Adenosine 2'-phosphate (YMDB00564)

Identification

YMDB ID

YMDB00564

Name

Adenosine 2'-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Adenosine 2'-phosphate, also known as 2'-adenylic acid or AMP 2'-phosphate, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Adenosine 2'-phosphate is a strong basic compound (based on its pKa). Adenosine 2'-phosphate may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2'-Adenylic acid
adenosine 2'-monophosphate
Adenosine 2'-phosphate
Adenosine-2'-monophosphate
AMP 2'-phosphate
2'-Adenylate
Adenosine 2'-monophosphoric acid
ADENOSINE-2'-monophosphoric acid
AMP 2'-Phosphoric acid
Adenosine 2'-phosphoric acid
Adenylic acid
Dipotassium, adenosine phosphate
2'-AMP
2'-Adenosine monophosphate
Adenosine 5' phosphate
Disodium, adenosine phosphate
2' Adenosine monophosphate
Adenosine 2' phosphate
monoPhosphate, 2'-adenosine
Acid, 5'-adenylic
Phosphate dipotassium, adenosine
AMP
Acid, 2'-adenylic
Adenosine monophosphate
Adenosine 3'-phosphate
Adenosine phosphate disodium
5'-Phosphate, adenosine
Adenosine 5'-phosphate
Adenosine phosphate dipotassium
Phosphate disodium, adenosine
5' Adenylic acid
2' Adenylic acid
Phosphaden
Adenosine 3' phosphate
5'-Adenylic acid

CAS number

130-49-4

Weight

Average: 347.2212
Monoisotopic: 347.063084339

InChI Key

QDFHPFSBQFLLSW-KQYNXXCUSA-N

InChI

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

IUPAC Name

{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

Traditional IUPAC Name

adenosine 2'-phosphate

Chemical Formula

C₁₀H₁₄N₅O₇P

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OP(O)(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
N-glycosyl compound
Glycosyl compound
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Phosphoric acid ester
Imidolactam
Alkyl phosphate
Pyrimidine
N-substituted imidazole
Organic phosphoric acid derivative
Imidazole
Tetrahydrofuran
Azole
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine ribonucleoside 2'-monophosphate (CHEBI:28223 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	3.51 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-4.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	0.69	ChemAxon
pKa (Strongest Basic)	4.91	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	186.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.07 m³·mol⁻¹	ChemAxon
Polarizability	29.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

2',3'-cyclic AMP + water + hydron → Adenosine 2'-phosphate

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0942000000-5c237eed85b2a16f9799	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-91830941d3c4df3f32a3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-34129684d1ee8b1b1a37	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0032-5519000000-4032dc31817ae54a7a71	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900000000-13da8c715bedb0a7e501	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9400000000-edbf8ea8023cf964ef93	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C 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
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

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
Nasr, F., Filipowicz, W. (2000). "Characterization of the Saccharomyces cerevisiae cyclic nucleotide phosphodiesterase involved in the metabolism of ADP-ribose 1",2"-cyclic phosphate." Nucleic Acids Res 28:1676-1683.10734185

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	28223
HMDB ID	HMDB11617
Pubchem Compound ID	94136
Kegg ID	C00946
ChemSpider ID	84953
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	CPD-3705

Enzymes

Protein Details

1. 2',3'-cyclic-nucleotide 3'-phosphodiesterase

General function:: Involved in cyclic-nucleotide phosphodiesterase activity
Specific function:: Involved in the metabolism of ADP-ribose 1',2'-cyclic phosphate which is produced as a consequence of tRNA splicing
Gene Name:: CPD1
Uniprot ID:: P53314
Molecular weight:: 26731.40039

Reactions

Nucleoside 2',3'-cyclic phosphate + H(2)O → nucleoside 2'-phosphate.

Structure for #<Compound:0xa342a68c>

Enzymes

Reactions