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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N5O6P
Molecular Weight 329.2059
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADENOSINE CYCLIC PHOSPHATE

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O

InChI

InChIKey=IVOMOUWHDPKRLL-KQYNXXCUSA-N
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

HIDE SMILES / InChI

Molecular Formula C10H12N5O6P
Molecular Weight 329.2059
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17018604

Cyclic adenosine monophosphate (cAMP, cyclic AMP or 3'-5'-cyclic adenosine monophosphate) is a molecule that is important in many biological processes; it is derived from adenosine triphosphate (ATP) by adenylate cyclase located on the inner side of the plasma membrane and anchored at various locations in the interior of the cell. Around 1960 Earl W. Sutherland, Jr. showed that cyclic adenosine monophosphate (cAMP) serves as the secondary messenger within the cell. Cyclic AMP works by activating protein kinase A (PKA, or cAMP-dependent protein kinase). PKA is normally inactive as a tetrameric holoenzyme, consisting of two catalytic and two regulatory units with the regulatory units blocking the catalytic centers of the catalytic units. Cyclic AMP binds to specific locations on the regulatory units of the protein kinase, and causes dissociation between the regulatory and catalytic subunits, thus enabling those catalytic units to phosphorylate substrate proteins. It was discovered, that melanocytes require the RAS/RAF/MEK/ERK and the cyclic AMP (cAMP) signaling pathways to maintain the fine balance between proliferation and differentiation. cAMP suppressed CRAF activity in melanocytes and that was essential to suppress the oncogenic potential of CRAF in the cells. When RAS was mutated in melanoma, the cells switched their signaling from BRAF to CRAF. That switch was accompanied by dysregulated cAMP signaling, a step that was necessary to allow CRAF to signal to MEK. Thus, a fundamental switch in RAF isoform usage occurs when RAS was mutated in melanoma, and that occurs in the context of disrupted cAMP signaling. These data have important implications for the development of therapeutic strategies to treat this life-threatening disease.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P13861
Gene ID: 5576.0
Gene Symbol: PRKAR2A
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
pH sensing via bicarbonate-regulated "soluble" adenylyl cyclase (sAC).
2013 Nov 25
The glucagon-like peptide-1 analogue exendin-4 reverses impaired intracellular Ca(2+) signalling in steatotic hepatocytes.
2016 Sep

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:39 GMT 2023
Record UNII
E0399OZS9N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADENOSINE CYCLIC PHOSPHATE
INCI  
INCI  
Official Name English
3',5'-AMP
Common Name English
ADENOSINE-3':5'-CYCLIC MONOPHOSPHORIC ACID (3:5-CYCLIC AMP)
Common Name English
CYCLIC ADENOSINE 3',5'-PHOSPHATE
Common Name English
CYCLIC AMP [MI]
Common Name English
ADENOSINUM CYCLOPHOSPHORICUM [HPUS]
Common Name English
AMPC
Code English
ADENOSINUM CYCLOPHOSPHORICUM
HPUS  
Common Name English
NSC-94017
Code English
ADENOSINE CYCLIC-3',5'-(HYDROPHOSPHATE)
Common Name English
ADENOSINE 3',5'-PHOSPHATE
Common Name English
ADENOSINE 3',5'-CYCLOPHOSPHATE
Common Name English
CYCLIC-AMP
Common Name English
NSC-143670
Code English
3',5'-CYCLIC AMP
Common Name English
CYCLIC ADENOSINE MONOPHOSPHATE
Common Name English
ADENOSINE 3',5'-CYCLIC MONOPHOSPHATE
Common Name English
ADENOSINE, CYCLIC 3',5'-(HYDROGEN PHOSPHATE)
Common Name English
CAMP
Common Name English
CYCLIC 3',5'-ADENYLIC ACID
Common Name English
CYCLIC 3',5'-AMP
Common Name English
Cyclic amp [WHO-DD]
Common Name English
CYCLIC AMP
MI   WHO-DD  
Common Name English
ADENOSINE CYCLIC PHOSPHATE [INCI]
Common Name English
ADENOSINE CYCLIC 3',5'-PHOSPHATE
Common Name English
ADENOSINE 3',5'-MONOPHOSPHATE
Common Name English
ADENOSINE CYCLIC 3',5'-MONOPHOSPHATE
Common Name English
Classification Tree Code System Code
LOINC 14584-7
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
NCI_THESAURUS C1903
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
Code System Code Type Description
WIKIPEDIA
CYCLIC ADENOSINE MONOPHOSPHATE
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
DAILYMED
E0399OZS9N
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
NSC
94017
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
PUBCHEM
6076
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PRIMARY
MERCK INDEX
m3971
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-492-9
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PRIMARY
CHEBI
84597
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PRIMARY
CHEBI
58165
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
RXCUI
1314330
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PRIMARY RxNorm
NSC
143670
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PRIMARY
FDA UNII
E0399OZS9N
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
EVMPD
SUB124506
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
NCI_THESAURUS
C208
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
DRUG BANK
DB02527
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
MESH
D000242
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
CAS
60-92-4
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
CHEBI
17489
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
SMS_ID
100000145750
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID8040436
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
CHEBI
2676
Created by admin on Fri Dec 15 15:03:39 GMT 2023 , Edited by admin on Fri Dec 15 15:03:39 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> SUBSTRATE
Km
PARENT -> CONSTITUENT ALWAYS PRESENT
LABELED -> NON-LABELED
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY