Record Information |
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Version | 2.0 |
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Created at | 2022-09-02 15:15:03 UTC |
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Updated at | 2022-09-02 15:15:03 UTC |
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NP-MRD ID | NP0157783 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | spiramycin ii |
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Description | Spiramycin II, also known as foromacidin b or acetylspiramycin, belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Thus, spiramycin II is considered to be an ansamycin. Spiramycin II 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. spiramycin ii was first documented in 1990 (PMID: 2232146). Based on a literature review a significant number of articles have been published on spiramycin II (PMID: 28278108) (PMID: 20490499) (PMID: 19306580) (PMID: 15127585) (PMID: 16496680) (PMID: 20843520). |
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Structure | CO[C@H]1[C@@H](CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O[C@H]2CC[C@@H]([C@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](O)[C@H](C)O2)[C@@H]([C@H]1O)N(C)C)OC(C)=O InChI=1S/C45H76N2O15/c1-25-22-31(20-21-48)41(62-44-39(51)38(47(10)11)40(28(4)58-44)61-37-24-45(7,53)43(52)29(5)57-37)42(54-12)34(59-30(6)49)23-35(50)55-26(2)16-14-13-15-17-33(25)60-36-19-18-32(46(8)9)27(3)56-36/h13-15,17,21,25-29,31-34,36-44,51-53H,16,18-20,22-24H2,1-12H3/b14-13+,17-15+/t25-,26-,27+,28-,29+,31+,32+,33+,34-,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1 |
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Synonyms | Value | Source |
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Acetylspiramycin | ChEBI | Acetylspiramycinum | ChEBI | Foromacidin b | ChEBI | Foromacidine b | ChEBI | Spiramycin 2 | ChEBI | Spiramycin b | ChEBI |
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Chemical Formula | C45H76N2O15 |
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Average Mass | 885.1020 Da |
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Monoisotopic Mass | 884.52457 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | CO[C@H]1[C@@H](CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O[C@H]2CC[C@@H]([C@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](O)[C@H](C)O2)[C@@H]([C@H]1O)N(C)C)OC(C)=O |
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InChI Identifier | InChI=1S/C45H76N2O15/c1-25-22-31(20-21-48)41(62-44-39(51)38(47(10)11)40(28(4)58-44)61-37-24-45(7,53)43(52)29(5)57-37)42(54-12)34(59-30(6)49)23-35(50)55-26(2)16-14-13-15-17-33(25)60-36-19-18-32(46(8)9)27(3)56-36/h13-15,17,21,25-29,31-34,36-44,51-53H,16,18-20,22-24H2,1-12H3/b14-13+,17-15+/t25-,26-,27+,28-,29+,31+,32+,33+,34-,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1 |
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InChI Key | ZPCCSZFPOXBNDL-RSMXASMKSA-N |
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Experimental Spectra |
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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 |
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Chemical Shift Submissions |
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| Not Available |
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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 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
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Dicarboxylic acid or derivatives
- Oxane
- Alpha-hydrogen aldehyde
- Tertiary alcohol
- Carboxylic acid ester
- 1,2-aminoalcohol
- Lactone
- Amino acid or derivatives
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Dialkyl ether
- Organoheterocyclic compound
- Carboxylic acid derivative
- Oxacycle
- Ether
- Acetal
- Organic oxide
- Carbonyl group
- Organic nitrogen compound
- Organopnictogen compound
- Amine
- Alcohol
- Aldehyde
- Organonitrogen compound
- Hydrocarbon derivative
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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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External Links |
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HMDB ID | Not Available |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4445368 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 5282173 |
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PDB ID | Not Available |
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ChEBI ID | 31168 |
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Good Scents ID | Not Available |
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References |
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General References | - Li Z, Hu F, Ye R, Lv H, Zeng J: Influence of Al(3+) on the titer of spiramycin and effective components in fermentor. Prep Biochem Biotechnol. 2017 May 28;47(5):481-488. doi: 10.1080/10826068.2017.1292290. Epub 2017 Feb 17. [PubMed:28278108 ]
- Ma C, Zhou H, Li J, Dai J, He W, Wang H, Wu L, Wang Y: Construction of 4"-isovalerylspiramycin-I-producing strain by in-frame partial deletion of 3-O-acyltransferase gene in Streptomyces spiramyceticus WSJ-1, the bitespiramycin producer. Curr Microbiol. 2011 Jan;62(1):16-20. doi: 10.1007/s00284-010-9664-8. Epub 2010 May 19. [PubMed:20490499 ]
- Ma C, Wu L, Dai J, Zhou H, Li J, Sun X, Zhang K, Xia H, Wang Y: [Acylation specificity of midecamycin 3-O-acyltransferase within Streptomyces spiramyceticus F21]. Sheng Wu Gong Cheng Xue Bao. 2008 Dec;24(12):2086-92. [PubMed:19306580 ]
- Luan XJ, Song ZH, Xiao Z: Monitoring sub-nanogram amount of acetylspiramycin in human urine using flow injection analysis with chemiluminescence detection. Yao Xue Xue Bao. 2004 Jan;39(1):64-7. [PubMed:15127585 ]
- Wang FM: [Parallel catalytic hydrogen wave of acetylspiramycin caused by dissolved oxygen and its application]. Yao Xue Xue Bao. 2005 Dec;40(12):1135-8. [PubMed:16496680 ]
- Wang MJ, Pendela M, Hu CQ, Jin SH, Hoogmartens J, Van Schepdael A, Adams E: Impurity profiling of acetylspiramycin by liquid chromatography-ion trap mass spectrometry. J Chromatogr A. 2010 Oct 15;1217(42):6531-44. doi: 10.1016/j.chroma.2010.08.061. Epub 2010 Sep 16. [PubMed:20843520 ]
- Kondo A, Nakatani T, Kuzuya Y, Suzuki H, Sano H, Yamaguchi K, Shirahata K, Takahashi K, Kita K, Nishiie Y, et al.: [Studies on acetylspiramycin. 1. Separation and chemical structures of acetylspiramycin components]. Jpn J Antibiot. 1990 Jun;43(6):1152-63. [PubMed:2232146 ]
- Yang AM, Song JH, Huang R, Jin SJ, Yang P: [Mycoplasma pneumoniae infection and drug resistance in children: an analysis of 1026 cases]. Zhongguo Dang Dai Er Ke Za Zhi. 2013 Jul;15(7):522-5. [PubMed:23866271 ]
- Arai H, Sakai T, Okano K, Aoyagi R, Imai A, Takase H, Mochizuki M, Tsuneoka H: Presumed toxoplasmic central retinal artery occlusion and multifocal retinitis with perivascular sheathing. Clin Ophthalmol. 2014 Apr 23;8:789-92. doi: 10.2147/OPTH.S58669. eCollection 2014. [PubMed:24790408 ]
- Wang QY, Li RH, Zheng LQ, Shang XH: Prevalence and antimicrobial susceptibility of Ureaplasma urealyticum and Mycoplasma hominis in female outpatients, 2009-2013. J Microbiol Immunol Infect. 2016 Jun;49(3):359-62. doi: 10.1016/j.jmii.2014.06.007. Epub 2014 Jul 28. [PubMed:25081985 ]
- LOTUS database [Link]
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