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CHEBI:16027 - adenosine 5'-monophosphate

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:
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 3.1.3.1 (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).
micronutrient  Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
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).
fundamental metabolite  Any metabolite produced by all living cells.
adenosine A1 receptor agonist  An agonist at the A1 receptor.
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
phosphate d'adénosineWHO MedNet
fosfato de adenosinaWHO MedNet
Synonyms  Source
AMPKEGG COMPOUND
Adenosine 5'-monophosphateKEGG COMPOUND
Adenylic acidKEGG COMPOUND
AdenylateKEGG COMPOUND
5'-AMPKEGG COMPOUND
5'-Adenylic acidKEGG COMPOUND
Manual XrefsDatabases
C00020KEGG COMPOUND
AMPPDBeChem
DB00131DrugBank
D02769KEGG DRUG
HMDB0000045HMDB
AMPMetaCyc
Adenylic_acidWikipedia
C00019347KNApSAcK
LSM-5914LINCS
92DrugCentral
Registry NumbersSources
Gmelin:38561Gmelin
Reaxys:54612Reaxys
CAS:61-19-8KEGG COMPOUND
CAS:61-19-8ChemIDplus
Citations