Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:48 UTC |
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HMDB ID | HMDB0014964 |
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Secondary Accession Numbers | - HMDB0030468
- HMDB14964
- HMDB30468
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Metabolite Identification |
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Common Name | Natamycin |
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Description | Natamycin is only found in individuals that have used or taken this drug. It is an amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. [PubChem]Like other polyene antibiotics, Natamycin inhibits fungal growth by binding to sterols. Specifically, Natamycin binds to ergosterol in the plasma membrane, preventing ergosterol-dependent fusion of vacuoles, as well as membrane fusion and fission. This differs from the mechanism of most other polyene antibiotics, which tend to work by altering fungal membrane permeability instead. |
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Structure | C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32?,33-/m1/s1 |
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Synonyms | Value | Source |
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Pimaricin | Kegg | Natacyn | Kegg | PMR | KEGG | a 5283 | HMDB | Antibiotic a 5283 | HMDB | Antibiotic a-5283 | HMDB | CL 12625 | HMDB | Delvocid | HMDB | Delvolan | HMDB | Delvopos | HMDB | e235 | HMDB | Mycophyt | HMDB | Myprozine | HMDB, MeSH | Natafucin | HMDB | Pimafucin | HMDB, MeSH | Pimafugin | HMDB | Pimaricin (JP15) | HMDB | Pimaricine | HMDB | Synogil | HMDB | Tennecetin | HMDB, MeSH | Tymasil | HMDB |
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Chemical Formula | C33H47NO13 |
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Average Molecular Weight | 665.7252 |
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Monoisotopic Molecular Weight | 665.304740595 |
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IUPAC Name | (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0⁵,⁷]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid |
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Traditional Name | natamycin |
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CAS Registry Number | 7681-93-8 |
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SMILES | C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O |
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InChI Identifier | InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32?,33-/m1/s1 |
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InChI Key | NCXMLFZGDNKEPB-BQGNJOPGSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Aminoglycosides |
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Alternative Parents | |
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Substituents | - Aminoglycoside core
- Macrolide
- Hexose monosaccharide
- O-glycosyl compound
- Glycosyl compound
- Beta-hydroxy acid
- Hydroxy acid
- Monosaccharide
- Dicarboxylic acid or derivatives
- Oxane
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Hemiacetal
- Secondary alcohol
- Carboxylic acid ester
- Amino acid
- Amino acid or derivatives
- 1,2-aminoalcohol
- Lactone
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Carboxylic acid
- Dialkyl ether
- Organoheterocyclic compound
- Oxirane
- Ether
- Polyol
- Alcohol
- Organic nitrogen compound
- Amine
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Carbonyl group
- Organonitrogen compound
- Primary aliphatic amine
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (Non-derivatized) - 70eV, Positive | splash10-002b-9200015000-f595a5ec647350aa5e44 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_1_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_11) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_12) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_13) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_14) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_15) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_16) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Natamycin GC-MS (TMS_2_17) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 10V, Positive-QTOF | splash10-0ul1-0000159000-db7c73a2c6e943055873 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 20V, Positive-QTOF | splash10-0udi-0300292000-e96b0296247cf041eb27 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 40V, Positive-QTOF | splash10-0f6t-0509350000-4c2c7b4ac6bdbd8f7641 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 10V, Negative-QTOF | splash10-0w9a-2000139000-12a04d582d7eb949cc7f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 20V, Negative-QTOF | splash10-0fr2-0000192000-dbfe316890501907db18 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 40V, Negative-QTOF | splash10-0aor-9202420000-e05573710a8f58a421d2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 10V, Positive-QTOF | splash10-0uxs-0000059000-3e978a72825660654a87 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 20V, Positive-QTOF | splash10-0udi-0000094000-2dfd35d7e9ce10554843 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 40V, Positive-QTOF | splash10-0fl1-8500193000-9281f959f7d6a0dfa98b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 10V, Negative-QTOF | splash10-0imi-0200219000-3319c9ecec161550e327 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 20V, Negative-QTOF | splash10-0ik9-2000395000-60d0b7e3401384f6ddb3 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Natamycin 40V, Negative-QTOF | splash10-0udi-1000390000-a1a7a8f92824688e8cf0 | 2021-10-11 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
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