Common NameAmp
DescriptionAdenosine 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 can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.
Structure
Molecular FormulaC10H14N5O7P
Average Mass347.22120
Monoisotopic Mass347.06308
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number61-19-8
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]1O
InChI IdentifierInChI=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
InChI KeyUDMBCSSLTHHNCD-KQYNXXCUSA-N
CHEBI IDCHEBI:456215
HMDB IDHMDB0000045
Pathways
NameSMPDB/PathBank
Purine metabolism
Nitrogen metabolism
Glycine, serine and threonine metabolism
Alanine, aspartate and glutamate metabolism
Selenocompound metabolism
Arginine and proline metabolism
Phenylalanine metabolism
pentose phosphate pathway
Pyruvate metabolism
Nicotinate and nicotinamide metabolism
Propanoate metabolism
Citrullinemia Type I
Carbamoyl Phosphate Synthetase Deficiency
Argininosuccinic Aciduria
Phenylalanine and Tyrosine Metabolism
Cysteine Metabolism
Transcription/Translation
Pantothenate and CoA Biosynthesis
Methionine Metabolism
Histidine metabolism
Fatty acid Metabolism
Urea Cycle
Aspartate Metabolism
Riboflavin Metabolism
Glutamate Metabolism
Butyrate Metabolism
Thiamine Metabolism
2-Hydroxyglutric Aciduria (D And L Form)
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Canavan Disease
Cystathionine Beta-Synthase Deficiency
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Ethylmalonic Encephalopathy
Glutaric Aciduria Type I
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)
Histidinemia
Hypoacetylaspartia
Leigh Syndrome
Malonic Aciduria
Methylmalonic Aciduria Due to Cobalamin-Related Disorders
Molybdenum Cofactor Deficiency
Ornithine Transcarbamylase Deficiency (OTC Deficiency)
Phenylketonuria
Prolidase Deficiency (PD)
Prolinemia Type II
Purine Nucleoside Phosphorylase Deficiency
Pyruvate Dehydrogenase Complex Deficiency
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Methionine Adenosyltransferase Deficiency
Glycine N-methyltransferase Deficiency
Non Ketotic Hyperglycinemia
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)
Dimethylglycine Dehydrogenase Deficiency
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Sarcosinemia
Azithromycin Action Pathway
Clarithromycin Action Pathway
Clindamycin Action Pathway
Erythromycin Action Pathway
Roxithromycin Action Pathway
Telithromycin Action Pathway
Amikacin Action Pathway
Gentamicin Action Pathway
Kanamycin Action Pathway
Neomycin Action Pathway
Netilmicin Action Pathway
Spectinomycin Action Pathway
Streptomycin Action Pathway
Clomocycline Action Pathway
Demeclocycline Action Pathway
Doxycycline Action Pathway
Minocycline Action Pathway
Oxytetracycline Action Pathway
Tetracycline Action Pathway
Lymecycline Action Pathway
Lactic Acidemia
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)
Hyperinsulinism-Hyperammonemia Syndrome
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Hypermethioninemia
Pyruvate Carboxylase Deficiency
Primary Hyperoxaluria Type I
Argininemia
Hyperprolinemia Type II
Hyperprolinemia Type I
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)
Ornithine Aminotransferase Deficiency (OAT Deficiency)
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)
Tyrosinemia Type 3 (TYRO3)
Homocarnosinosis
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Disulfiram Action Pathway
Thioguanine Action Pathway
Ethanol Degradation
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
Beta-mercaptolactate-cysteine disulfiduria
Malonyl-coa decarboxylase deficiency
Creatine deficiency, guanidinoacetate methyltransferase deficiency
Hyperornithinemia with gyrate atrophy (HOGA)
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]
L-arginine:glycine amidinotransferase deficiency
Xanthinuria type I
Xanthinuria type II
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
Carnitine palmitoyl transferase deficiency (I)
Long chain acyl-CoA dehydrogenase deficiency (LCAD)
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)
Carnitine palmitoyl transferase deficiency (II)
Medium chain acyl-coa dehydrogenase deficiency (MCAD)
Trifunctional protein deficiency
Primary hyperoxaluria II, PH2
Pyruvate kinase deficiency
Succinic semialdehyde dehydrogenase deficiency
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type
Mercaptopurine Metabolism Pathway
Valproic Acid Metabolism Pathway
Tobramycin Action Pathway
Tigecycline Action Pathway
Arbekacin Action Pathway
Paromomycin Action Pathway
3-Phosphoglycerate dehydrogenase deficiency
Cystinosis, ocular nonnephropathic
Rolitetracycline Action Pathway
Methacycline Action Pathway
Lincomycin Action Pathway
Chloramphenicol Action Pathway
Troleandomycin Action Pathway
Josamycin Action Pathway
Abacavir Action Pathway
Delavirdine Action Pathway
Didanosine Action Pathway
Efavirenz Action Pathway
Emtricitabine Action Pathway
Lamivudine Action Pathway
Nevirapine Action Pathway
Rilpivirine Action Pathway
Stavudine Action Pathway
Zalcitabine Action Pathway
Zidovudine Action Pathway
Acylcarnitine 3-Hydroxydecanoylcarnitine
Acylcarnitine (7Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-7,9,12,15,18,21-hexaenoylcarnitine
Acylcarnitine Pentacosanoylcarnitine
Acylcarnitine Hexacosanoylcarnitine
Acylcarnitine (17Z)-Hexacos-17-enoylcarnitine
Acylcarnitine (13Z,16Z)-Hexacosa-13,16-dienoylcarnitine
Acylcarnitine Heptacosanoylcarnitine
Acylcarnitine Octacosanoylcarnitine
Acylcarnitine Nonacosanoylcarnitine
Acylcarnitine (2S,3R)-3-Hydroxy-2-methylbutanoylcarnitine
StateNot Available
Water Solubility3.31e+00 g/l
logP-3.13
logS-2.02
pKa (Strongest Acidic)1.23
pKa (Strongest Basic)4.97
Hydrogen Acceptor Count10
Hydrogen Donor Count5
Polar Surface Area186.07 Ų
Rotatable Bond Count4
Physiological Charge-2
Formal Charge0
Refractivity74.07 m³·mol⁻¹
Polarizability29.65

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