| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:48 -0700 |
| HMDB ID |
HMDB00045 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Adenosine monophosphate |
| Description |
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 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 5'-Adenosine monophosphate
- 5'-Adenylate
- 5'-Adenylic acid
- 5'-AMP
- Adenosine 5'-monophosphate
- Adenosine 5'-phosphate
- Adenosine 5'-phosphorate
- Adenosine 5'-phosphoric acid
- Adenosine phosphate
- Adenosine-5'-monophosphorate
- Adenosine-5'-monophosphoric acid
- Adenosine-5-monophosphorate
- Adenosine-5-monophosphoric acid
- Adenosine-monophosphate
- Adenosine-phosphate
- Adenovite
- Adenylate
- Adenylic acid
- AMP
- Cardiomone
- Lycedan
- Muscle adenylate
- Muscle adenylic acid
- My-B-Den
- My-beta-Den
- Phosaden
- Phosphaden
- Phosphentaside
|
| Chemical Formula |
C10H14N5O7P |
| Average Molecular Weight |
347.2212 |
| Monoisotopic Molecular Weight |
347.063084339 |
| IUPAC Name |
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid |
| Traditional IUPAC Name |
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid |
| CAS Registry Number |
61-19-8 |
| SMILES |
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O |
| InChI Identifier |
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 |
| InChI Key |
UDMBCSSLTHHNCD-KQYNXXCUSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Purine Nucleotides |
| Sub Class |
Purine Ribonucleotides |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
- Ribonucleotides(KEGG)
- adenosine 5'-phosphate(ChEBI)
- purine ribonucleoside 5'-monophosphate(ChEBI)
|
| Substituents |
- 1,2 Diol
- 1 Phosphoribosyl Imidazole
- Aminopyrimidine
- Glycosyl Compound
- Imidazole
- Imidazopyrimidine
- Monosaccharide Phosphate
- N Glycosyl Compound
- Organic Hypophosphite
- Organic Phosphite
- Oxolane
- Pentose Monosaccharide
- Phosphoric Acid Ester
- Purine
- Pyrimidine
- Saccharide
- Secondary Alcohol
|
| Direct Parent |
Purine Ribonucleoside Monophosphates |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Alanine and aspartate metabolism
- Component of Aminoacyl-tRNA biosynthesis
- Component of Arginine and proline metabolism
- Component of Biotin metabolism
- Component of Fatty acid metabolism
- Component of Glutamate metabolism
- Component of Glycine, serine and threonine metabolism
- Component of Histidine metabolism
- Component of Lysine biosynthesis
- Component of Methionine metabolism
- Component of Nitrogen metabolism
- Component of Phenylalanine, tyrosine and tryptophan biosynthesis
- Component of Porphyrin and chlorophyll metabolism
- Component of Propanoate metabolism
- Component of Purine metabolism
- Component of Pyrimidine metabolism
- Component of Pyruvate metabolism
- Component of Selenoamino acid metabolism
- Component of Sulfur metabolism
- Component of Thiamine metabolism
- Component of Tryptophan metabolism
- Component of Valine, leucine and isoleucine biosynthesis
|
| Application |
Not Available |
| Cellular locations |
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
- Endoplasmic reticulum
- Golgi apparatus
- Peroxisome
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| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
195 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
10 mg/mL at 20 °C |
BEILSTEIN |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
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| 1H NMR Spectrum |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| [1H,1H] 2D NMR Spectrum |
| [1H,13C] 2D NMR Spectrum |
|
| Biological Properties |
| Cellular Locations |
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
- Endoplasmic reticulum
- Golgi apparatus
- Peroxisome
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| Biofluid Locations |
- Blood
- Cellular Cytoplasm
- Cerebrospinal Fluid (CSF)
- Urine
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| Tissue Location |
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| Pathways |
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
5.1+/- 1.3 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
51.0 (10.0-92.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
14.0 +/- 3.0 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
6.2 +/- 3.1 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Cellular Cytoplasm |
Detected and Quantified |
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80.0 (71.0-89.0) uM |
Children (1-13 year old) |
Both |
Normal |
Not Available |
| Cellular Cytoplasm |
Detected and Quantified |
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23 uM |
Children (1-13 year old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
< 0.2 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Male |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB021806 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
5858  |
| KEGG Compound ID |
C00020  |
| BioCyc ID |
AMP  |
| BiGG ID |
33534  |
| Wikipedia Link |
Adenosine monophosphate  |
| NuGOwiki Link |
HMDB00045  |
| Metagene Link |
HMDB00045  |
| METLIN ID |
5111  |
| PubChem Compound |
6083  |
| PDB ID |
A  |
| ChEBI ID |
16027  |
| References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18.
Pubmed: 15882454
- BISHOP C, RANKINE DM, TALBOTT JH: The nucleotides in normal human blood. J Biol Chem. 1959 May;234(5):1233-7.
Pubmed: 13654353
- Lin CY, Ishida M: Elevation of cAMP levels in cerebrospinal fluid of patients with neonatal meningitis. Pediatrics. 1983 Jun;71(6):932-4.
Pubmed: 6304612
- Pagani R, Tabucchi A, Carlucci F, Leoncini R, Consolmagno E, Molinelli M, Valerio P: Some aspects of purine nucleotide metabolism in human lymphocytes before and after infection with HIV-1 virus: nucleotide content. Adv Exp Med Biol. 1991;309B:43-6.
Pubmed: 1781403
- Drezner MK, Neelon FA, Curtis HB, Lebovitz HE: Renal cyclic adenosine monophosphate: an accurate index of parathyroid function. Metabolism. 1976 Oct;25(10):1103-12.
Pubmed: 184364
- Aschenbach WG, Sakamoto K, Goodyear LJ: 5' adenosine monophosphate-activated protein kinase, metabolism and exercise. Sports Med. 2004;34(2):91-103.
Pubmed: 14965188
- Subramanian GM, Cronin PW, Poley G, Weinstein A, Stoughton SM, Zhong J, Ou Y, Zmuda JF, Osborn BL, Freimuth WW: A phase 1 study of PAmAb, a fully human monoclonal antibody against Bacillus anthracis protective antigen, in healthy volunteers. Clin Infect Dis. 2005 Jul 1;41(1):12-20. Epub 2005 May 24.
Pubmed: 15937757
- Aurbach GD: Genetic disorders involving parathyroid hormone and calcitonin. Birth Defects Orig Artic Ser. 1971 May;7(6):48-54.
Pubmed: 4155962
- Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7.
Pubmed: 6656991
- Post RM, Cramer H, Goodwin FK: Cyclic AMP in cerebrospinal fluid of manic and depressive patients. Psychol Med. 1977 Nov;7(4):599-605.
Pubmed: 201957
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| Enzymes |
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| Name: |
Glycogen phosphorylase, liver form
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| Reactions: |
- [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
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| Gene Name: |
PYGL |
| Uniprot ID: |
P06737  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Glycogen phosphorylase, brain form
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| Reactions: |
- [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
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| Gene Name: |
PYGB |
| Uniprot ID: |
P11216  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Biotin--protein ligase
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| Reactions: |
- ATP + biotin + apo-[acetyl-CoA:carbon-dioxide ligase (ADP-forming)] = AMP + diphosphate + [acetyl-CoA:carbon-dioxide ligase (ADP-forming)] [RN:R04562]
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| Gene Name: |
HLCS |
| Uniprot ID: |
P50747  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Glycyl-tRNA synthetase
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| Reactions: |
- ATP + glycine + tRNAGly = AMP + diphosphate + glycyl-tRNAGly [RN:R03654]
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| Gene Name: |
GARS |
| Uniprot ID: |
P41250  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Asparagine synthetase [glutamine-hydrolyzing]
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| Reactions: |
- (1) ATP + L-aspartate + L-glutamine + H2O = AMP + diphosphate + L-asparagine + L-glutamate [RN:R00578]
- (2) (1a) L-glutamine + H2O = L-glutamate + NH3 [RN:R00256]
- (3) (1b) ATP + L-aspartate + NH3 = AMP + diphosphate + L-asparagine [RN:R00483]
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| Gene Name: |
ASNS |
| Uniprot ID: |
P08243  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Adenylosuccinate lyase
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| Reactions: |
- (1) N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP [RN:R01083]
- (2) (S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxamido]succinate = fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide [RN:R04559]
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| Gene Name: |
ADSL |
| Uniprot ID: |
P30566  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA ligase 4
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| Reactions: |
- ATP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = AMP + diphosphate + (deoxyribonucleotide)n+m [RN:R00381]
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| Gene Name: |
LIG4 |
| Uniprot ID: |
P49917  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA ligase 3
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| Reactions: |
- ATP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = AMP + diphosphate + (deoxyribonucleotide)n+m [RN:R00381]
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| Gene Name: |
LIG3 |
| Uniprot ID: |
P49916  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lysyl-tRNA synthetase
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| Reactions: |
- ATP + L-lysine + tRNALys = AMP + diphosphate + L-lysyl-tRNALys [RN:R03658]
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| Gene Name: |
KARS |
| Uniprot ID: |
Q15046  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Valyl-tRNA synthetase
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| Reactions: |
- ATP + L-valine + tRNAVal = AMP + diphosphate + L-valyl-tRNAVal [RN:R03665]
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| Gene Name: |
VARS |
| Uniprot ID: |
P26640  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Argininosuccinate synthase
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| Reactions: |
- ATP + L-citrulline + L-aspartate = AMP + diphosphate + 2-(Nomega-L-arginino)succinate [RN:R01954]
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| Gene Name: |
ASS1 |
| Uniprot ID: |
P00966  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
DNA ligase 1
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| Reactions: |
- ATP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = AMP + diphosphate + (deoxyribonucleotide)n+m [RN:R00381]
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| Gene Name: |
LIG1 |
| Uniprot ID: |
P18858  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Bile acyl-CoA synthetase
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| Reactions: |
- (1) ATP + cholate + CoA = AMP + diphosphate + choloyl-CoA [RN:R02794]
- (2) ATP + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate + CoA = AMP + diphosphate + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA [RN:R04580]
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| Gene Name: |
SLC27A5 |
| Uniprot ID: |
Q9Y2P5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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