2',3'-Dideoxyadenosine 5'-Triphosphate - CAS 24027-80-3
Catalog: |
BB018295 |
Product Name: |
2',3'-Dideoxyadenosine 5'-Triphosphate |
CAS: |
24027-80-3 |
Synonyms: |
[[(2S,5R)-5-(6-aminopurin-9-yl)-2-oxolanyl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate; [[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate |
Application: |
ddATP is an inhibitor of reverse transcriptases from retroviruses. |
IUPAC Name: | [[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate |
Description: | ddATP is an inhibitor of reverse transcriptases from retroviruses, such as HIV-1 and visna (Kis = 20 and 37 nM, respectively). ddATP is commonly used to terminate chain extension produced by the Taq polymerase for its competitive effect with dATP in cells. |
Molecular Weight: | 475.18 |
Molecular Formula: | C10H16N5O11P3 |
Canonical SMILES: | C1CC(OC1COP(=O)(O)OP(=O)(O)OP(=O)(O)O)N2C=NC3=C2N=CN=C3N |
InChI: | InChI=1S/C10H16N5O11P3/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(24-7)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h4-7H,1-3H2,(H,19,20)(H,21,22)(H2,11,12,13)(H2,16,17,18)/t6-,7+/m0/s1 |
InChI Key: | OAKPWEUQDVLTCN-NKWVEPMBSA-N |
Purity: | ≥ 98 % by HPLC |
Solubility: | In vitro: 10 mM in DMSO |
Appearance: | Clear aqueous solution |
Storage: | Store at -20°C or below |
LogP: | 1.01060 |
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PMID | Publication Date | Title | Journal |
23094055 | 20120101 | VS411 reduced immune activation and HIV-1 RNA levels in 28 days: randomized proof-of-concept study for antiviral-hyperactivation limiting therapeutics | PloS one |
20164190 | 20100416 | The acyclic 2,4-diaminopyrimidine nucleoside phosphonate acts as a purine mimetic in HIV-1 reverse transcriptase DNA polymerization | The Journal of biological chemistry |
19837673 | 20091218 | Mechanism of inhibition of HIV-1 reverse transcriptase by 4'-Ethynyl-2-fluoro-2'-deoxyadenosine triphosphate, a translocation-defective reverse transcriptase inhibitor | The Journal of biological chemistry |
19467308 | 20090911 | Metabolism evaluation of biomimetic prodrugs by in vitro models and mass spectrometry | International journal of pharmaceutics |
19596885 | 20090901 | Anti-human immunodeficiency virus activity, cross-resistance, cytotoxicity, and intracellular pharmacology of the 3'-azido-2',3'-dideoxypurine nucleosides | Antimicrobial agents and chemotherapy |
Complexity: | 738 |
Compound Is Canonicalized: | Yes |
Covalently-Bonded Unit Count: | 1 |
Defined Atom Stereocenter Count: | 2 |
Defined Bond Stereocenter Count: | 0 |
Exact Mass: | 475.00591734 |
Formal Charge: | 0 |
Heavy Atom Count: | 29 |
Hydrogen Bond Acceptor Count: | 15 |
Hydrogen Bond Donor Count: | 5 |
Isotope Atom Count: | 0 |
Monoisotopic Mass: | 475.00591734 |
Rotatable Bond Count: | 8 |
Topological Polar Surface Area: | 239 |
Undefined Atom Stereocenter Count: | 0 |
Undefined Bond Stereocenter Count: | 0 |
XLogP3: | -3.5 |
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