Basic information
- 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
- 347.06308442
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
Names & synonyms
adenosine 5'-monophosphate5'-adenylic acid61-19-8Adenosine monophosphateadenosine phosphatePhosphentasideadenosine 5'-phosphateAdenoviteCardiomoneLycedanPhosaden5'-AMP
Show more names
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 properties
- 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)
Physical DescriptionSolid
Stability/Shelf LifeFREE ACID & ITS SALTS ARE STABLE FOR LONG PERIODS IN DRY STATE; NEUTRAL SOLN ARE ALSO STABLE
Dissociation ConstantsPK1= 3.8; PK2= 6.2
Collision Cross Section
167.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
167 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
171.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
180.73 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
171.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
174.1 Ų [M-H]-
Safety & regulation
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
Status: Active Update: 10-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/22636
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
LOCAL ERYTHEMIA, SLIGHT FLUSHING, DIZZINESS, DIURESIS, & PALPITATION... ESPECIALLY WITH LARGE DOSES OF AQ SOLN. IN TREATMENT OF BURSITIS OR CHRONIC CALCIFIC TENDINITIS /DRUG OFTEN PRODUCES/ EXACERBATION OF SYMPTOMS AFTER 5TH TO 10TH DAY /ADVERSE EFFECT, IM (AS SODIUM SALT)/
DIARRHEA, DIZZINESS, & HEADACHE /SUBLINGUAL ADMIN/. ANAPHYLACTIC SHOCK... FOLLOWING USE OF GELATIN SOLN /IM ADMIN AS SODIUM SALT/. DYSPNEA & TIGHTNESS OF CHEST /ADVERSE EFFECT/
Non-Human Toxicity ExcerptsBIOSYNTHESIS OF FATTY ACIDS FROM [1-(14)C]-ACETATE BY CHICKEN LIVER SLICES IN VITRO WAS INHIBITED BY ADENOSINE-5'-MONOPHOSPHATE.
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
CIR ingredient: Adenosine Phosphate
IN BIOCHEMICAL RESEARCH
MEDICATION
Methods of Manufacturing
YEAST ADENYLIC ACID BY PRECIPITATION FROM YEAST NUCLEIC ACID. MUSCLE ADENYLIC ACID BY PRECIPITATION FROM TISSUES; BY HYDROLYSIS OF ATP WITH BARIUM HYDROXIDE...
COMMERCIAL PREPN BY ENZYMATIC PHOSPHORYLATION OF ADENOSINE. MONOGRAPH ON SYNTHESIS OF NUCLEOTIDES: CR PEFTIT, SYNTHETIC NUCLEOTIDES VOL 1 (VAN NOSTRAND-REINHOLD, NEW YORK, 1972) 252 PP.
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing Information
5'-Adenylic acid: ACTIVE
MONOPHOSPHORIC ESTER OF ADENOSINE, IE, NUCLEOTIDE CONTAINING ADENINE, D-RIBOSE & PHOSPHORIC ACID. ADENYLIC ACID IS CONSTITUENT OF MANY IMPORTANT COENZYMES.
Related reactions
16 records
Linked notes
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