| Identification | Back Directory | [Name]
CYCLIC AMP | [CAS]
86594-35-6 | [Synonyms]
CAMP
3:5-CAMP
3',5'-CYCLIC AMP
CYCLIC AMP-3',5'
ADENOSINE CYCLOPHOSPHATE
ADENOSINE CYCLICPHOSPHATE
ADENOSINE 3'5'-MONOPHOSPHATE
ADENOSINE-3':5'-CYCLIC PHOSPHATE
ADENOSINE-3':5'-PHOSPHATE CYCLIC
ADENOSINE-3',5'-CYCLOPHOSPHORIC ACID
ADENOSINE-3',5'-CYCLIC PHOSPHATE H2O
ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE
ADENOSINE 3'-,5'-CYCLIC MONOPHOSPHATE
(-)-ADENOSINE 3',5'-CYCLIC MONOPHOSPHATE
ADENOSINE-3',5'-CYCLIC-MONOPHOSPHORIC ACID
ADENOSINE-3':5'-CYCLIC MONOPHOSPHORIC ACID
CAMP, ADENOSINE-3',5'-CYCLIC MONOPHOSPHATE
(S)-CYCLIC 3' 5'-(HYDROGEN PHOSPHATE) ADENOSINE
Adenosine, cyclic 3',5'-[hydrogen (S)-phosphate]
Sp-cAMP,Adenosine, cyclic3',5'-[hydrogen (S)-phosphate] (9CI) | [EINECS(EC#)]
200-492-9 | [Molecular Formula]
C10H12N5O6P | [MDL Number]
MFCD00005845 | [MOL File]
86594-35-6.mol | [Molecular Weight]
329.21 |
| Chemical Properties | Back Directory | [Melting point ]
260 °C (dec.)(lit.) | [storage temp. ]
2-8°C | [solubility ]
H2O: 10 mg/mL pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× | [form ]
powder | [color ]
white | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Uses]
Adenosine-3’,5’-cyclic Monophosphate is an Adenosine (A280400) derivative useful as anticancer agent. | [Enzyme inhibitor]
This prototypical second messenger (FWfree-acid = 329.21 g/mol; lmax = 259 nm; eM = 15400 M–1cm–1; Abbreviation: 3’,5’-cyclic AMP, 3’,5’-cAMP, opr cAMP), the isolation of which in the late 1950s earned Earl Sutherland his share of the 1971 Nobel Prize in Medicine & Physiology, activates susceptible protein kinases in signal transduction cascades. Elevated cAMP concentrations also activate cyclicAMP-gated ion channels; Exchange Proteins Activated by cAMP (or EPAC), such as RAPGEF3; and popeye domain-containing proteins (or Popdc). While many enzymes are weakly inhibited by cAMP (with inhibition constants typically in the 0.1 mM range or above), the peak physiologic concentration of cAMP rarely exceeds 1020 μM. Target(s): phosphate-activated glutaminase; glyceraldehyde3-phosphate dehydrogenase, Ki = 0.11 mM for the yeast enzyme; choline kinase; Bacillus subtilis ribonuclease; NAD(P)+ transhydrogenase, AB-specific; phosphofructokinase, weakly inhibited; hexokinase; adenosine deaminase; NAD+ nucleosidase, or NADase; poly(ADP-ribose) glycohydrolase; GMP synthetase; 5-phosphoribosylamine synthetase, or ribose-5phosphate:ammonia ligase; tyrosyl-tRNA synthetase, weakly inhibited; adenylylsulfatase; CDP-diacylglycerol diphosphatase; nucleotide diphosphatase, weakly inhibited; ATP diphosphatase, slight inhibition; keratan sulfotransferase, weakly inhibited; adenosylhomocysteinase; 6-phospho-b-glucosidase; prenyldiphosphatase; CMP-N-acylneuraminate phosphodiesterase; 2’,3’-cyclic-nucleotide 3’-phosphodiesterase, or cCMP phosphodiesterase; 3’,5’-cyclic-GMP phospho-diesterase, or cGMP phosphodiesterase; sphingomyelin phosphodiesterase; phosphoprotein phosphatase; 5’-nucleotidase; acid phosphatase; diacylglycerol cholinephosphotransferase; ethanolaminephosphotransferase; glucose-1-phosphate adenylyltransferase; nucleoside diphosphate kinase; AMP:thymidine kinase; diacylglycerol kinase; nucleoside phosphotransferase; 1phosphatidylinositol 4-kinase; NAD+ kinase (63; procollagen glucosyltransferase64; chitin synthase, weakly inhibited; glycogen phosphorylase, weakly inhibited; luciferase, firefly (Photinus-luciferin 4-monooxygenase, ATP-hydrolyzing. |
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