Adenosine Monophosphate
Completing data — refresh the page later to see the latest
Basic information
- CAS
136920-07-5- Standard SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O- InChIKey
UDMBCSSLTHHNCD-KQYNXXCUSA-N- Molecular formula
- C10H14N5O7P
- Average molar mass
- 347.22 g/mol
- Monoisotopic mass
- 347.0630848
Overview
Adenosine 5'-monophosphate is a purine ribonucleoside 5'-monophosphate having adenine as the nucleobase. It has a role as a cofactor, a micronutrient, a nutraceutical, an EC 3.1.3.1 (alkaline phosphatase) inhibitor, an EC 3.1.3.11 (fructose-bisphosphatase) inhibitor, an adenosine A1 receptor agonist and a fundamental metabolite. It is a purine ribonucleoside 5'-monophosphate and an adenosine 5'-phosphate. It is a conjugate base of an adenosine 5'-monophosphate(1+). It is a conjugate acid of an adenosine 5'-monophosphate(2-).
Names & identifiers
- Preferred name
- Adenosine Monophosphate
- IUPAC
- [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- English name
- POLYADENYLIC ACID POTASSIUM SALT
- Molecular formula
- (C10H14N5O7P)x
- Molecular weight
- 347.22
Names & synonyms
adenosine 5'-monophosphate5'-adenylic acidAdenosine monophosphate61-19-8adenosine phosphateCardiomonePhosphentasideAdenoviteadenosine 5'-phosphateLycedanPhosaden5'-AMP
Show more names
5′-Adenylic acid, homopolymerPolyadenylicAcid,M.W.>100,000polyadenylic acid potassium salt mr ~7000000
adenylateMy-B-DenMyostonVitamin B8Adenyla-5mp5'-adenosine monophosphateFosfato de adenosina
Database identifiers
- CAS
136920-07-5、61-19-8- PubChem CID
- 6083
- DTXSID
DTXSID5022560- ChEMBL
CHEMBL752- ChEBI
CHEBI:16027- UNII
- 415SHH325A
- EC Number
- 200-500-0
- Nikkaji
- J4.814C
Properties
Computed structural propertiesFilling in
- XLogP
- -3.5
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 481
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetic ingredients (Adenosine Phosphate) -> CIR (Cosmetic Ingredient Review)
Skin conditioning
SpringerMaterials PropertiesAngular frequency
LogP-3.1
Color/Form
CRYSTALS FROM WATER + ACETONE
POWDER, NEEDLES FROM WATER & DIL ALC
Solubility
ALMOST INSOL IN COLD H2O /YEAST ADENYLIC ACID MONO-HCL/
READILY SOL IN BOILING WATER
SOL IN 10% HCL
INSOL IN ALCOHOL
10 mg/mL at 20 °C
Melting Point
196-200 °C
195 °C
Optical Rotation
SPECIFIC OPTICAL ROTATION: -26 DEG @ 20 °C/D (C= 2, 10% HCL); & -47.5 DEG @ 20 °C/D (C= 2, 2% NAOH)
MAX ABSORPTION (WATER, PH= 1.1): 255 NM (LOG E= 4.16); SPECIFIC OPTICAL ROTATION: -41.78 DEG @ 50 °C/D (WATER)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 97.7% (127 of 130) of all reports.
Not Classified
Aggregated GHS information provided per 130 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 5'-Adenylic acid
REACH registered substance: Adenosine phosphate (EC: 200-500-0)
Acetamide, 2,2',2'',2'''-(1,2-ethanediyldinitrilo)tetrakis-, N,N,N',N',N'',N'',N''',N'''-octa-C12-18-alkyl derivs.: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
adenosine 5 monophosphate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 5'-Adenylic acid: Environment tier I assessment
Hazard Classes and CategoriesNot Classified
Toxicology
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Natural Pollution SourcesNUCLEOTIDE; WIDELY DISTRIBUTED IN NATURE.
Human Toxicity Excerpts
Chemistry & industry
Pharmacology
Pharmacodynamics
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP is used as a dietary supplement to boost immune activity, and is also used as a substitute sweetener to aid in the maintenance of a low-calorie diet.
Mechanism of Action
Nucleotides such as Adenosine-5'-Monophosphate affect a number of immune functions, including the reversal of malnutrition and starvation-induced immunosuppression, the enhancement of T-cell maturation and function, the enhancement of natural killer cell activity, the improvement of delayed cutaneous hypersensitivity, helping resistance to such infectious agents as Staphylococcus aureus and Candida albicans, and finally the modulation of T-cell responses toward type 1 CD4 helper lymphocytes or Th1 cells. Studies have shown that mice fed a nucleotide-free diet have both impaired humoral and cellular immune responses. The addition of dietary nucleotides normalizes both types of responses. RNA, a delivery form of nucleotides, and ribonucleotides were used in these studies. The mechanism of the immune-enhancing activity of nucleic acids/nucleotides is not clear.
Absorption, Distribution and ExcretionAMP ADMIN TO RATS ORALLY WAS RECOVERED INTACT IN BLOOD. IT APPEARED RAPIDLY IN BLOOD (IN 15-30 MIN) & WAS ALSO RAPIDLY DISTRIBUTED, SINCE PLASMA CONCN WAS DECR BY FACTOR OF 5 IN 2 HR.
Tissue LocationsAll Tissues
Cellular LocationsCytoplasm
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)
Uses & manufacturing
Uses
Related reactions
16 records
Compound notes
Loading…