P(1),P(4)-bis(5'-adenosyl) tetraphosphate (YMDB00590)

Identification

YMDB ID

YMDB00590

Name

P(1),P(4)-bis(5'-adenosyl) tetraphosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Diadenosine tetraphosphate, also known as appppa or (ppa)2, belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. Diadenosine tetraphosphate exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Diadenosine tetraphosphate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(ppA)2
5',5'''-Diadenosine tetraphosphate
A(5')p4(5')A
Adenosine 5'-tetraphosphate, 5'-ester with adenosine
adenosine-(5')-tetraphospho-(5')-adenosine
appppa
bis(5'-adenylyl) diphosphate
Diadenosine 5',5'''-P1,P4-tetraphosphate
P1,P4-Bis(5'-adenosyl) tetraphosphate
P1,P4-Di(adenosin-5'-yl)tetraphosphate
P1,P4-Diadenosine-5'-tetraphosphate
Bis(5'-adenylyl) diphosphoric acid
P1,P4-Bis(5'-adenosyl) tetraphosphoric acid
Diadenosine tetraphosphoric acid
Ap4a
P(1), P(4)-Diadenosine-5'tetraphosphate
Diadenosine 5',5'''-P(1),P(4)--tetraphosphate
Adenosine(5')tetraphospho(5')adenosine
Bis(5'-adenosyl)tetraphosphate
P1,P4-Bis(5'-adenosyl)tetraphosphoric acid
Diadenosine tetraphosphate
p(1),p(4)-Bis(5'-adenosyl) tetraphosphoric acid

CAS number

117137-55-0

Weight

Average: 836.387
Monoisotopic: 836.048264812

InChI Key

YOAHKNVSNCMZGQ-XPWFQUROSA-N

InChI

InChI=1S/C20H28N10O19P4/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1

IUPAC Name

[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid

Traditional IUPAC Name

appppa

Chemical Formula

C₂₀H₂₈N₁₀O₁₉P₄

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(5'->5')-dinucleotides

Sub Class

Not Available

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

(5'->5')-dinucleotide
Purine ribonucleoside polyphosphate
Purine nucleotide sugar
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Phosphoric acid ester
Imidolactam
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Amine
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

diadenosyl tetraphosphate (CHEBI:17422 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	-1.475	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	5.59 g/L	ALOGPS
logP	-0.71	ALOGPS
logP	-9.5	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.59	ChemAxon
pKa (Strongest Basic)	4.28	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	433.97 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	166.1 m³·mol⁻¹	ChemAxon
Polarizability	66.83 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Purine metabolism

ec00230

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0910200030-f62591a77764336369ca	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-f3c88b3e116ab3d6c1b4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-ed94ad304e91a867ff3b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-0700020090-f52e6941bbc750fe0e76	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900010000-dd233557a62d77a1406b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1915110000-741bdaae70092f502b8e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0100000090-0703d63dcb1429245411	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0300002090-89e8cc71cfb144d0f8b6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900101000-4b74d668fd588964dfd6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000090-bc4ce7d28b2ff5fc83e9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0201132090-cd2f5d95fa2a2c4f170a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-0410920120-5c5c92a5ab82e5e045d2	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17422
HMDB ID	HMDB01211
Pubchem Compound ID	21706
Kegg ID	C01260
ChemSpider ID	20402
FOODB ID	FDB022492
Wikipedia ID	Ap4A
BioCyc ID	ADENOSYL-P4

Enzymes

Protein Details

1. Protein APA1

General function:: Involved in ATP adenylyltransferase activity
Specific function:: Ap4A phosphorylase catabolizes Ap4N nucleotides (where N is A,C,G or U). Additionally this enzyme catalyzes the conversion of adenosine-5-phosphosulfate (AMPs) plus Pi to ADP plus sulfate, the exchange of NDP and phosphate and the synthesis of Ap4A from AMPs plus ATP
Gene Name:: APA1
Uniprot ID:: P16550
Molecular weight:: 36492.19922

Reactions

ADP + ATP → phosphate + P(1),P(4)-bis(5'-adenosyl) tetraphosphate.
ADP + sulfate → phosphate + adenylyl sulfate.
Adenylylsulfate + ATP → P(1),P(4)-bis(5'-adenosyl)tetraphosphate + sulfate.

Protein Details

2. Bis(5'-adenosyl)-triphosphatase

General function:: Involved in catalytic activity
Specific function:: Cleaves A-5'-PPP-5'A to yield AMP and ADP. Can cleave all dinucleoside polyphosphates, provided the phosphate chain contains at least 3 phosphates and that 1 of the 2 bases composing the nucleotide is a purine. Is most effective on dinucleoside triphosphates. Negatively regulates intracellular dinucleoside polyphosphate levels, which elevate following heat shock
Gene Name:: HNT2
Uniprot ID:: P49775
Molecular weight:: 23541.59961

Reactions

P(1)-P(3)-bis(5'-adenosyl) triphosphate + H(2)O → ADP + AMP.

Protein Details

3. 5',5'''-P-1,P-4-tetraphosphate phosphorylase 2

General function:: Involved in ATP adenylyltransferase activity
Specific function:: Sustains the catabolism of Np-4-N' nucleotides, rather than their synthesis
Gene Name:: APA2
Uniprot ID:: P22108
Molecular weight:: 36840.5

Reactions

ADP + ATP → phosphate + P(1),P(4)-bis(5'-adenosyl) tetraphosphate.

P(1),P(4)-bis(5'-adenosyl) tetraphosphate (YMDB00590)

Structure for #<Compound:0xb011a638>

Enzymes

Reactions

Reactions

Reactions