AraCTP
Basic information
- CAS
13191-15-6- Standard SMILES
Nc1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@@H]2O)c(=O)n1- InChIKey
PCDQPRRSZKQHHS-CCXZUQQUSA-N- Molecular formula
- C9H16N3O14P3
- Average molar mass
- 483.16 g/mol
- Monoisotopic mass
- 482.98451319
Overview
Arabinofuranosylcytosine Triphosphate is a triphosphate nucleotide analog that is the metabolized, biologically active form of cytarabine. This metabolite is a competitive inhibitor of DNA synthesis.
Names & identifiers
- Preferred name
- AraCTP
- IUPAC
- [[(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
- English name
- Ara-C triphosphate
- Molecular formula
- C9H16N3O14P3
- Molecular weight
- 483.16
Names & synonyms
13191-15-6Arabinofuranosylcytosine triphosphateAra-CTPCytosine arabinoside triphosphateArabinosylcytosine triphosphateArabinosylcytosine 5'-triphosphateAraCTPAra CTPS78SFW950ODTXSID409273882(1H)-Pyrimidinone, 4-amino-1-(5-O-(hydroxy((hydroxy(phosphonooxy)phosphinyl)oxy)phosphinyl)-beta-D-arabinofuranosyl)-Triphosphate, Cytarabine
Show more names
ara-CTP·Na3ara-Cytidine-5'-triphosphate (ara-CTP)ara-Cytidine-5′,-triphosphate (ara-CTP), L packara-Cytidine-5′,-triphosphate (ara-CTP), S packAra-cytidine-5'-triphosphate (ara-CTP) (aqueous solution)Ara-cytidine-5'-triphosphate sodium salt(Ara-CTP trisodium) (aqueous solution)Ara-cytidine-5'-triphosphate (ara-CTP) (aqueous solution), DNA synthesis inhibitor
RefChem:113659Triphosphate, ArabinosylcytosineTriphosphate, Cytosine ArabinosideDTXCID601356179Triphosphate, ArabinofuranosylcytosineCytarabine Triphosphate[[(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphateAra-C triphosphate
Properties
Computed structural properties
- XLogP
- -5.6
- Topological polar surface area
- 268 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 8
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 855
Physicochemical properties
- Boiling point
- 849.2 · 849.2±75.0 °C(Predicted)
- Density
- 2.5 · 2.50±0.1 g/cm3(Predicted)
- pka
- 0.97 · 0.97±0.50(Predicted)
- form
- Solid
- color
- White to off-white
- FDA UNII
- 78 SFW950O · S78SFW950O
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds that inhibit cell production of DNA or RNA.
Applications
UsesCytarabine triphosphate (Ara-CTP), an active metabolite of Cytarabine, is a competitive inhibitor of DNA synthesis. Intracellular Cytarabine triphosphate levels can be used to predict chemosensitivity of leukemic blasts to Cytarabine[1].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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