Record Information |
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Version | 1.0 |
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Created at | 2022-09-05 17:18:38 UTC |
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Updated at | 2022-09-05 17:18:38 UTC |
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NP-MRD ID | NP0217086 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (s)-{[(2s,3s,4s)-2-amino-1,4-dihydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid |
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Description | Nikkomycin X belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. (s)-{[(2s,3s,4s)-2-amino-1,4-dihydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutylidene]amino}[(2r,3s,4r,5r)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid is found in Streptomyces cacaoi and Streptomyces tendae. It was first documented in 2009 (PMID: 19930628). Based on a literature review a significant number of articles have been published on Nikkomycin X (PMID: 26562995) (PMID: 24751325) (PMID: 21292022) (PMID: 20096125). |
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Structure | C[C@@H]([C@H](N)C(O)=N[C@@H]([C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(C=O)N=C1O)C(O)=O)[C@H](O)C1=CC=C(O)C=N1 InChI=1S/C20H25N5O10/c1-7(13(28)10-3-2-9(27)4-22-10)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-8(6-26)23-20(25)34/h2-7,11-16,18,27-30H,21H2,1H3,(H,23,34)(H,24,31)(H,32,33)/t7-,11-,12-,13-,14-,15+,16+,18+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H25N5O10 |
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Average Mass | 495.4450 Da |
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Monoisotopic Mass | 495.16014 Da |
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IUPAC Name | (2S)-2-{[(2S,3S,4S)-2-amino-1,4-dihydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutylidene]amino}-2-[(2R,3S,4R,5R)-5-(4-formyl-2-hydroxy-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid |
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Traditional Name | (S)-{[(2S,3S,4S)-2-amino-1,4-dihydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutylidene]amino}[(2R,3S,4R,5R)-5-(4-formyl-2-hydroxyimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]([C@H](N)C(O)=N[C@@H]([C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=C(C=O)N=C1O)C(O)=O)[C@H](O)C1=CC=C(O)C=N1 |
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InChI Identifier | InChI=1S/C20H25N5O10/c1-7(13(28)10-3-2-9(27)4-22-10)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-8(6-26)23-20(25)34/h2-7,11-16,18,27-30H,21H2,1H3,(H,23,34)(H,24,31)(H,32,33)/t7-,11-,12-,13-,14-,15+,16+,18+/m0/s1 |
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InChI Key | AYXHZRVSIUJLAE-VHDFTHOZSA-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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Dipeptides |
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Alternative Parents | |
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Substituents | - Alpha-dipeptide
- N-acyl-alpha amino acid or derivatives
- N-acyl-l-alpha-amino acid
- N-acyl-alpha-amino acid
- Alpha-amino acid amide
- Glycosyl compound
- N-glycosyl compound
- Alpha-amino acid or derivatives
- Imidazolyl carboxylic acid derivative
- Imidazole-4-carbonyl group
- Aralkylamine
- Aryl-aldehyde
- Hydroxypyridine
- N-substituted imidazole
- Fatty acyl
- Fatty amide
- Pyridine
- N-acyl-amine
- 1,3-aminoalcohol
- Heteroaromatic compound
- Azole
- Imidazole
- Oxolane
- Vinylogous amide
- Carboxamide group
- Amino acid or derivatives
- Amino acid
- Urea
- Secondary alcohol
- Secondary carboxylic acid amide
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Aromatic alcohol
- Organic oxygen compound
- Aldehyde
- Alcohol
- Carbonyl group
- Organic nitrogen compound
- Hydrocarbon derivative
- Amine
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Primary aliphatic amine
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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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General References | - Wang L, Du D, Li J, Tian Y, Liu H, Niu G, Tan H: [Engineering and heterologous expression of a nikkomycin biosynthetic gene cluster]. Wei Sheng Wu Xue Bao. 2015 Jun 4;55(6):707-18. [PubMed:26562995 ]
- Feng C, Ling H, Du D, Zhang J, Niu G, Tan H: Novel nikkomycin analogues generated by mutasynthesis in Streptomyces ansochromogenes. Microb Cell Fact. 2014 Apr 21;13(1):59. doi: 10.1186/1475-2859-13-59. [PubMed:24751325 ]
- Li J, Li L, Tian Y, Niu G, Tan H: Hybrid antibiotics with the nikkomycin nucleoside and polyoxin peptidyl moieties. Metab Eng. 2011 May;13(3):336-44. doi: 10.1016/j.ymben.2011.01.002. Epub 2011 Feb 1. [PubMed:21292022 ]
- Liao G, Li J, Li L, Yang H, Tian Y, Tan H: Cloning, reassembling and integration of the entire nikkomycin biosynthetic gene cluster into Streptomyces ansochromogenes lead to an improved nikkomycin production. Microb Cell Fact. 2010 Jan 23;9:6. doi: 10.1186/1475-2859-9-6. [PubMed:20096125 ]
- Liao G, Li J, Li L, Yang H, Tian Y, Tan H: Selectively improving nikkomycin Z production by blocking the imidazolone biosynthetic pathway of nikkomycin X and uracil feeding in Streptomyces ansochromogenes. Microb Cell Fact. 2009 Nov 23;8:61. doi: 10.1186/1475-2859-8-61. [PubMed:19930628 ]
- LOTUS database [Link]
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