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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N5O7P
Molecular Weight 347.2212
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADENOSINE 2'-MONOPHOSPHATE

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3OP(O)(O)=O

InChI

InChIKey=QDFHPFSBQFLLSW-KQYNXXCUSA-N
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

HIDE SMILES / InChI

Molecular Formula C10H14N5O7P
Molecular Weight 347.2212
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21270135 | https://www.ncbi.nlm.nih.gov/pubmed/22738238 | https://www.ncbi.nlm.nih.gov/pubmed/23759508

Adenosine 2'-monophosphate (2’-AMP) is adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'- position. Exogenous 2’-AMP is rapidly converted to adenosine in vitro and in vivo. In vitro 2’-AMP alter vascular smooth muscle cell, endothelial cell, and epithelial cell proliferation via adenosine receptors activation. In vitro 2’-AMP dose-dependently and profoundly reduce mean arterial blood pressure, heart rate, total peripheral (TPR), mesenteric vascular (MVR) resistances with efficacies and potencies equal to or greater than those for adenosine. Adenosine 2'-monophosphate has been used in the synthesis of a novel photoaffinity label for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase. Adenosine 2'-monophosphate also can be used as a tool for studying adenosine-based cell regulation.

Originator

Sources: Journal of Biological Chemistry (1951), 188, 665-76.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.49 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Reaction of neuronal nitric-oxide synthase with 2,6-dichloroindolphenol and cytochrome c3+: influence of the electron acceptor and binding of Ca2+-activated calmodulin on the kinetic mechanism.
2001 Apr 17
Unexpected binding mode for 2'-phosphoadenosine-based nucleotide inhibitors in complex with human angiogenin revealed by heteronuclear NMR spectroscopy.
2003 Sep 30
Patents

Sample Use Guides

i.v. infusion as a dose of 0.03 mmol/kg, 0.1 and 0.3 mmol/kg per minute for 40 minutes
Route of Administration: Intravenous
PGVSMCs and GMCs were plated at an initial density of 5000 cells/culture in Dulbecco’s modified Eagle’s medium Nutrient Mixture F-12 (DMEM/F12) containing 2.5% fetal calf serum and were allowed to attach and proliferate overnight. The next day, cells were growth-arrested in DMEM/F12 containing 0.25% albumin for 24 h to synchronize cells. Then DMEM/F12 containing 2.5% fetal calf serum (along with the various treatments) was added to stimulate cell proliferation. Treatments (Adenosine 2'-monophosphate 30 mkM) were administered daily, and after 4 days the cell number was determined by counting cells with a Coulter counter.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:49:54 GMT 2023
Edited
by admin
on Sat Dec 16 08:49:54 GMT 2023
Record UNII
W907528R6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADENOSINE 2'-MONOPHOSPHATE
Systematic Name English
ADENOSINE 2'-PHOSPHATE
Systematic Name English
2'-ADENYLIC ACID
Systematic Name English
ADENOSINE 2'-(DIHYDROGEN PHOSPHATE)
Systematic Name English
Code System Code Type Description
CHEBI
77740
Created by admin on Sat Dec 16 08:49:54 GMT 2023 , Edited by admin on Sat Dec 16 08:49:54 GMT 2023
PRIMARY
PUBCHEM
94136
Created by admin on Sat Dec 16 08:49:54 GMT 2023 , Edited by admin on Sat Dec 16 08:49:54 GMT 2023
PRIMARY
FDA UNII
W907528R6O
Created by admin on Sat Dec 16 08:49:54 GMT 2023 , Edited by admin on Sat Dec 16 08:49:54 GMT 2023
PRIMARY
CHEBI
28223
Created by admin on Sat Dec 16 08:49:54 GMT 2023 , Edited by admin on Sat Dec 16 08:49:54 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-990-7
Created by admin on Sat Dec 16 08:49:54 GMT 2023 , Edited by admin on Sat Dec 16 08:49:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID00926554
Created by admin on Sat Dec 16 08:49:54 GMT 2023 , Edited by admin on Sat Dec 16 08:49:54 GMT 2023
PRIMARY
CAS
130-49-4
Created by admin on Sat Dec 16 08:49:54 GMT 2023 , Edited by admin on Sat Dec 16 08:49:54 GMT 2023
PRIMARY