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A3013

Adenosine 2′(3′)-monophosphate mixed isomers

Synonym(s):

Yeast adenylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H14N5O7P
CAS Number:
130-49-4
Molecular Weight:
347.22
NACRES:
NA.51
PubChem Substance ID:
24890716
UNSPSC Code:
41106305
EC Number:
204-990-7
MDL number:
MFCD00151215
eCl@ss:
32160414
Assay:
≥45% (Adenosine-3′-monophosphate, HPLC), ≥97% (Total Adenosine-3′-monophosphate; Adenosine-2′-monophosphate, HPLC), 10-55% ( Adenosine-2′-monophosphate, HPLC)
Biological source:
synthetic
Form:
powder
Solubility:
1 M NH4OH: 50 mg/mL, clear, colorless
Storage temp.:
−20°C
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biological source

synthetic

Quality Segment

200

assay

≥45% (Adenosine-3′-monophosphate, HPLC), ≥97% (Total Adenosine-3′-monophosphate; Adenosine-2′-monophosphate, HPLC), 10-55% ( Adenosine-2′-monophosphate, HPLC)

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]3O.Nc4ncnc5n(cnc45)[C@@H]6O[C@H](CO)[C@@H](O)[C@H]6OP(O)(O)=O

InChI

1S/2C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20;11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2*2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t2*4-,6-,7-,10-/m11/s1

InChI key

UQRXDDDXDPEXNS-VQFZJOCSSA-N

General description

Adenosine 3′-monophosphate (3′-AMP) and Adenosine 2′-monophosphate (2′-AMP) are metabolites produced from hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 2′-AMP and 3′-AMP inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors.

Application

Adenosine2′(3′)-monophosphate mixed isomers have been used as a standard to separate andquantify purines (adenine and guanine) and adenine ribonucleosidemonophosphates (2’-AMP and 3’-AMP) through isocratic high-performance liquidchromatography (HPLC). It has also been used to screen the multiplesugar-binding ATPase A (MsbA) transporter protein.

Other Notes

Do not confuse with adenosine 2′:3′-cyclic monophosphate

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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