Metabolite page

Showing information for HMDB0000045 ("adenosine 5'-monophosphate", 'AMP', 'adenosine-5-phosphate')

Metabolite information
HMDB ID	HMDB0000045
Synonyms	2' Adenosine monophosphate 2' Adenylic acid 2'-AMP 2'-Adenosine monophosphate 2'-Adenylic acid 5' Adenylic acid 5'-AMP 5'-Adenosine monophosphate 5'-Adenosine monophosphoric acid 5'-Adenylate 5'-Adenylic acid 5'-O-Phosphonoadenosine 5'-Phosphate, adenosine AMP Acid, 2'-adenylic Acid, 5'-adenylic Adenosine 2' phosphate Adenosine 2'-phosphate Adenosine 3' phosphate Adenosine 3'-phosphate Adenosine 5' phosphate Adenosine 5'-[dihydrogen phosphate] Adenosine 5'-[dihydrogen phosphoric acid] Adenosine 5'-monophosphate Adenosine 5'-monophosphoric acid Adenosine 5'-phosphate Adenosine 5'-phosphorate Adenosine 5'-phosphoric acid Adenosine monophosphoric acid Adenosine phosphate Adenosine phosphate dipotassium Adenosine phosphate disodium Adenosine phosphoric acid Adenosine-5'-monophosphate Adenosine-5'-monophosphorate Adenosine-5'-monophosphoric acid Adenosine-5'p Adenosine-5-monophosphorate Adenosine-5-monophosphoric acid Adenosine-monophosphate Adenosine-phosphate Adenosini phosphas Adenovite Adenylate Adenylic acid Ado5'p Cardiomone Cell nucleus Csf Cytoplasma Dipotassium, adenosine phosphate Disodium, adenosine phosphate Ee Er Extracellular region Faecal Faeces Fecal Golgi apparatus Golgi complex Golgi ribbon Lycedan Monophosphate, 2'-adenosine Muscle adenylate Muscle adenylic acid My-b-den My-beta-den Nucleic PAdo Peroxisomal Peroxisome vesicle Phosaden Phosphaden Phosphate d'adenosine Phosphate dipotassium, adenosine Phosphate disodium, adenosine Phosphentaside Phosphoric acid d'adenosine Stool [epema syndrome] fosfato De adenosina pA
Chemical formula	C10H14N5O7P
IUPAC name	{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
CAS registry number	61-19-8
Monisotopic molecular weight	347.063084339
Chemical taxonomy
Super class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub class	Purine ribonucleotides
Biological properties
Pahtways	2-Hydroxyglutric Aciduria [D And L Form] 3-Phosphoglycerate dehydrogenase deficiency 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency AICA-Ribosiduria Abacavir Action Pathway Adenine phosphoribosyltransferase deficiency [APRT] Adenosine Deaminase Deficiency Adenylosuccinate Lyase Deficiency Alanine Metabolism Amikacin Action Pathway Ammonia Recycling Arbekacin Action Pathway Arginine and Proline Metabolism Arginine: Glycine Amidinotransferase Deficiency [AGAT Deficiency] Argininemia Argininosuccinic Aciduria Aspartate Metabolism Azathioprine Action Pathway Azithromycin Action Pathway Beta-mercaptolactate-cysteine disulfiduria Butyrate Metabolism Canavan Disease Carbamoyl Phosphate Synthetase Deficiency Carnitine palmitoyl transferase deficiency [II] Carnitine palmitoyl transferase deficiency [I] Chloramphenicol Action Pathway Citrullinemia Type I Clarithromycin Action Pathway Clindamycin Action Pathway Clomocycline Action Pathway Creatine deficiency, guanidinoacetate methyltransferase deficiency Cystathionine Beta-Synthase Deficiency Cysteine Metabolism Cystinosis, ocular nonnephropathic Delavirdine Action Pathway Demeclocycline Action Pathway Didanosine Action Pathway Dihydropyrimidine Dehydrogenase Deficiency [DHPD] Dimethylglycine Dehydrogenase Deficiency Dimethylglycine Dehydrogenase Deficiency Disulfiram Action Pathway Doxycycline Action Pathway Efavirenz Action Pathway Emtricitabine Action Pathway Erythromycin Action Pathway Ethanol Degradation Ethylmalonic Encephalopathy Fatty acid Metabolism Gentamicin Action Pathway Glucose-6-phosphate dehydrogenase deficiency Glutamate Metabolism Glutaric Aciduria Type I Glycine N-methyltransferase Deficiency Glycine and Serine Metabolism Gout or Kelley-Seegmiller Syndrome Guanidinoacetate Methyltransferase Deficiency [GAMT Deficiency] Histidine Metabolism Histidinemia Homocarnosinosis Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type Hyperglycinemia, non-ketotic Hyperinsulinism-Hyperammonemia Syndrome Hypermethioninemia Hyperornithinemia with gyrate atrophy [HOGA] Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome] Hyperprolinemia Type I Hyperprolinemia Type II Hypoacetylaspartia Josamycin Action Pathway Kanamycin Action Pathway L-arginine:glycine amidinotransferase deficiency Lactic Acidemia Lamivudine Action Pathway Leigh Syndrome Lesch-Nyhan Syndrome [LNS] Lincomycin Action Pathway Long chain acyl-CoA dehydrogenase deficiency [LCAD] Lymecycline Action Pathway Malonic Aciduria Malonyl-coa decarboxylase deficiency Medium chain acyl-coa dehydrogenase deficiency [MCAD] Mercaptopurine Action Pathway Mercaptopurine Metabolism Pathway Methacycline Action Pathway Methionine Adenosyltransferase Deficiency Methionine Metabolism Methylenetetrahydrofolate Reductase Deficiency [MTHFRD] Methylmalonic Aciduria Due to Cobalamin-Related Disorders Minocycline Action Pathway Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids Mitochondrial DNA depletion syndrome Molybdenum Cofactor Deficiency Myoadenylate deaminase deficiency Neomycin Action Pathway Netilmicin Action Pathway Nevirapine Action Pathway Nicotinate and Nicotinamide Metabolism Non Ketotic Hyperglycinemia Ornithine Aminotransferase Deficiency [OAT Deficiency] Ornithine Transcarbamylase Deficiency [OTC Deficiency] Oxytetracycline Action Pathway Pantothenate and CoA Biosynthesis Paromomycin Action Pathway Pentose Phosphate Pathway Phenylacetate Metabolism Phenylalanine and Tyrosine Metabolism Phenylketonuria Primary Hyperoxaluria Type I Primary hyperoxaluria II, PH2 Prolidase Deficiency [PD] Prolinemia Type II Propanoate Metabolism Purine Metabolism Purine Nucleoside Phosphorylase Deficiency Pyruvate Carboxylase Deficiency Pyruvate Decarboxylase E1 Component Deficiency [PDHE1 Deficiency] Pyruvate Dehydrogenase Complex Deficiency Pyruvate Metabolism Pyruvate kinase deficiency Riboflavin Metabolism Ribose-5-phosphate isomerase deficiency Rilpivirine Action Pathway Rolitetracycline Action Pathway Roxithromycin Action Pathway S-Adenosylhomocysteine [SAH] Hydrolase Deficiency Sarcosinemia Selenoamino Acid Metabolism Short Chain Acyl CoA Dehydrogenase Deficiency [SCAD Deficiency] Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency [SCHAD] Spectinomycin Action Pathway Stavudine Action Pathway Streptomycin Action Pathway Succinic semialdehyde dehydrogenase deficiency Telithromycin Action Pathway Tetracycline Action Pathway Thiamine Metabolism Thioguanine Action Pathway Tigecycline Action Pathway Tobramycin Action Pathway Transaldolase deficiency Transcription/Translation Trifunctional protein deficiency Troleandomycin Action Pathway Tyrosinemia Type 2 [or Richner-Hanhart syndrome] Tyrosinemia Type 3 [TYRO3] Urea Cycle Valproic Acid Metabolism Pathway Very-long-chain acyl coa dehydrogenase deficiency [VLCAD] Xanthine Dehydrogenase Deficiency [Xanthinuria] Xanthinuria type I Xanthinuria type II Zalcitabine Action Pathway Zidovudine Action Pathway
Author-emphasized biomarker in the paper(s)	Fahrmann et al. 2015

Lung cancer metabolomics studies that identify HMDB0000045 ("adenosine 5'-monophosphate", 'AMP', 'adenosine-5-phosphate')

Reference	Country	Specimen	Marker function	Participants (Case)						Participants (Control)
Reference	Country	Specimen	Marker function	Cancer type	Stage	Number	Gender (M,F)	Age mean (range) (M/F)	Smoking status	Type	Number	Gender (M,F)	Age mean (range) (M/F)	Smoking status
Fahrmann et al. 2015	–	serum	diagnosis	adenocarcinoma	I, II, III, IV	49	17, 32	65.9 ± 9.87	–	healthy	31	11, 20	64.1 ± 8.97	–
Fahrmann et al. 2015	–	serum	diagnosis	adenocarcinoma	I, II, III, IV	43	21, 22	67.3 ± 10.10	–	healthy	43	21, 22	65.9 ± 8.05	–
Mazzone et al. 2016	–	serum	–	adenocarcinoma, squamous cell carcinoma	I, II, III	94	55.3%, 44.7%	68.7	–	at-risk controls	190	50.5%, 49.5%	66.2	–
Moreno et al. 2018	–	tissue	therapy, diagnosis	adenocarcinoma	I, II, III	33	24, 9	62.11 ± 9.73	–	tumor vs. adjacent normal tissue	33	24, 9	62.11 ± 9.73	–
Yue et al. 2018	–	plasma	diagnosis	SCLC	–	20	–	–	–	healthy	20	–	–	–
Moreno et al. 2018	–	tissue	therapy, diagnosis	squamous cell carcinoma	I, II, III	35	35, 0	68.71 ± 7.46	–	tumor vs. adjacent normal tissue	35	35, 0	68.71 ± 7.46	–
Sun et al. 2019	–	serum	diagnosis	lung cancer	I, II, III, IV	31	21, 10	54.1 ± 9.9	smoker, non-smoker	healthy	29	15, 14	52.1 ± 14.6	smoker, non-smoker
Fahrmann et al. 2015	–	plasma	diagnosis	adenocarcinoma	I, II, III, IV	52	17, 35	65.9 ± 9.66	–	healthy	31	11, 20	64.1 ± 8.97	–
Fahrmann et al. 2015	–	plasma	diagnosis	adenocarcinoma	I, II, III, IV	43	21, 22	67.3 ± 10.10	–	healthy	43	21, 22	65.9 ± 8.05	–
Wikoff et al. 2015b	–	tissue	diagnosis	adenocarcinoma	I	39	15, 24	72.33 ± 8.78	smoker, non-smoker	tumor vs. adjacent normal tissue	39	15, 24	72.33 ± 8.78	smoker, non-smoker

Reference	Chromatography	Ion source	Positive/Negative mode	Mass analyzer	Identification level
Fahrmann et al. 2015	GC	EI	–	TOF	–
Fahrmann et al. 2015	GC	EI	–	TOF	–
Mazzone et al. 2016	LC	ESI	positive	linear ion-trap	MS/MS
Moreno et al. 2018	LC, GC	ESI, EI	positive, negative	LC: linear ion‐trap, GC: single‐quadrupole	LC: MS/MS
Yue et al. 2018	LC	ESI	positive, negative	QTRAP	MS/MS
Moreno et al. 2018	LC, GC	ESI, EI	positive, negative	LC: linear ion‐trap, GC: single‐quadrupole	LC: MS/MS
Sun et al. 2019	GC	–	–	–	–
Fahrmann et al. 2015	GC	EI	–	TOF	–
Fahrmann et al. 2015	GC	EI	–	TOF	–
Wikoff et al. 2015b	GC	EI	–	TOF	–

Reference	Data processing software	Database search
Fahrmann et al. 2015	–	UC Davis Metabolomics BinBase database
Fahrmann et al. 2015	–	UC Davis Metabolomics BinBase database
Mazzone et al. 2016	Metabolon LIMS system	Metabolon LIMS system
Moreno et al. 2018	–	KEGG, HMDB
Yue et al. 2018	Analyst, MultiQuant	–
Moreno et al. 2018	–	KEGG, HMDB
Sun et al. 2019	–	BinBase, KEGG
Fahrmann et al. 2015	–	UC Davis Metabolomics BinBase database
Fahrmann et al. 2015	–	UC Davis Metabolomics BinBase database
Wikoff et al. 2015b	BinBase	NIST11, BinBase

Differential analysis
Classification analysis

Reference	Difference method	Mean concentration (case)	Mean concentration (control)	Fold change (case/control)	P-value	FDR	VIP
Fahrmann et al. 2015	regress (by the covariates: age, gender and smoking history [packs per year]), permutation test	356 ± 1439	104 ± 156	3.41	0.707	0.861	–
Fahrmann et al. 2015	regress (by the covariates: age, gender and smoking history [packs per year]), permutation test	92 ± 68	112 ± 137	0.818	0.339	0.64	–
Mazzone et al. 2016	two- sample independent t test	1.5438223± 8.7152447	0.4087458± 0.4005822	3.77697409979503	0.0734333	0.142697019	–
Moreno et al. 2018	paired two‐sample t‐test, PLS-DA	–	–	2.04429921274098	0.000318731500175036	0.000920546898531848	–
Yue et al. 2018	OPLS-DA, student’s t-test	3240.20±1091.67 ng/mL	1211.94±319.08 ng/mL	0.0395548935615713	0.0000391	–	1.42
Moreno et al. 2018	paired two‐sample t‐test, PLS-DA	–	–	2.64653158861497	0.000000235876384571995	0.000000667715286300278	–
Sun et al. 2019	Student t test, PLS-DA	–	–	3.86407741984872	0.000000000022	0.00000000121	1.3045
Fahrmann et al. 2015	regress (by the covariates: age, gender and smoking history [packs per year]), permutation test	440 ± 346	203 ± 177	2.16	0	0.002	–
Fahrmann et al. 2015	regress (by the covariates: age, gender and smoking history [packs per year]), permutation test	259 ± 174	178 ± 422	1.46	0	0.004	–
Wikoff et al. 2015b	OPLS-DA	–	–	2.5	–	0.001	–

Reference	Classification method	Cutoff value	AUROC 95%CI	Sensitivity (%)	Specificity (%)	Accuracy (%)
Fahrmann et al. 2015	random forest	–	–	–	–	–
Fahrmann et al. 2015	random forest	–	–	–	–	–
Mazzone et al. 2016	–	–	–	–	–	–
Moreno et al. 2018	–	–	–	–	–	–
Yue et al. 2018	–	–	–	–	–	–
Moreno et al. 2018	–	–	–	–	–	–
Sun et al. 2019	ROC curve analysis	–	–	–	–	–
Fahrmann et al. 2015	random forest	–	maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan+adenosine-5-Phosphate=0.883 (0.812, 0.955)	–	–	68.7 maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan+adenosine-5-Phosphate=75.3
Fahrmann et al. 2015	random forest	–	maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan+adenosine-5-Phosphate=0.670 (0.552, 0.789)	67.4 maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan+adenosine-5-Phosphate=64.0	76.7 maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan+adenosine-5-Phosphate=90.7	72.1 maltose+maltotriose+cystine+3-Phosphoglycerate+citrulline+pyrophosphate+tryptophan+adenosine-5-Phosphate=77.3
Wikoff et al. 2015b	–	–	–	–	–	–