Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:11 UTC |
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Update date | 2019-11-26 02:56:50 UTC |
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Primary ID | FDB001979 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Cytarabine |
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Description | Isolated from the mushroom Xerocomus nigromaculatus of unknown palatability
Cytarabine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute myelogenous leukemia and meningeal leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Cytarabine is metabolized intracellularly into its active triphosphate form (cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA repair through an effect on beta-DNA polymerase, and incorporation into DNA. The latter mechanism is probably the most important. Cytotoxicity is highly specific for the S phase of the cell cycle.; Cytarabine, or cytosine arabinoside, is a chemotherapy agent used mainly in the treatment of hematological malignancies such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma. It is also known as ara C.; Cytosine arabinoside is an antimetabolic agent with the chemical name of 1?-arabinofuranosylcytosine. Its mode of action is due to its rapid conversion into cytosine arabinoside triphosphate, which damages DNA when the cell cycle holds in the S phase (synthesis of DNA). Rapidly dividing cells, which require DNA replication for mitosis, are therefore most affected. Cytosine arabinoside also inhibits both DNA and RNA polymerases and nucleotide reductase enzymes needed for DNA synthesis. Cytarabine is found in mushrooms. |
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CAS Number | 147-94-4 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C9H13N3O5 |
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IUPAC name | 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one |
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InChI Identifier | InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16) |
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InChI Key | UHDGCWIWMRVCDJ-UHFFFAOYSA-N |
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Isomeric SMILES | OCC1OC(C(O)C1O)N1C=CC(=N)N=C1O |
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Average Molecular Weight | 243.2166 |
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Monoisotopic Molecular Weight | 243.085520541 |
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Classification |
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Description | Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. |
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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 | Not Available |
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Direct Parent | Pyrimidine nucleosides |
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Alternative Parents | |
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Substituents | - Pyrimidine nucleoside
- Glycosyl compound
- N-glycosyl compound
- Pentose monosaccharide
- Aminopyrimidine
- Pyrimidone
- Hydropyrimidine
- Monosaccharide
- Pyrimidine
- Imidolactam
- Tetrahydrofuran
- Heteroaromatic compound
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Primary alcohol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Cytarabine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05dl-9310000000-baa27af3867d7b2962e5 | Spectrum | Predicted GC-MS | Cytarabine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_3_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cytarabine, TMS_3_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-03di-0900000000-4d7ac7a2020f3bcdb8af | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4l-0950000000-9d2635dbd5dba4335642 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0900000000-0beed630d191c3ddf484 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-b5174fb5250877fc4322 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0910000000-36ec7f4bb0f43c1bea01 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-4900000000-9df78eed4f14088c8271 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dj-9600000000-73e430a902e254bcf1a5 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0btd-0930000000-7dddc27b279db10b55f1 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03dl-5920000000-ba0a861002b9566db684 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-1a8e142cab2f41210227 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0910000000-ebba965cb6de7bb5887e | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-1910000000-c30c0903bd3816dc1da4 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-5900000000-8cae3c9126ea35107cde | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-006x-0590000000-34c91e737fe5299bafd8 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03dl-4910000000-751c4dfb7474605dd469 | 2021-10-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9200000000-284eea506bf71a5900d1 | 2021-10-12 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 6017 |
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ChEMBL ID | CHEMBL803 |
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KEGG Compound ID | C02961 |
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Pubchem Compound ID | 6253 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28680 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00987 |
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HMDB ID | HMDB15122 |
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CRC / DFC (Dictionary of Food Compounds) ID | HDV37-I:CBW05-L |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | AR3 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Cytarabine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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