Chemistry:Adenosine 3',5'-bisphosphate

Adenosine 3',5'-bisphosphate

Names
IUPAC name Adenosine 3′,5′-bis(dihydrogen phosphate)
Systematic IUPAC name (2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-2-[(phosphonooxy)methyl]oxolan-3-yl dihydrogen phosphate
Other names 3'-Phosphoadenylate
Identifiers
CAS Number	1053-73-2 Y
3D model (JSmol)	Interactive image
ChemSpider	140102 N
IUPHAR/BPS	1718
MeSH	Adenosine+bisphosphate
PubChem CID	159296
UNII	C65F80D52U Y
InChI InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1 N Key: WHTCPDAXWFLDIH-KQYNXXCUSA-N N InChI=1/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1 Key: WHTCPDAXWFLDIH-KQYNXXCUBO
SMILES c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)OP(=O)(O)O)O)N
Properties
Chemical formula	C10H15N5O10P2
Molar mass	427.20 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Tracking categories (test):

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Adenosine 3',5'-bisphosphate is a form of an adenosine nucleotide with two phosphate groups attached to different carbons in the ribose ring. This is distinct from adenosine diphosphate, where the two phosphate groups are attached in a chain to the 5' carbon atom in the ring.

Adenosine 3',5'-bisphosphate is produced as a product of sulfotransferase enzymes from the donation of a sulfate group from the coenzyme 3'-phosphoadenosine-5'-phosphosulfate. This product is then hydrolysed by 3'(2'),5'-bisphosphate nucleotidase to give adenosine monophosphate, which can then be recycled into adenosine triphosphate.

See also

• Adenine
• Sulfur metabolism
• Acetyl-CoA