Adenosine 3',5'-diphosphate (ECMDB00061) (M2MDB000022)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 09:56:27 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:05 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Adenosine 3',5'-diphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 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 3'-phosphoadenosine 5'-phosphosulfate (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 plays a key role in various biological processes such as cell communication, growth and development, and defense. (HMDB) PAP is involved in sulfur metabolism in E. coli, and can be converted into AMP and subsequently ADP by enzymes. (PMID 10939241) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C10H15N5O10P2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 427.2011 Monoisotopic: 427.029414749 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | WHTCPDAXWFLDIH-KQYNXXCUSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 1053-73-2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | adenosine 3',5'-bisphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Purine ribonucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Purine ribonucleoside 3',5'-bisphosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | glutaredoxin + Phosphoadenosine phosphosulfate > glutaredoxin +2 Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite Phosphoadenosine phosphosulfate + Reduced Thioredoxin >2 Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite + Oxidized Thioredoxin apoprotein [acyl carrier protein] + Coenzyme A > acyl carrier protein + Hydrogen ion + Adenosine 3',5'-diphosphate Water + Adenosine 3',5'-diphosphate > Adenosine monophosphate + Phosphate Coenzyme A + Apo-[acyl-carrier-protein] <> Adenosine 3',5'-diphosphate + Acyl-carrier protein + Acyl-carrier protein Thioredoxin + Phosphoadenosine phosphosulfate + Thioredoxin disulfide <> Thioredoxin disulfide + Sulfite + Adenosine 3',5'-diphosphate + Thioredoxin CoA-(4'-phosphopantetheine) + apo-[acyl-carrier-protein] > Adenosine 3',5'-diphosphate + holo-[acyl-carrier-protein] CoA + [protein-X] > Adenosine 3',5'-diphosphate + phosphopantetheinyl-[protein-X] Adenosine 3',5'-diphosphate + Sulfite + thioredoxin disulfide > Phosphoadenosine phosphosulfate + thioredoxin Adenosine 3',5'-diphosphate + Water > Adenosine monophosphate + Inorganic phosphate CoA + apo-EntB/F > Adenosine 3',5'-diphosphate + holo-EntB/F Adenosine 3',5'-diphosphate + Water <> Adenosine monophosphate + Phosphate Phosphoadenosine phosphosulfate + reduced thioredoxin > Sulfite +2 Hydrogen ion + Adenosine 3',5'-diphosphate +2 oxidized thioredoxin + Sulfite + Adenosine 3',5'-diphosphate Phosphoadenosine phosphosulfate + reduced thioredoxin > Sulfite + oxidized thioredoxin + Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite + Adenosine 3',5'-diphosphate Thioredoxin + Phosphoadenosine phosphosulfate + Thioredoxin disulfide <> Sulfite + Adenosine 3',5'-diphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Tsunako, Mitsutomo; Kotone, Akira. Preparation of nucleoside-2',5'- and 3',5'-diphosphoric acids. Jpn. Kokai Tokkyo Koho (1991), 13 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in electron carrier activity
- Specific function:
- Efficient electron donor for the essential enzyme ribonucleotide reductase. Is also able to reduce the interchain disulfide bridges of insulin
- Gene Name:
- trxC
- Uniprot ID:
- P0AGG4
- Molecular weight:
- 15555
Reactions
Protein dithiol + NAD(P)(+) = protein disulfide + NAD(P)H. |
- General function:
- Involved in phosphoadenylyl-sulfate reductase (thioredoxin) activity
- Specific function:
- Reduction of activated sulfate into sulfite
- Gene Name:
- cysH
- Uniprot ID:
- P17854
- Molecular weight:
- 27976
Reactions
Adenosine 3',5'-bisphosphate + sulfite + thioredoxin disulfide = 3'-phosphoadenylyl sulfate + thioredoxin. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Catalyzes the transfer of the 4'-phosphopantetheine moiety from coenzyme A to apo-domains of both entB (an ArCP domain) and entF (a PCP domain). Plays an essential role in the assembly of the enterobactin
- Gene Name:
- entD
- Uniprot ID:
- P19925
- Molecular weight:
- 23604
Reactions
CoA + apo-EntB/F = adenosine 3',5'-bisphosphate + holo-EntB/F. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Converts 3'(2')-phosphoadenosine 5'-phosphate (PAP) to AMP. May also convert adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS). Has 10000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2)
- Gene Name:
- cysQ
- Uniprot ID:
- P22255
- Molecular weight:
- 27176
Reactions
Adenosine 3',5'-bisphosphate + H(2)O = adenosine 5'-phosphate + phosphate. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Transfers the 4'-phosphopantetheine moiety from coenzyme A to the 'Ser-36' of acyl-carrier-protein
- Gene Name:
- acpS
- Uniprot ID:
- P24224
- Molecular weight:
- 14052
Reactions
CoA-(4'-phosphopantetheine) + apo-[acyl-carrier-protein] = adenosine 3',5'-bisphosphate + holo-[acyl-carrier-protein]. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- May be involved in an alternative pathway for phosphopantetheinyl transfer and holo-ACP synthesis in E.coli. The native apo-protein substrate is unknown. Is able to functionally replace AcpS in vivo but only when expressed at high levels
- Gene Name:
- acpT
- Uniprot ID:
- P37623
- Molecular weight:
- 21768
Reactions
CoA + [protein-X] = adenosine 3',5'-bisphosphate + phosphopantetheinyl-[protein-X]. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Monothiol glutaredoxin involved in the biogenesis of iron-sulfur clusters (Probable)
- Gene Name:
- grxD
- Uniprot ID:
- P0AC69
- Molecular weight:
- 12879
- General function:
- Involved in electron carrier activity
- Specific function:
- The disulfide bond functions as an electron carrier in the glutathione-dependent synthesis of deoxyribonucleotides by the enzyme ribonucleotide reductase. In addition, it is also involved in reducing some disulfides in a coupled system with glutathione reductase
- Gene Name:
- grxC
- Uniprot ID:
- P0AC62
- Molecular weight:
- 9137
- General function:
- Involved in protein binding
- Specific function:
- Involved in reducing some disulfides in a coupled system with glutathione reductase. Does not act as hydrogen donor for ribonucleotide reductase
- Gene Name:
- grxB
- Uniprot ID:
- P0AC59
- Molecular weight:
- 24350
- General function:
- Involved in electron carrier activity
- Specific function:
- The disulfide bond functions as an electron carrier in the glutathione-dependent synthesis of deoxyribonucleotides by the enzyme ribonucleotide reductase. In addition, it is also involved in reducing some disulfides in a coupled system with glutathione reductase
- Gene Name:
- grxA
- Uniprot ID:
- P68688
- Molecular weight:
- 9685
- General function:
- Involved in electron carrier activity
- Specific function:
- Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions
- Gene Name:
- trxA
- Uniprot ID:
- P0AA25
- Molecular weight:
- 11807