CHEBI:145730 - 8-PIP-cAMP

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ChEBI Name 8-PIP-cAMP
ChEBI ID CHEBI:145730
Definition A cyclic adenyl ribonucleotide that is cAMP (cyclic adenosine 3',5'-phosphate) in which the hydrogen at position 8 has been replaced by a piperidin-1-yl group. A selective cAMP-dependent protein kinase A (PKA) activator and cAMP analogue with high selectivity for site A of PKA type I and for site B of PKA type II.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kalpana P
Supplier Information
Download Molfile XML SDF
Formula C15H21N6O6P
Net Charge 0
Average Mass 412.343
Monoisotopic Mass 412.12602
InChI InChI=1S/C15H21N6O6P/c16-12-9-13(18-7-17-12)21(15(19-9)20-4-2-1-3-5-20)14-10(22)11-8(26-14)6-25-28(23,24)27-11/h7-8,10-11,14,22H,1-6H2,(H,23,24)(H2,16,17,18)/t8-,10-,11-,14-/m1/s1
InChIKey KBRGEUZQYNIAKB-IDTAVKCVSA-N
SMILES N1=CN=C2C(N=C(N2[C@@H]3O[C@@H]4COP(O[C@H]4[C@H]3O)(=O)O)N5CCCCC5)=C1N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): protein kinase A agonist
A protein kinase agonist that selectively binds to and activates a protein kinase A receptor
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 8-PIP-cAMP (CHEBI:145730) has functional parent 3',5'-cyclic AMP (CHEBI:17489)
8-PIP-cAMP (CHEBI:145730) has role antineoplastic agent (CHEBI:35610)
8-PIP-cAMP (CHEBI:145730) has role protein kinase A agonist (CHEBI:78547)
8-PIP-cAMP (CHEBI:145730) is a 3',5'-cyclic purine nucleotide (CHEBI:19834)
8-PIP-cAMP (CHEBI:145730) is a adenyl ribonucleotide (CHEBI:61296)
8-PIP-cAMP (CHEBI:145730) is a piperidines (CHEBI:26151)
8-PIP-cAMP (CHEBI:145730) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
8-piperidin-1-yladenosine 3',5'-(hydrogen phosphate)
Synonyms Sources
(4aR,6R,7R,7aS)-6-[6-amino-8-(piperidin-1-yl)-9H-purin-9-yl]tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide IUPAC
8-piperidinoadenosine-3',5'-cyclic monophosphate ChEBI
Citations Waiting for Citations Types Sources
21695205 PubMed citation Europe PMC
25863490 PubMed citation Europe PMC
26405036 PubMed citation Europe PMC
9774149 PubMed citation Europe PMC
Last Modified
02 January 2020