CHEBI:17489 - 3',5'-cyclic AMP

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ChEBI Name 3',5'-cyclic AMP
ChEBI ID CHEBI:17489
Definition A 3',5'-cyclic purine nucleotide having having adenine as the nucleobase.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1325, CHEBI:41588, CHEBI:11673, CHEBI:19827
Supplier Information ChemicalBook:CB7852954, eMolecules:478134, ZINC000000895323
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Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes. Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma–active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form.
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Formula C10H12N5O6P
Net Charge 0
Average Mass 329.20614
Monoisotopic Mass 329.05252
InChI InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChIKey IVOMOUWHDPKRLL-KQYNXXCUSA-N
SMILES Nc1ncnc2n(cnc12)[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3',5'-cyclic AMP (CHEBI:17489) has role Escherichia coli metabolite (CHEBI:76971)
3',5'-cyclic AMP (CHEBI:17489) has role human metabolite (CHEBI:77746)
3',5'-cyclic AMP (CHEBI:17489) has role mouse metabolite (CHEBI:75771)
3',5'-cyclic AMP (CHEBI:17489) is a 3',5'-cyclic purine nucleotide (CHEBI:19834)
3',5'-cyclic AMP (CHEBI:17489) is a adenyl ribonucleotide (CHEBI:61296)
3',5'-cyclic AMP (CHEBI:17489) is conjugate acid of 3',5'-cyclic AMP(1−) (CHEBI:58165)
Incoming (Rp)-cAMPS (CHEBI:84622) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
(Sp)-8-bromo-cAMPS (CHEBI:84619) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
(Sp)-cAMPS (CHEBI:84615) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
1-NO-cAMP (CHEBI:84597) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
2-(6-aminohexylamino)-cAMP (CHEBI:84604) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
2-(dimethylamino)-cAMP (CHEBI:84598) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
8-(4-chlorophenylthio)-cAMP (CHEBI:84612) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
8-(6-aminohexylamino)-cAMP (CHEBI:84613) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
8-(6-aminohexylthio)-cAMP (CHEBI:84614) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
8-Br-cAMP (CHEBI:64211) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
8-PIP-cAMP (CHEBI:145730) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
N6-(6-aminohexyl)-cAMP (CHEBI:84606) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
N6-butyryl-cAMP (CHEBI:84605) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
bucladesine (CHEBI:50095) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
6-(dimethylamino)-cPuMP (CHEBI:84627) has parent hydride 3',5'-cyclic AMP (CHEBI:17489)
3',5'-cyclic AMP(1−) (CHEBI:58165) is conjugate base of 3',5'-cyclic AMP (CHEBI:17489)
IUPAC Name
adenosine 3',5'-(hydrogen phosphate)
Synonyms Sources
3',5'-Cyclic AMP KEGG COMPOUND
adenosine 3',5'-cyclic monophosphate NIST Chemistry WebBook
Adenosine 3',5'-cyclic phosphate KEGG COMPOUND
Adenosine 3',5'-phosphate KEGG COMPOUND
ADENOSINE-3',5'-CYCLIC-MONOPHOSPHATE PDBeChem
cAMP KEGG COMPOUND
Cyclic adenylic acid KEGG COMPOUND
Cyclic AMP KEGG COMPOUND
Manual Xrefs Databases
C00001497 KNApSAcK
C00575 KEGG COMPOUND
CAMP MetaCyc
CMP PDBeChem
Cyclic_AMP Wikipedia
DB02527 DrugBank
HMDB0000058 HMDB
View more database links
Registry Numbers Types Sources
52645 Reaxys Registry Number Reaxys
60-92-4 CAS Registry Number NIST Chemistry WebBook
60-92-4 CAS Registry Number ChemIDplus
Citations Types Sources
16295522 PubMed citation Europe PMC
18372334 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
Last Modified
02 January 2020