adenosine 5'-monophosphate (CHEBI:16027) (2024)

CHEBI:16027 - adenosine 5'-monophosphate

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adenosine 5'-monophosphate (CHEBI:16027) (1) adenosine 5'-monophosphate (CHEBI:16027) (2)
ChEBI Name adenosine 5'-monophosphate
ChEBI ID CHEBI:16027
Definition A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.
Stars adenosine 5'-monophosphate (CHEBI:16027) (3)adenosine 5'-monophosphate (CHEBI:16027) (4)adenosine 5'-monophosphate (CHEBI:16027) (5) This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:13740, CHEBI:40510, CHEBI:22242, CHEBI:40726, CHEBI:40786, CHEBI:40826, CHEBI:47222, CHEBI:12056, CHEBI:2356, CHEBI:13736, CHEBI:13234, CHEBI:13235, CHEBI:22245
Supplier Information
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adenosine 5'-monophosphate (CHEBI:16027) (6)
Read full article at Wikipedia
Formula C10H14N5O7P
Net Charge 0
Average Mass 347.22120
Monoisotopic Mass 347.06308
InChI InChI=1S/C10H14N5O7P/c11-adenosine 5'-monophosphate (CHEBI:16027) (7)8-adenosine 5'-monophosphate (CHEBI:16027) (8)5-adenosine 5'-monophosphate (CHEBI:16027) (9)9(13-adenosine 5'-monophosphate (CHEBI:16027) (10)2-adenosine 5'-monophosphate (CHEBI:16027) (11)12-adenosine 5'-monophosphate (CHEBI:16027) (12)8)adenosine 5'-monophosphate (CHEBI:16027) (13)15(3-adenosine 5'-monophosphate (CHEBI:16027) (14)14-adenosine 5'-monophosphate (CHEBI:16027) (15)5)adenosine 5'-monophosphate (CHEBI:16027) (16)10-adenosine 5'-monophosphate (CHEBI:16027) (17)7(17)adenosine 5'-monophosphate (CHEBI:16027) (18)6(16)adenosine 5'-monophosphate (CHEBI:16027) (19)4(22-adenosine 5'-monophosphate (CHEBI:16027) (20)10)adenosine 5'-monophosphate (CHEBI:16027) (21)1-adenosine 5'-monophosphate (CHEBI:16027) (22)21-adenosine 5'-monophosphate (CHEBI:16027) (23)23(18,19)adenosine 5'-monophosphate (CHEBI:16027) (24)20/h2-adenosine 5'-monophosphate (CHEBI:16027) (25)4,6-adenosine 5'-monophosphate (CHEBI:16027) (26)7,10,16-adenosine 5'-monophosphate (CHEBI:16027) (27)17H,1H2,(H2,11,12,13)adenosine 5'-monophosphate (CHEBI:16027) (28)(H2,18,19,20)adenosine 5'-monophosphate (CHEBI:16027) (29)/t4-adenosine 5'-monophosphate (CHEBI:16027) (30),6-adenosine 5'-monophosphate (CHEBI:16027) (31),7-adenosine 5'-monophosphate (CHEBI:16027) (32),10-adenosine 5'-monophosphate (CHEBI:16027) (33)/m1/s1
InChIKey UDMBCSSLTHHNCD-KQYNXXCUSA-N
SMILES Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): micronutrient

Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.

fundamental metabolite

Any metabolite produced by all living cells.

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).

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).

adenosine A1 receptor agonist

An agonist at the A

1

receptor.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-alanyl-5'-AMP zwitterion (CHEBI:192795) 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)
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'-O-methyladenosine 5'-monophosphate (CHEBI:40460) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
2,3-dihydroxybenzoyl 5'-adenylate (CHEBI:15572) 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)
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)
3,4-dihydroxybenzoyl-AMP(1−) (CHEBI:144942) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
4'-adenylkanamycin A (CHEBI:137400) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
4-hydroxybenzoyl-AMP (CHEBI:86433) 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)
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,N6-dimethyl-AMP (CHEBI:43986) 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)
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(1+) (CHEBI:144944) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
L-glutamyl-AMP(1−) (CHEBI:144941) 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)
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)
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 Sources
adenosine phosphate WHO MedNet
adenosini phosphas adenosine 5'-monophosphate (CHEBI:16027) (34) WHO MedNet
fosfato de adenosina adenosine 5'-monophosphate (CHEBI:16027) (35) WHO MedNet
phosphate d'adénosine adenosine 5'-monophosphate (CHEBI:16027) (36) WHO MedNet
Synonyms Sources
5'-Adenosine monophosphate KEGG COMPOUND
5'-Adenylic acid KEGG COMPOUND
5'-AMP KEGG COMPOUND
5'-O-phosphonoadenosine CBN
adenosine 5'-(dihydrogen phosphate) CBN
Adenosine 5'-monophosphate KEGG COMPOUND
Adenosine 5'-phosphate KEGG COMPOUND
ADENOSINE MONOPHOSPHATE PDBeChem
adenosine phosphate ChemIDplus
Adenosine-5'-monophosphoric acid HMDB
adenosine-5'P CBN
Adenylate KEGG COMPOUND
Adenylic acid KEGG COMPOUND
Ado5'P CBN
AMP KEGG COMPOUND
pA ChEBI
PAdo CBN
Manual Xrefs Databases
92 DrugCentral
Adenylic_acid Wikipedia
AMP PDBeChem
AMP MetaCyc
C00019347 KNApSAcK
C00020 KEGG COMPOUND
D02769 KEGG DRUG
DB00131 DrugBank
HMDB0000045 HMDB
LSM-5914 LINCS
MOL000174 COMe
View more database links
Registry Numbers Types Sources
38561 Gmelin Registry Number Gmelin
54612 Reaxys Registry Number Reaxys
54612 Beilstein Registry Number Beilstein
61-19-8 CAS Registry Number KEGG COMPOUND
61-19-8 CAS Registry Number ChemIDplus
Citations adenosine 5'-monophosphate (CHEBI:16027) (37) Types Sources
11307758 PubMed citation Europe PMC
12020809 PubMed citation Europe PMC
12181610 PubMed citation Europe PMC
15148540 PubMed citation Europe PMC
15946677 PubMed citation Europe PMC
16091942 PubMed citation Europe PMC
16250233 PubMed citation Europe PMC
16295522 PubMed citation Europe PMC
17439666 PubMed citation Europe PMC
22215671 PubMed citation Europe PMC
22624049 PubMed citation Europe PMC
2559771 PubMed citation Europe PMC
Last Modified
01 July 2020
adenosine 5'-monophosphate (CHEBI:16027) (2024)
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