,16-17H2,1-9H3/b19-14-/t18-,22-,23+,26+,28+,29+,39-,40-,42-,43-,44-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C44H54O17 |
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| Average Mass | 854.8990 Da |
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| Monoisotopic Mass | 854.33610 Da |
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| IUPAC Name | (2S,3R,4R,6S)-6-{[(2R,3S,6S)-6-{[(1S,4aS,12aR)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,2,4a,5,7,10,12,12a-octahydrotetracen-1-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl (2Z,4R)-2,4-dimethylhept-2-enoate |
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| Traditional Name | (2S,3R,4R,6S)-6-{[(2R,3S,6S)-6-{[(1S,4aS,12aR)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,12-dihydrotetracen-1-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl (2Z,4R)-2,4-dimethylhept-2-enoate |
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| CAS Registry Number | Not Available |
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| SMILES | CCC[C@@H](C)\C=C(\C)C(=O)O[C@@H]1[C@H](C)O[C@H](C[C@@]1(C)O)O[C@H]1CC[C@H](O[C@@H]2C(=O)C(C(C)=O)=C(O)[C@@]3(O)C(=O)C4=C(O)C5=C(C(C)=C4C[C@@]23O)C(=O)C(OC)=CC5=O)O[C@@H]1C |
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| InChI Identifier | InChI=1S/C44H54O17/c1-10-11-18(2)14-19(3)41(52)61-39-23(7)58-29(17-42(39,8)53)59-26-12-13-28(57-22(26)6)60-40-36(49)31(21(5)45)37(50)44(55)38(51)32-24(16-43(40,44)54)20(4)30-33(35(32)48)25(46)15-27(56-9)34(30)47/h14-15,18,22-23,26,28-29,39-40,48,50,53-55H,10-13,16-17H2,1-9H3/b19-14-/t18-,22-,23+,26+,28+,29+,39-,40-,42-,43-,44-/m1/s1 |
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| InChI Key | ZYPYHMZLLIDAAL-WNMWLNICSA-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 | Not Available |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as anthraquinone glycosides. These are organic compounds containing an anthraquinone moiety glycosidically bound to a carbohydrate moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Anthracenes |
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| Sub Class | Anthraquinones |
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| Direct Parent | Anthraquinone glycosides |
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| Alternative Parents | |
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| Substituents | - Anthraquinone glycoside
- O-glycosyl compound
- Disaccharide
- Glycosyl compound
- Naphthalene
- Tetralin
- Quinone
- Aryl alkyl ketone
- Aryl ketone
- Cyclohexenone
- Fatty acid ester
- Fatty acyl
- Oxane
- Vinylogous acid
- Tertiary alcohol
- Vinylogous ester
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Cyclic ketone
- Ketone
- Carboxylic acid ester
- Acetal
- Carboxylic acid derivative
- Enol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Monocarboxylic acid or derivatives
- Organic oxide
- Hydrocarbon derivative
- Aldehyde
- Organic oxygen compound
- Carbonyl group
- Alcohol
- 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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