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Identification
YMDB IDYMDB00349
NameAdenosine 3',5'-diphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAdenosine 3',5'-diphosphate, also known as 3'-phosphoadenylate or PAP, 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. Adenosine 3',5'-diphosphate is a strong basic compound (based on its pKa). Adenosine 3',5'-diphosphate exists in all living species, ranging from bacteria to humans. sulfite and adenosine 3',5'-diphosphate can be biosynthesized from phosphoadenosine phosphosulfate through the action of the enzyme 3'-phospho-adenylylsulfate reductase. In yeast, adenosine 3',5'-diphosphate is involved in the metabolic pathway called the sulfur metabolism pathway.
Structure
Thumb
Synonyms
  • 3-Phosphoadenosine 5-phosphate
  • 3,5-ADP
  • 3,5-Diphosphoadenosine
  • 3'-Phosphoryl-AMP
  • 5-(dihydrogen phosphate) 3-Adenylate
  • 5-(dihydrogen phosphate)3'-Adenylic acid
  • Adenosine 3,5-bis
  • Adenosine 3,5-bisphosphate
  • Adenosine 3,5-diphosphic acid
  • adenosine 3',5'-bisphosphate
  • 3'-Phosphoadenylate
  • PAP
  • Phosphoadenosine phosphate
  • 3'-Phosphoadenylic acid
  • Adenosine 3',5'-bisphosphoric acid
  • Phosphoadenosine phosphoric acid
  • Adenosine 3',5'-diphosphoric acid
  • Adenosine 3'-phosphate-5'-phosphate, disodium salt
  • 3'-Phosphoadenosine 5'-phosphate
  • Adenosine 3'-phosphate-5'-phosphate, monosodium salt
  • 3',5'-ADP
  • Adenosine 3'-phosphate-5'-phosphate
CAS number1053-73-2
WeightAverage: 427.2011
Monoisotopic: 427.029414749
InChI KeyWHTCPDAXWFLDIH-KQYNXXCUSA-N
InChIInChI=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
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 Nameadenosine 3',5'-bisphosphate
Chemical FormulaC10H15N5O10P2
SMILES[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]1([H])OP(=O)(O[H])O[H])N1C([H])=NC2=C1N=C([H])N=C2N([H])[H]
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside 3',5'-bisphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Phosphoric acid ester
  • Monosaccharide
  • Imidolactam
  • Pyrimidine
  • Alkyl phosphate
  • Imidazole
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility614.5 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.33 g/LALOGPS
logP-1.6ALOGPS
logP-6.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.71ChemAxon
pKa (Strongest Basic)4.92ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area232.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.94 m³·mol⁻¹ChemAxon
Polarizability34.31 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Pantothenate and CoA biosynthesisPW002463 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pantothenate and CoA biosynthesisec00770 Map00770
Purine metabolismec00230 Map00230
Sulfur metabolismec00920 Map00920
SMPDB Reactions
Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate → 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
Galabiosylceramide (d18:1/22:0) + Phosphoadenosine phosphosulfate → Galabiosylceramide-sulfate + Adenosine 3',5'-diphosphate
Phosphoadenosine phosphosulfate + reduced thioredoxin → Sulfite + oxidized thioredoxin + hydron + Adenosine 3',5'-diphosphate
KEGG Reactions
Adenosine 3',5'-diphosphate + waterAdenosine monophosphate + phosphate
water + Coenzyme AAdenosine 3',5'-diphosphate + Pantetheine 4'-phosphate + hydron
thioredoxin dithiol + Phosphoadenosine phosphosulfateAdenosine 3',5'-diphosphate + Sulfite + thioredoxin disulfide + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Thomas, D., Barbey, R., Surdin-Kerjan, Y. (1990). "Gene-enzyme relationship in the sulfate assimilation pathway of Saccharomyces cerevisiae. Study of the 3'-phosphoadenylylsulfate reductase structural gene." J Biol Chem 265:15518-15524.2203779
Synthesis Reference:Tsunako, Mitsutomo; Kotone, Akira. Preparation of nucleoside-2',5'- and 3',5'-diphosphoric acids. Jpn. Kokai Tokkyo Koho (1991), 13 pp.
External Links:
ResourceLink
CHEBI ID17985
HMDB IDHMDB00061
Pubchem Compound ID159296
Kegg IDC00054
ChemSpider ID140102
FOODB IDFDB021887
Wikipedia IDNot Available
BioCyc ID3-5-ADP

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Transfers the 4'-phosphopantetheine moiety from coenzyme A to a Ser of mitochondrial acyl-carrier-protein
Gene Name:
PPT2
Uniprot ID:
Q12036
Molecular weight:
19973.0
Reactions
CoA-(4'-phosphopantetheine) + apo-[acyl-carrier-protein] → adenosine 3',5'-bisphosphate + holo-[acyl-carrier-protein].
General function:
Involved in 3'(2'),5'-bisphosphate nucleotidase activity
Specific function:
Converts adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS) and 3'(2')-phosphoadenosine 5'- phosphate (PAP) to AMP. Regulates the flux of sulfur in the sulfur-activation pathway by converting PAPS to APS. Involved in salt tolerance. Confers resistance to lithium
Gene Name:
HAL2
Uniprot ID:
P32179
Molecular weight:
39148.89844
Reactions
Adenosine 3',5'-bisphosphate + H(2)O → adenosine 5'-phosphate + phosphate.
General function:
Involved in phosphoadenylyl-sulfate reductase (thioredoxin) activity
Specific function:
The NADP dependent reduction of PAPS into sulfite involves thioredoxin which probably plays the role of a thiol carrier
Gene Name:
MET16
Uniprot ID:
P18408
Molecular weight:
30380.09961
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 a 4'-phosphopantetheine moiety from coenzyme A to a serine residue of acceptor proteins, such as alpha-aminoadipate reductase. Necessary for alpha-aminoadipate reductase activity
Gene Name:
LYS5
Uniprot ID:
P50113
Molecular weight:
30682.90039
Reactions
CoA-[4'-phosphopantetheine] + apo-[acyl-carrier-protein] → adenosine 3',5'-bisphosphate + holo-[acyl-carrier-protein].