Adenosine 3',5'-bisphosphate (BioCAD00000005891)

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Metabolite Card

Formula: C10H15N5O10P2 (427.0294)
SMILES: NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1

Synonyms [en]

Adenosine 3',5'-bisphosphate; Phosphoadenosine phosphate; 3'-phosphoadenylate; PAP; adenosine 3',5'-diphosphate; adenosine 3',5'-bismonophosphate

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Adenosine 3',5'-bisphosphate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000005891). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Adenosine 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.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 1053-73-2
  • PubChem: 159296
  • ChEBI: ChEBI:17985
  • HMDB: HMDB0000061
  • KEGG: C00054
  • NCBI MeSH: adenosine 3'-phosphate-5'-phosphate
  • Wikipedia: Adenosine_3%27,5%27-bisphosphate
  • DrugBank: DB01812
  • RefMet: RM0135875
  • MoNA: MoNA001932
  • MoNA: MoNA001933
  • MoNA: MoNA001934
  • MoNA: MoNA034044
  • MoNA: MoNA034045
  • MoNA: MoNA034047
  • MoNA: MoNA037876
  • MoNA: PS011301
  • MoNA: PS011302
  • MoNA: PS011303
  • MoNA: PS011304
  • MoNA: PS011305
  • MoNA: PS011306
  • MoNA: PS011307
  • MoNA: PS011308
  • MoNA: PS011310
  • MoNA: PS011311
  • Metlin: METLIN_3533

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00188 3.1.3.7 adenosine-3',5'-bisphosphate 3'-phosphohydrolase
KEGG:R00507 3.6.2.2 3'-phosphoadenylyl-sulfate sulfohydrolase;
KEGG:R00535 2.8.2.15 3'-phosphoadenylylsulfate:17beta-estradiol 3-sulfotransferase
KEGG:R00536 2.8.2.15 3'-phosphoadenylylsulfate:phenolic-steroid sulfotransferase
KEGG:R00537 2.8.2.15 3'-phosphoadenylylsulfate:phenolic-steroid sulfotransferase
KEGG:R00629 2.8.2.2 3'-phosphoadenylyl-sulfate:alcohol sulfotransferase
KEGG:R01027 2.8.2.6 3'-phosphoadenylyl-sulfate:choline sulfotransferase
KEGG:R01236 2.8.2.16 3'-phosphoadenylylsulfate:thiol S-sulfotransferase
KEGG:R01242 2.8.2.1 3'-phosphoadenylylsulfate:phenol sulfotransferase
KEGG:R01625 2.7.8.7 CoA:apo-[acyl-carrier-protein] pantetheinephosphotransferase
KEGG:R01861 2.8.2.3 3'-phosphoadenylyl-sulfate:benzenamine N-sulfotransferase
KEGG:R02021 1.8.4.8 adenosine 3',5'-bisphosphate,sulfite:oxidized-thioredoxin oxidoreductase (3'-phosphoadenosine-5'-phosphosulfate -forming)
KEGG:R02122 2.8.2.8 3'-phosphoadenylyl-sulfate:[heparan sulfate]-glucosamine N-sulfotransferase
KEGG:R02159 2.8.2.25 3'-phosphoadenylylsulfate:quercetin 3-sulfotransferase
KEGG:R02180 2.8.2.5 3'-phosphoadenylylsulfate:chondroitin 4'-sulfotransferase
KEGG:R02181 2.8.2.17 3'-phosphoadenylylsulfate:chondroitin 6'-sulfotransferase
KEGG:R02350 2.8.2.4 3'-phosphoadenylylsulfate:estrone 3-sulfotransferase
KEGG:R02586 2.8.2.20 3'-phosphoadenylylsulfate:protein-tyrosine O-sulfotransferase
KEGG:R02632 2.8.2.26 3'-phosphoadenylylsulfate:quercetin-3-sulfate 3'-sulfotransferase
KEGG:R02633 2.8.2.27 3'-phosphoadenylylsulfate:quercetin-3-sulfate 4'-sulfotransferase
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:CALBI_PWY-781 sulfate assimilation
BioCyc:TRYPANO_SO4ASSIM-PWY sulfate reduction I (assimilatory)
PathBank:SMP0000821 Cysteine Biosynthesis
PathBank:SMP0000939 Sulfur Metabolism
PathBank:SMP0000940 Sulfur Metabolism (Butanesulfonate)
PathBank:SMP0000941 Sulfur Metabolism (Propanesulfonate)
PathBank:SMP0000942 Sulfur Metabolism (Ethanesulfonate)
PathBank:SMP0000943 Sulfur Metabolism (Isethionate)
PathBank:SMP0000944 Sulfur Metabolism (Methanesulfonate)
WikiPathways:WP1276 Glucuronidation
WikiPathways:WP3264 Tamoxifen metabolism
WikiPathways:WP3604 Biochemical pathways: part I
WikiPathways:WP692 Sulfation biotransformation reaction
WikiPathways:WP698 Glucuronidation
WikiPathways:WP5348 11p11.2 copy number variation syndrome
WikiPathways:WP691 Tamoxifen metabolism
WikiPathways:WP3210 Glucuronidation
WikiPathways:WP3234 Sulfation biotransformation reaction
WikiPathways:WP4784 Proteoglycan biosynthesis
WikiPathways:WP1241 Glucuronidation
View All Pathways