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8-Chloroadenosine-5'-triphosphate sodium

CAT: 0931-T83786Size: 2700 μgDry Ice: NoHazardous: No
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CAT#:0931-T83786Size:2700 μg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
793671-47-3
Target
Others, Topoisomerase
Related Pathways
Others, DNA Damage/DNA Repair
Bioactivity
8-Chloroadenosine-5'-triphosphate (8-chloro ATP), a potent metabolite of the anticancer agent 8-chloro cyclic AMP (cAMP) and a nucleotide derivative, is produced through the biotransformation of 8-chloro cAMP into 8-chloroadenosine, followed by mono- and diphosphate intermediates. Accumulating for up to 12 hours after the administration of 8-chloro cAMP or 8-chloroadenosine, 8-chloro ATP inhibits cell growth, diminishes endogenous ATP levels, and reduces RNA synthesis without affecting DNA synthesis in multiple myeloma cells derived from patients. Moreover, it obstructs topoisomerase II-α-mediated relaxation of supercoiled pUC19 DNA at concentrations ranging from 1.5 to 8 mM and decreases topoisomerase II-α-enhanced ATP hydrolysis by 50% at a concentration of 1 mM in K562 human myelocytic leukemia cells.
Smiles
O[C@@H]1[C@@H](COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O)O[C@@H](N2C3=NC=NC(N)=C3N=C2Cl)[C@@H]1O.[Na+].[Na+].[Na+].[Na+]
Molecular Formula
C10H11ClN5O13P3.4Na
Molecular Weight
629.55
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

8-Cl-ATP
CAS Number793671-47-3
PubChem CID56846240
IUPAC Nametetrasodium;[[[(2R,3S,4R,5R)-5-(6-amino-8-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl]oxy-oxidophosphoryl] phosphate
Molecular FormulaC10H11ClN5Na4O13P3
Molecular Weight629.55
Topological Polar Surface Area290
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count17
Rotatable Bond Count7
Heavy Atom Count36
Formal Charge0
Complexity808
SMILES
C1=NC(=C2C(=N1)N(C(=N2)Cl)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])O)O)N.[Na+].[Na+].[Na+].[Na+]
InChI
InChI=1S/C10H15ClN5O13P3.4Na/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21;;;;/h2-3,5-6,9,17-18H,1H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21);;;;/q;4*+1/p-4/t3-,5-,6-,9-;;;;/m1..../s1
InChIKey
BIFUJGGPLKGBNZ-ZVQJTLEUSA-J
Chemical Structure
2D Structure
2D structure of 8-Cl-ATP
CAS: 793671-47-3
CID: 56846240
Formula: C10H11ClN5Na4O13P3
MW: 629.55
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight629.55
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count17
Rotatable Bond Count7
Exact Mass628.8845512
Monoisotopic Mass628.8845512
Topological Polar Surface Area290 Ų
Heavy Atom Count36
Formal Charge0
Complexity808
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count5
Compound Is CanonicalizedYes

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