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
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.
DBLinks
- CAS Registry Number: 1053-73-2
- PubChem CID: 159296
- ChEBI: 17985
- HMDB: HMDB0000061
- LipidMaps:
- KEGG: C00054
- BioCyc:
- NCBI MeSH: adenosine 3'-phosphate-5'-phosphate
- Wikipedia: Adenosine_3%27,5%27-bisphosphate
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
- WishartLab ClassyFire: [Purine ribonucleotides] Purine ribonucleotides
- RefMet: [Purine rNDP] Purine rNDP
- ChEBI: [CHEBI:17985] adenosine 3',5'-bismonophosphate
| 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 |
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 |