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CHEBI:16027 - adenosine 5'-monophosphate

Default Structure
ChEBI IDCHEBI:16027
ChEBI Nameadenosine 5'-monophosphate
Stars
DefinitionA purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.
Secondary ChEBI IDsCHEBI:2356, CHEBI:12056, CHEBI:13234, CHEBI:13235, CHEBI:13736, CHEBI:13740, CHEBI:22242, CHEBI:22245, CHEBI:40510, CHEBI:40726, CHEBI:40786, CHEBI:40826, CHEBI:47222
Last Modified18 April 2024
DownloadsMolfile
FormulaC10H14N5O7P
Net Charge0
Average Mass347.224
Monoisotopic Mass347.06308
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O
InChIInChI=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
InChIKeyUDMBCSSLTHHNCD-KQYNXXCUSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Biological Roles:
EC 3.1.3.1 (alkaline phosphatase) inhibitor  An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of alkaline phosphatase (EC 3.1.3.1).
fundamental metabolite  Any metabolite produced by all living cells.
micronutrient  Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
adenosine A1 receptor agonist  An agonist at the A1 receptor.
cofactor  An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor  An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of fructose-bisphosphatase (EC 3.1.3.11).
Application:
nutraceutical  A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
ChEBI Ontology
Outgoing Relation(s)
adenosine 5'-monophosphate (CHEBI:16027) has role adenosine A1 receptor agonist (CHEBI:65057)
adenosine 5'-monophosphate (CHEBI:16027) has role cofactor (CHEBI:23357)
adenosine 5'-monophosphate (CHEBI:16027) has role EC 3.1.3.1 (alkaline phosphatase) inhibitor (CHEBI:63332)
adenosine 5'-monophosphate (CHEBI:16027) has role EC 3.1.3.11 (fructose-bisphosphatase) inhibitor (CHEBI:65056)
adenosine 5'-monophosphate (CHEBI:16027) has role fundamental metabolite (CHEBI:78675)
adenosine 5'-monophosphate (CHEBI:16027) has role micronutrient (CHEBI:27027)
adenosine 5'-monophosphate (CHEBI:16027) has role nutraceutical (CHEBI:50733)
adenosine 5'-monophosphate (CHEBI:16027) is a adenosine 5'-phosphate (CHEBI:37096)
adenosine 5'-monophosphate (CHEBI:16027) is a purine ribonucleoside 5'-monophosphate (CHEBI:37021)
adenosine 5'-monophosphate (CHEBI:16027) is conjugate acid of adenosine 5'-monophosphate(2−) (CHEBI:456215)
adenosine 5'-monophosphate (CHEBI:16027) is conjugate base of adenosine 5'-monophosphate(1+) (CHEBI:40721)
Incoming Relation(s)
(S)-lactoyl-AMP(1−) (CHEBI:231470) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
(3-aminopropyl)(L-aspartyl-1-amino)phosphoryl-5'-adenosine (CHEBI:60869) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N-(5'-adenylyl)morpholine (CHEBI:131578) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N-{N-[9-(5-O-phosphono-β-D-ribofuranosyl)purin-6-yl]-N-methylcarbamoyl}threonine (CHEBI:40643) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N-{N-[9-(5-O-phosphono-β-D-ribofuranosyl)purin-6-yl]carbamoyl}threonine (CHEBI:45796) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N1-methyladenosine 5'-monophosphate (CHEBI:74736) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N6-(1,2-dicarboxyethyl)-AMP (CHEBI:15919) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N6-(5'-adenylyl)-L-lysine (CHEBI:21868) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N6-L-threonylcarbamoyladenine 5'-monophosphate (CHEBI:74637) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N6-dimethylallyladenosine 5'-monophosphate (CHEBI:21865) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N6-methyl-AMP (CHEBI:40196) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
N6,N6-dimethyl-AMP (CHEBI:43986) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
O-(5'-adenylyl)-L-threonine (CHEBI:21928) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
O4'-(5'-adenylyl)-L-tyrosine (CHEBI:21988) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
trans-4-coumaroyl-AMP(1−) (CHEBI:192348) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
trans-caffeoyl-AMP(1−) (CHEBI:192349) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
trans-feruloyl-AMP(1−) (CHEBI:192350) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
trans-sinapoyl-AMP(1−) (CHEBI:192469) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
D-alanyl-AMP (CHEBI:139296) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-alanyl-AMP zwitterion (CHEBI:144940) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-arginyl-AMP (CHEBI:229719) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-glutamyl-AMP(1−) (CHEBI:144941) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-homocysteinyl-AMP zwitterion (CHEBI:233461) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-isoleucyl-AMP zwitterion (CHEBI:178002) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-lysyl-5'-AMP(1+) (CHEBI:176581) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-seryl-AMP (CHEBI:61645) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-seryl-AMP(1−) (CHEBI:61231) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-threonyl-AMP (CHEBI:64851) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-threonyl-AMP(1−) (CHEBI:64847) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-threonylcarbamoyladenylate (CHEBI:73687) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-tryptophyl-AMP(1−) (CHEBI:144939) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
1-(5-O-phosphono-β-D-ribofuranosyl)-5-(sulfanylcarbonyl)pyridinium-3-carbonyl adenylate (CHEBI:137397) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
17-(4-hydroxyphenyl)heptadecanoyl-AMP (CHEBI:127781) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
19-(4-hydroxyphenyl)nonadecanoyl-AMP (CHEBI:128120) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-amino-3-hydroxy-4-methylbenzoyl-AMP (CHEBI:112505) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-hydroxy-AMP (CHEBI:65129) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-hydroxybenzoyl-AMP (CHEBI:86457) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-methyladenosine 5'-monophosphate (CHEBI:74770) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-methylthio-N6-L-threonylcarbamoyladenine 5'-monophosphate (CHEBI:74651) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-methylthio-N6-dimethylallyladenine 5'-monophosphate (CHEBI:74646) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-oxo-AMP (CHEBI:71396) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-thio-N6-L-threonylcarbamoyladenine 5'-monophosphate (CHEBI:74649) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2-thio-N6-dimethylallyladenine 5'-monophosphate (CHEBI:74643) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2,3-dihydroxybenzoyl 5'-adenylate (CHEBI:15572) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2'-O-methyladenosine 5'-monophosphate (CHEBI:40460) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3,4-dihydroxybenzoyl-AMP(1−) (CHEBI:144942) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-(N-formyl-L-methionyl)-AMP (CHEBI:131556) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-alanyl-AMP (CHEBI:131551) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-arginyl-AMP (CHEBI:131552) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-asparaginyl-AMP (CHEBI:131553) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-aspartyl-AMP (CHEBI:131554) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-cysteinyl-AMP (CHEBI:131555) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-glutaminyl-AMP (CHEBI:131558) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-glutamyl-AMP (CHEBI:131559) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-histidyl-AMP (CHEBI:131566) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-isoleucyl-AMP (CHEBI:131567) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-leucyl-AMP (CHEBI:131568) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-lysyl-AMP (CHEBI:131569) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-methionyl-AMP (CHEBI:131570) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-phenylalanyl-AMP (CHEBI:131571) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-prolyl-AMP (CHEBI:131572) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-seryl-AMP (CHEBI:131573) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-threonyl-AMP (CHEBI:131574) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-tryptophyl-AMP (CHEBI:131575) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-tyrosyl-AMP (CHEBI:131576) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-L-valyl-AMP (CHEBI:131577) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-dehydro-AMP (CHEBI:28722) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
3'-glycyl-AMP (CHEBI:131560) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
4-hydroxybenzoyl-AMP (CHEBI:86433) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
4'-adenylkanamycin A (CHEBI:137400) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
5-carboxy-1-(5-O-phosphono-β-D-ribofuranosyl)pyridinium-3-carbonyl adenylate (CHEBI:137396) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
8-methyladenosine 5'-monophosphate (CHEBI:74788) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
9-ribosyl-trans-zeatin 5'-monophosphate (CHEBI:71719) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
adenosine 5'-monophosphate 1-oxide (CHEBI:35483) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
adenosine 5'-phosphoramidate (CHEBI:16771) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
adenosine-5'-phosphate-2',3'-cyclic phosphate (CHEBI:40403) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
agrocin 84 (CHEBI:82809) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
AMP-sugar (CHEBI:20853) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
benzoyl-AMP (CHEBI:156046) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
biotinyl-5'-AMP (CHEBI:3110) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
carbamoyl adenylate (CHEBI:73680) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
coenzyme F390-A (CHEBI:62784) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
fatty acyl-AMP (CHEBI:83621) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
glycyl-AMP (CHEBI:64849) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
glycyl-AMP(1−) (CHEBI:64846) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
lipoyl-AMP (CHEBI:55451) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
microcin c (CHEBI:82754) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
propanoyl-AMP (CHEBI:62415) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
propanoyl-AMP(1−) (CHEBI:62371) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
β-alanyl-5'-AMP zwitterion (CHEBI:192795) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
adenosine 5'-monophosphate(1+) (CHEBI:40721) is conjugate acid of adenosine 5'-monophosphate (CHEBI:16027)
adenosine 5'-monophosphate(2−) (CHEBI:456215) is conjugate base of adenosine 5'-monophosphate (CHEBI:16027)
adenosine 5'-monophosphate residue (CHEBI:50306) is substituent group from adenosine 5'-monophosphate (CHEBI:16027)
AMP 3'-end residue (CHEBI:53112) is substituent group from adenosine 5'-monophosphate (CHEBI:16027)
AMP 5'-end residue (CHEBI:53098) is substituent group from adenosine 5'-monophosphate (CHEBI:16027)
IUPAC Name 
5'-adenylic acid
INNs  Source
adenosine phosphateWHO MedNet
adenosini phosphasWHO MedNet
fosfato de adenosinaWHO MedNet
phosphate d'adénosineWHO MedNet
Synonyms  Source
5'-Adenosine monophosphateKEGG COMPOUND
5'-Adenylic acidKEGG COMPOUND
5'-AMPKEGG COMPOUND
5'-O-phosphonoadenosineIUBMB
adenosine 5'-(dihydrogen phosphate)IUBMB
adenosine-5'PIUBMB
Manual XrefsDatabases
92DrugCentral
Adenylic_acidWikipedia
AMPPDBeChem
AMPMetaCyc
C00019347KNApSAcK
C00020KEGG COMPOUND
D02769KEGG DRUG
DB00131DrugBank
HMDB0000045HMDB
LSM-5914LINCS
Registry NumbersSources
Gmelin:38561Gmelin
Reaxys:54612Reaxys
CAS:61-19-8KEGG COMPOUND
CAS:61-19-8ChemIDplus
Citations