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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 PHOSPHATE

SMILES

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

InChI

InChIKey=UDMBCSSLTHHNCD-KQYNXXCUSA-N
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/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: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12614440 | https://clinicaltrials.gov/ct2/show/NCT00179010

Adenosine monophosphate (AMP) is a nucleotide, consisting of a phosphate group, the sugar ribose, and the nucleobase adenine. AMP is an activator of several enzymes in the tissues. In the glycolytic pathway, the enzyme phosphofructokinase is inhibited by ATP but the inhibition is reversed by AMP, the deciding factor for the reaction being the ratio between ATP and AMP. In medicine, AMP is used mainly as an alternative to adenosine for treatment of ischemia and as a tool compound to measure hyperresponsiveness of airways.

Approval Year

1949
71
Targets

Targets

Primary TargetPharmacologyConditionPotency
5'-nucleotidase
7
Target ID: P21589
Gene ID: 4907.0
Gene Symbol: NT5E
Target Organism: Homo sapiens (Human)
Substrate
661
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Not Provided
511
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OATP1B1
1079

OATP1B3
961
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OATP1B1
1095
 yes [Inhibition 10 uM]
OATP1B3
970
 yes [Inhibition 10 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
BLD Pharm
BD01225746
http://www.bldpharm.com/products/26763-19-9.html
BLD Pharm
BD756296
http://www.bldpharm.com/products/134296-35-8.html
PubChem
66927421
https://pubchem.ncbi.nlm.nih.gov/compound/66927421
PubMed

PubMed

TitleDatePubMed
Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal.
2001-03-02
Expression of type I adenylyl cyclase in intrinsic pathways of the hippocampal formation of the macaque (Macaca nemestrina).
2001-02-23
GH mRNA levels are elevated by forskolin but not GH releasing hormone in GHRH receptor-expressing MtT/S somatotroph cell line.
2001-02-14
Prostaglandin E2 and vasoactive intestinal peptide increase vascular endothelial cell growth factor mRNAs in lung cancer cells.
2001-02-13
Does the developmental neurotoxicity of chlorpyrifos involve glial targets? Macromolecule synthesis, adenylyl cyclase signaling, nuclear transcription factors, and formation of reactive oxygen in C6 glioma cells.
2001-02-09
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.
2001-02-02
C-type natriuretic peptide has a negative inotropic effect on cardiac myocytes.
2001-02-02
Structural analysis of adenylate cyclases from Trypanosoma brucei in their monomeric state.
2001-02-01
Brief treatments with forskolin enhance s-phase entry in balance epithelia from the ears of rats.
2001-02-01
Functional and molecular characterization of receptor subtypes mediating coronary microvascular dilation to adenosine.
2001-02
The phosphodiesterase inhibitors pentoxifylline and rolipram suppress macrophage activation and nitric oxide production in vitro and in vivo.
2001-02
ST14A cells have properties of a medium-size spiny neuron.
2001-02
Maintaining methylation activities during salt stress. The involvement of adenosine kinase.
2001-02
Characterization of a G protein-coupled receptor for nicotinic acid.
2001-02
Partial agonist clonidine mediates alpha(2)-AR subtypes specific regulation of cAMP accumulation in adenylyl cyclase II transfected DDT1-MF2 cells.
2001-02
Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex.
2001-02
Peptones stimulate intestinal cholecystokinin gene transcription via cyclic adenosine monophosphate response element-binding factors.
2001-02
Regulation of phosphate uptake in primary cultured rabbit renal proximal tubule cells by glucocorticoids: evidence for nongenomic as well as genomic mechanisms.
2001-02
Autoradiographic localization of specific binding of meiosis-activating sterol to cumulus-oocyte complexes from marmoset, cow, and mouse.
2001-02
Adrenomedullin expression and growth inhibitory effects in distinct pulmonary artery smooth muscle cell subpopulations.
2001-02
Regulation of G protein-coupled receptor-adenylyl cyclase responsiveness in human airway smooth muscle by exogenous and autocrine adenosine.
2001-02
PTH and PTH-related peptide enhance steroid secretion from human adrenocortical cells.
2001-02
Beta,gamma-methylene ATP-induced cAMP formation in C6Bu-1 cells: involvement of local metabolism and subsequent stimulation of adenosine A2B receptor.
2001-02
C2-ceramide and reactive oxygen species inhibit pituitary adenylate cyclase activating polypeptide (PACAP)-induced cyclic-AMP-dependent signalling pathway.
2001-02
Construction of gene therapy vectors targeting thyroid cells: enhancement of activity and specificity with histone deacetylase inhibitors and agents modulating the cyclic adenosine 3',5'-monophosphate pathway and demonstration of activity in follicular and anaplastic thyroid carcinoma cells.
2001-02
Orexin A stimulates cortisol secretion from human adrenocortical cells through activation of the adenylate cyclase-dependent signaling cascade.
2001-02
Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes.
2001-02
Cerebroprotective action of a Na+/Ca2+ channel blocker NS-7. I. Effect on the cerebral infarction and edema at the acute stage of permanent middle cerebral artery occlusion in rats.
2001-01-26
Estrogen modulates norepinephrine-induced accumulation of adenosine cyclic monophosphate in a subpopulation of immortalized luteinizing hormone-releasing hormone secreting neurons from the mouse hypothalamus.
2001-01-26
Hypothalamic orexin-A binding sites are downregulated by chronic nicotine treatment in the rat.
2001-01-26
Expression and purification of polyhistidine-tagged firefly luciferase in insect cells--a potential alternative for process scale-up.
2001-01-23
Adenosine receptor subtypes modulate two major functional pathways for hippocampal serotonin release.
2001-01-15
Effects of the nitric oxide/cGMP system compared with the cAMP system on airway mucus secretion in the rat.
2001-01-12
Localization and mechanisms of action of cannabinoid receptors at the glutamatergic synapses of the mouse nucleus accumbens.
2001-01-01
Role of stimulatory guanine nucleotide binding protein (GSalpha) in proliferation of PC-3M prostate cancer cells.
2001-01-01
Chemical coding of intrinsic and extrinsic nerves in the guinea pig gallbladder: distributions of PACAP and orphanin FQ.
2001-01-01
Pituitary adenylate cyclase activating peptide (PACAP) in the enteropancreatic innervation.
2001-01-01
Involvement of endogenous PACAP expression in the activity-dependent survival of mouse cerebellar granule cells.
2001-01
G protein and cAMP-dependent protein kinase mediate amyloid beta-peptide inhibition of neuronal glucose uptake.
2001-01
Nitrogen-dependent accumulation of cytokinins in root and the translocation to leaf: implication of cytokinin species that induces gene expression of maize response regulator.
2001-01
Differential coupling of the human P2Y(11) receptor to phospholipase C and adenylyl cyclase.
2001-01
Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells.
2001-01
Peptidergic modulation of an insect Na(+) current: role of protein kinase A and protein kinase C.
2001-01
cAMP-dependent presynaptic regulation of spontaneous glycinergic IPSCs in mechanically dissociated rat spinal cord neurons.
2001-01
Effects of prostaglandin E2 and cAMP elevating drugs on GM-CSF release by cultured human airway smooth muscle cells. Relevance to asthma therapy.
2001-01
Regulation of TNF-alpha-induced eotaxin release from cultured human airway smooth muscle cells by beta2-agonists and corticosteroids.
2001-01
Extracellular ATP formation on vascular endothelial cells is mediated by ecto-nucleotide kinase activities via phosphotransfer reactions.
2001-01
A novel transverse push-pull microprobe: in vitro characterization and in vivo demonstration of the enzymatic production of adenosine in the spinal cord dorsal horn.
2001-01
Tubulin stimulates adenylyl cyclase activity in C6 glioma cells by bypassing the beta-adrenergic receptor: a potential mechanism of G protein activation.
2001-01
AgRP(83-132) acts as an inverse agonist on the human-melanocortin-4 receptor.
2001-01
Patents

Patents

JP2000041695A
4
JP2000262296A
4
JP2001288043A
4
JP2001288048A
4
JP2002338467A
4
JP2002520061A
4
JP2003250555A
4
JP2005104886A
4
JP2006193445A
4
JP2006518843A
4
JP2008532605A
4
JP2009060809A
4
JP2009523584A
4
JPH01214352A
4
JPH03120438A
4
JPH0343A
4
JPH0368564A
4
JPH04164254A
4
JPH04305528A
4
JPH05252899A
4
JPH0769896A
4
JPH09285267A
4
JPH1082757A
4
JPH11244296A
4
JPS05765181A
4
JPS05820197A
4
JPS0678594A
4
JPS56115800A
4
JPS5711998A
4
JPS5711999A
4
JPS57166992A
4
JPS572695A
4
JPS59106296A
6
JPS59109153A
4
JPS61260895A
8
JPS62286904A
4
JPS6311848A
4

Sample Use Guides

In Vivo Use Guide
In clinical studies for treatment of Ichemia, adenosine monophosphate is administered by intraaterial infusion of AMP at 3 different doses for 15 minutes each (at equimolar doses as adenosine). As a tool to measure hyperresponsiveness of airways, AMP was administered internasally.
Route of Administration: Other
In Vitro Use Guide
To measure activity of 5’-nucleotidase, lymphocytes from peripheral blood were incubated with [G-3H]adenosine 5'-monophosphate. Aliquots were removed after 0, 15, 30, and 60 min of incubation without shaking. The cells were washed twice with phosphate buffered saline. The cells were dissolved in 7 ml of Aquasol, and the radioactivity was determined in a scintillation counter.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:46:15 GMT 2025
Edited
by admin
on Wed Apr 02 09:46:15 GMT 2025
Record UNII
415SHH325A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
5'-ADENYLIC ACID
FCC   MI   USP-RS  
Preferred Name English
ADENOSINE PHOSPHATE
HSDB   INCI   INN   MART.   USAN   VANDF   WHO-DD  
INN   USAN   INCI  
Official Name English
A 5MP
Code English
adenosine phosphate [INN]
Common Name English
NSC-20264
Code English
ADENOSINE 5'-(DIHYDROGEN PHOSPHATE).
Common Name English
Adenosine phosphate [WHO-DD]
Common Name English
ADENOSINE 5'-MONOPHOSPHATE
Systematic Name English
5'-ADENYLIC ACID [USP-RS]
Common Name English
A-5MP
Code English
ADENOSINE PHOSPHATE [MART.]
Common Name English
ADENOSINE PHOSPHATE [USAN]
Common Name English
ADENOSINE PHOSPHATE [VANDF]
Common Name English
ADENOSINE PHOSPHATE [HSDB]
Common Name English
ADENOSINE 5'-MONOPHOSPHORIC ACID
Common Name English
AMP
Common Name English
5'-ADENYLIC ACID [MI]
Common Name English
5'-ADENYLIC ACID [FCC]
Common Name English
ADENYL
Brand Name English
ADENOSINE MONOPHOSPHATE
Systematic Name English
Classification Tree Code System Code
DSLD 3633 (Number of products:8)
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
NCI_THESAURUS C709
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
CFR 21 CFR 216.24
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
Code System Code Type Description
HSDB
3281
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID5022560
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
RXCUI
309
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
ADENOSINE MONOPHOSPHATE
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
NSC
20264
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
CAS
53624-78-5
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
SUPERSEDED
NCI_THESAURUS
C83606
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-500-0
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
GRAS Notification (GRN No.)
144
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
PUBCHEM
6083
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
MERCK INDEX
m1416
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY Merck Index
FDA UNII
415SHH325A
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
MESH
D000249
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
CHEBI
16027
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
CAS
61-19-8
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL752
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
DAILYMED
415SHH325A
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
RS_ITEM_NUM
1012178
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
DRUG CENTRAL
92
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
SMS_ID
100000087682
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
EVMPD
SUB05267MIG
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
INN
335
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
DRUG BANK
DB00131
Created by admin on Wed Apr 02 09:46:15 GMT 2025 , Edited by admin on Wed Apr 02 09:46:15 GMT 2025
PRIMARY
Related Record Type Details
Structure of ADENOSINE PHOSPHATE DIPOTASSIUM
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Structure of ADENOSINE PHOSPHATE MONOSODIUM
SALT/SOLVATE -> PARENT
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SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ADENOSINE PHOSPHATE
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