Common NameAdenosine 3',5'-bisphosphate
DescriptionAdenosine 3', 5'-diphosphate or PAP is a nucleotide that is closely related to ADP. It has two phosphate groups attached to the 5' and 3' positions of the pentose sugar ribose (instead of pyrophosphoric acid at the 5' position, as found in ADP), and the nucleobase adenine. PAP is converted to PAPS by Sulfotransferase and then back to PAP after the sulfotransferase reaction. Sulfotransferase (STs) catalyze the transfer reaction of the sulfate group from the ubiquitous donor 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to an acceptor group of numerous substrates. This reaction, often referred to as sulfuryl transfer, sulfation, or sulfonation, is widely observed from bacteria to humans and plays a key role in various biological processes such as cell communication, growth and development, and defense. PAP also appears to a role in bipolar depression. Phosphatases converting 3'-phosphoadenosine 5'-phosphate (PAP) into adenosine 5'-phosphate are of fundamental importance in living cells as the accumulation of PAP is toxic to several cellular systems. These enzymes are lithium-sensitive and we have characterized a human PAP phosphatase as a potential target of lithium therapy.
Structure
Molecular FormulaC10H15N5O10P2
Average Mass427.20110
Monoisotopic Mass427.02941
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number1053-73-2
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)([O-])[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O
InChI IdentifierInChI=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
InChI KeyWHTCPDAXWFLDIH-KQYNXXCUSA-N
CHEBI IDCHEBI:58343
HMDB IDHMDB0000061
Pathways
NameSMPDB/PathBank
Sulfur metabolism
Starch and sucrose metabolism
Androgen and Estrogen Metabolism
Metachromatic Leukodystrophy (MLD)
Globoid Cell Leukodystrophy
Gaucher Disease
17-Beta Hydroxysteroid Dehydrogenase III Deficiency
Tamoxifen Action Pathway
Fabry disease
Krabbe disease
Sulfite oxidase deficiency
Aromatase deficiency
Tamoxifen Metabolism Pathway
Acetaminophen Metabolism Pathway
Estrone Metabolism
StateSolid
Water Solubility3.33e+00 g/l
logP-1.63
logS-2.11
pKa (Strongest Acidic)0.71
pKa (Strongest Basic)4.92
Hydrogen Acceptor Count12
Hydrogen Donor Count6
Polar Surface Area232.6 Ų
Rotatable Bond Count6
Physiological Charge-4
Formal Charge0
Refractivity84.94 m³·mol⁻¹
Polarizability34.31

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT