Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:42:20 UTC |
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Updated at | 2021-08-12 19:52:22 UTC |
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NP-MRD ID | NP0002865 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 2,3-Dideoxycytidine |
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Provided By | BMRB |
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Description | Zalcitabine, also known as DDC or hivid, belongs to the class of organic compounds known as pyrimidine 2',3'-dideoxyribonucleosides. Pyrimidine 2',3'-dideoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at positions 2 and 3. Zalcitabine is a drug which is used for the treatment of human immunovirus (hiv) infections in conjunction with other antivirals. In humans, zalcitabine is involved in the zalcitabine action pathway. Zalcitabine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Zalcitabine is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. It was first documented in 1993 (PMID: 8097417). Based on a literature review a significant number of articles have been published on Zalcitabine (PMID: 17984079) (PMID: 7614775) (PMID: 11905988) (PMID: 7727578). |
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Structure | NC1=NC(=O)N(C=C1)[C@H]1CC[C@@H](CO)O1 InChI=1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1 |
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Synonyms | Value | Source |
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2',3'-Dideoxycytidine | ChEBI | 4-Amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one | ChEBI | DDC | ChEBI | DDCYD | ChEBI | Dideoxycytidine | ChEBI | Hivid | Kegg | ABBR DDC | Kegg | HIVID roche | HMDB | 2',3' Dideoxycytidine | HMDB | Hoffman-la roche brand OF zalcitabine | HMDB | Roche brand OF zalcitabine | HMDB | DDC (Antiviral) | HMDB |
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Chemical Formula | C9H13N3O3 |
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Average Mass | 211.2178 Da |
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Monoisotopic Mass | 211.09569 Da |
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IUPAC Name | 4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one |
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Traditional Name | zalcitabine |
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CAS Registry Number | Not Available |
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SMILES | NC1=NC(=O)N(C=C1)[C@H]1CC[C@@H](CO)O1 |
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InChI Identifier | InChI=1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1 |
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InChI Key | WREGKURFCTUGRC-POYBYMJQSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 pyrimidine 2',3'-dideoxyribonucleosides. Pyrimidine 2',3'-dideoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at positions 2 and 3. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleosides |
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Sub Class | Pyrimidine 2',3'-dideoxyribonucleosides |
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Direct Parent | Pyrimidine 2',3'-dideoxyribonucleosides |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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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 | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Devineni D, Gallo JM: Zalcitabine. Clinical pharmacokinetics and efficacy. Clin Pharmacokinet. 1995 May;28(5):351-60. doi: 10.2165/00003088-199528050-00002. [PubMed:7614775 ]
- Shelton MJ, O'Donnell AM, Morse GD: Zalcitabine. Ann Pharmacother. 1993 Apr;27(4):480-9. doi: 10.1177/106002809302700416. [PubMed:8097417 ]
- Gibbs JE, Thomas SA: The distribution of the anti-HIV drug, 2'3'-dideoxycytidine (ddC), across the blood-brain and blood-cerebrospinal fluid barriers and the influence of organic anion transport inhibitors. J Neurochem. 2002 Feb;80(3):392-404. doi: 10.1046/j.0022-3042.2001.00711.x. [PubMed:11905988 ]
- Torres RA, Barr MR, McIntyre KI, Thornton JR, Shay WM, Feldman RD, George NJ, Britton DJ: A comparison of zidovudine, didanosine, zalcitabine and no antiretroviral therapy in patients with advanced HIV disease. Int J STD AIDS. 1995 Jan-Feb;6(1):19-26. doi: 10.1177/095646249500600105. [PubMed:7727578 ]
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