Record Information |
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Version | 2.0 |
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Created at | 2022-04-28 06:57:38 UTC |
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Updated at | 2022-04-28 06:57:38 UTC |
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NP-MRD ID | NP0062278 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (-)-Aristeromycin |
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Description | Aristeromycin, also known as cycloadenosine, belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base. (-)-Aristeromycin is found in Streptomyces citricolor and Streptomyces citricolor nov. sp.. (-)-Aristeromycin was first documented in 2020 (PMID: 33479662). Based on a literature review a small amount of articles have been published on aristeromycin (PMID: 33792325) (PMID: 33396631) (PMID: 32854369) (PMID: 31841728). |
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Structure | NC1=C2N=CN([C@@H]3C[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1 InChI=1S/C11H15N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h3-6,8-9,17-19H,1-2H2,(H2,12,13,14)/t5-,6-,8-,9+/m1/s1 |
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Synonyms | Value | Source |
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Aristeromycin, (1alpha,2alpha,3beta,5beta)-(+-)-isomer | MeSH | Aristeromycin, (1alpha,2beta,3beta,5beta)-(+-)-isomer | MeSH | Carbocyclic adenosine | MeSH | Cycloadenosine | MeSH |
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Chemical Formula | C11H15N5O3 |
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Average Mass | 265.2730 Da |
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Monoisotopic Mass | 265.11749 Da |
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IUPAC Name | (1R,2S,3R,5R)-3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol |
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Traditional Name | (1R,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol |
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CAS Registry Number | Not Available |
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SMILES | NC1=C2N=CN([C@@H]3C[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1 |
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InChI Identifier | InChI=1S/C11H15N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h3-6,8-9,17-19H,1-2H2,(H2,12,13,14)/t5-,6-,8-,9+/m1/s1 |
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InChI Key | UGRNVLGKAGREKS-GCXDCGAKSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Nucleoside and nucleotide analogues |
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Sub Class | Cyclopentyl nucleosides |
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Direct Parent | 1,3-substituted cyclopentyl purine nucleosides |
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Alternative Parents | |
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Substituents | - 1,3-substituted cyclopentyl purine nucleoside
- 6-aminopurine
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Cyclopentanol
- N-substituted imidazole
- Pyrimidine
- Imidolactam
- Azole
- Cyclic alcohol
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- Azacycle
- Organoheterocyclic compound
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Amine
- Organopnictogen compound
- Alcohol
- Organic nitrogen compound
- Primary amine
- 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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General References | - Vendola AJ, Allais C, Dechert-Schmitt AR, Lee JT, Singer RA, Morken JP: Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin. Org Lett. 2021 Apr 16;23(8):2863-2867. doi: 10.1021/acs.orglett.1c00353. Epub 2021 Apr 1. [PubMed:33792325 ]
- Samunuri R, Toyama M, Pallaka RS, Neeladri S, Jha AK, Baba M, Bal C: Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin. RSC Med Chem. 2020 May 15;11(5):597-601. doi: 10.1039/d0md00059k. eCollection 2020 May 1. [PubMed:33479662 ]
- Santana AC, Silva Filho RC, Menezes JCJMDS, Allonso D, Campos VR: Nitrogen-Based Heterocyclic Compounds: A Promising Class of Antiviral Agents against Chikungunya Virus. Life (Basel). 2020 Dec 30;11(1):16. doi: 10.3390/life11010016. [PubMed:33396631 ]
- Chen Q, Schneller SW, Liu C, Jones KL, Singer T: 5'-Nor-3-Deaza-1',6'-Isoneplanocin, the Synthesis and Antiviral Study. Molecules. 2020 Aug 25;25(17):3865. doi: 10.3390/molecules25173865. [PubMed:32854369 ]
- Shin YS, Jarhad DB, Jang MH, Kovacikova K, Kim G, Yoon JS, Kim HR, Hyun YE, Tipnis AS, Chang TS, van Hemert MJ, Jeong LS: Identification of 6'-beta-fluoro-homoaristeromycin as a potent inhibitor of chikungunya virus replication. Eur J Med Chem. 2020 Feb 1;187:111956. doi: 10.1016/j.ejmech.2019.111956. Epub 2019 Dec 9. [PubMed:31841728 ]
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