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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (158)transporters (7) Show 165 proteins XML

enzymes (158)transporters (7) Show 165 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-11-15 21:04:27 UTC

HMDB ID

HMDB0000058

Secondary Accession Numbers

HMDB00058

Metabolite Identification

Common Name

Cyclic AMP

Description

Cyclic AMP (cAMP) or cyclic adenosine monophosphate is an adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. cAMP is found in all organisms ranging from bacteria to plants to animals. In humans and other mammals it is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon and ACTH. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the inner side of cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase. cAMP is primarily used for intracellular signal transduction, such as transferring into cells the effects of hormones like glucagon and adrenaline, which cannot pass through the plasma membrane. cAMP is also involved in the activation of protein kinases. In addition, cAMP binds to and regulates the function of ion channels such as the HCN channels. Hyperpolarization-activated cyclic nucleotide-gated (HCN) channels are integral membrane proteins that serve as nonselective voltage-gated cation channels in the plasma membranes of heart and brain cells. HCN channels are sometimes referred to as pacemaker channels because they help to generate rhythmic activity within groups of heart and brain cells.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000058
     RDKit          3D
Cyclic AMP
 34 37  0  0  0  0  0  0  0  0999 V2000
   -5.5227   -0.6321   -0.3239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383    0.3834   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955    1.6749   -0.0521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8168    2.5829    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5196    2.2089   -0.1413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796    0.9279   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.0044   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037   -1.1931   -0.6137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2797   -1.0026   -0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9970    0.3020   -0.5194 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300    0.8986   -0.5315 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1164    0.2048   -1.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1170   -0.4331   -0.7427 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5350   -1.7481   -1.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.2229   -0.6589 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354   -1.2660    0.6107 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9025   -2.1625    1.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2039   -0.0987    0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.5810    1.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.5439    0.6966 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9526    0.7730    0.8430 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8997    1.7497    1.0902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0411   -0.9024   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7528   -1.1545    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0840    3.6244    0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -1.8034   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2778    1.9886   -0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253    0.2270   -0.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.5166   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -1.5648   -2.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402    0.5759    0.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.4201    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856    0.7287    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145    2.3907    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  7  2  1  0
 21 11  1  0
 10  6  1  0
 20 13  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  6
 13 28  1  1
 14 29  1  0
 14 30  1  0
 18 31  1  0
 20 32  1  6
 21 33  1  1
 22 34  1  0
M  END


  Mrv1652303182019232D          

 24 27  0  0  0  0            999 V2000
 9996.4847 9997.8129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9794 9997.5914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2121 9999.9527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6598 9999.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1077 9998.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3627 9997.9378    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1696 9997.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1385 9999.6509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4711 9999.1659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.7260 9998.3813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.5510 9998.3813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0359 9997.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.670510000.2055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.845510000.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5905 9999.4208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.3512 9999.5718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.6808 9999.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3459 9998.1123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.0995 9997.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.7670 9998.2617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.2580 9998.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9253 9999.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8059 9999.1659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.3346 9997.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  1  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  6  0  0  0
  4  9  1  0  0  0  0
  9  3  1  6  0  0  0
  7 10  1  0  0  0  0
 10  2  1  1  0  0  0
 17 20  2  0  0  0  0
 19 20  1  0  0  0  0
 18 19  2  0  0  0  0
 17 16  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 21 18  1  0  0  0  0
 13 14  2  0  0  0  0
 13 22  1  0  0  0  0
 14 15  1  0  0  0  0
 15 21  1  0  0  0  0
 23 15  1  1  0  0  0
 11 23  1  0  0  0  0
  8 23  1  0  0  0  0
  6 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000058

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
IVOMOUWHDPKRLL-KQYNXXCUSA-N

> <FORMULA>
C10H12N5O6P

> <MOLECULAR_WEIGHT>
329.2059

> <EXACT_MASS>
329.052519653

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.42295790219419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one

> <ALOGPS_LOGP>
-2.29

> <JCHEM_LOGP>
-3.3924794780069596

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.588619397066793

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8292367774944256

> <JCHEM_PKA_STRONGEST_BASIC>
3.9248049140967343

> <JCHEM_POLAR_SURFACE_AREA>
154.84

> <JCHEM_REFRACTIVITY>
70.2895

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000058
     RDKit          3D
Cyclic AMP
 34 37  0  0  0  0  0  0  0  0999 V2000
   -5.5227   -0.6321   -0.3239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383    0.3834   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955    1.6749   -0.0521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8168    2.5829    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5196    2.2089   -0.1413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796    0.9279   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.0044   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037   -1.1931   -0.6137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2797   -1.0026   -0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9970    0.3020   -0.5194 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300    0.8986   -0.5315 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1164    0.2048   -1.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1170   -0.4331   -0.7427 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5350   -1.7481   -1.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.2229   -0.6589 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354   -1.2660    0.6107 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9025   -2.1625    1.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2039   -0.0987    0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.5810    1.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.5439    0.6966 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9526    0.7730    0.8430 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8997    1.7497    1.0902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0411   -0.9024   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7528   -1.1545    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0840    3.6244    0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -1.8034   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2778    1.9886   -0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253    0.2270   -0.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.5166   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -1.5648   -2.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402    0.5759    0.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.4201    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856    0.7287    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145    2.3907    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  7  2  1  0
 21 11  1  0
 10  6  1  0
 20 13  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  6
 13 28  1  1
 14 29  1  0
 14 30  1  0
 18 31  1  0
 20 32  1  6
 21 33  1  1
 22 34  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  O   UNK     0    8660.1058662.584   0.000  0.00  0.00           O+0
HETATM    2  H   UNK     0    8664.7628662.171   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0    8663.3298666.578   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0    8662.2988665.426   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8661.2688664.282   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0    8661.7448662.817   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0    8663.2508662.497   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8665.0598666.015   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8663.8138665.110   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.2898663.645   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.8298663.645   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8666.7348662.399   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0    8669.7858667.050   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    8668.2458667.050   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    8667.7698665.585   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0    8672.9228665.867   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    8671.6718664.953   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0    8669.1798663.143   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0    8670.5868662.517   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8671.8328663.422   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    8669.0158664.680   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.2618665.585   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8666.3048665.110   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8661.6918661.278   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   10                                                            
CONECT    3    9                                                            
CONECT    4    5    9                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    1   24                                             
CONECT    7    6   10                                                       
CONECT    8    9   23                                                       
CONECT    9   10    8    4    3                                             
CONECT   10    9   11    7    2                                             
CONECT   11   10   12   23                                                  
CONECT   12   11                                                            
CONECT   13   14   22                                                       
CONECT   14   13   15                                                       
CONECT   15   14   21   23                                                  
CONECT   16   17                                                            
CONECT   17   20   16   22                                                  
CONECT   18   19   21                                                       
CONECT   19   20   18                                                       
CONECT   20   17   19                                                       
CONECT   21   22   18   15                                                  
CONECT   22   21   17   13                                                  
CONECT   23   15   11    8                                                  
CONECT   24    6                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000058
HETATM    1  N1  UNL     1      -5.523  -0.632  -0.324  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.538   0.383  -0.252  1.00  0.00           C  
HETATM    3  N2  UNL     1      -4.795   1.675  -0.052  1.00  0.00           N  
HETATM    4  C2  UNL     1      -3.817   2.583   0.005  1.00  0.00           C  
HETATM    5  N3  UNL     1      -2.520   2.209  -0.141  1.00  0.00           N  
HETATM    6  C3  UNL     1      -2.180   0.928  -0.346  1.00  0.00           C  
HETATM    7  C4  UNL     1      -3.213   0.004  -0.401  1.00  0.00           C  
HETATM    8  N4  UNL     1      -2.604  -1.193  -0.614  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.280  -1.003  -0.682  1.00  0.00           C  
HETATM   10  N5  UNL     1      -0.997   0.302  -0.519  1.00  0.00           N  
HETATM   11  C6  UNL     1       0.330   0.899  -0.531  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.116   0.205  -1.417  1.00  0.00           O  
HETATM   13  C7  UNL     1       2.117  -0.433  -0.743  1.00  0.00           C  
HETATM   14  C8  UNL     1       2.535  -1.748  -1.334  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.632  -2.223  -0.659  1.00  0.00           O  
HETATM   16  P1  UNL     1       4.135  -1.266   0.611  1.00  0.00           P  
HETATM   17  O3  UNL     1       4.903  -2.163   1.586  1.00  0.00           O  
HETATM   18  O4  UNL     1       5.204  -0.099   0.027  1.00  0.00           O  
HETATM   19  O5  UNL     1       2.851  -0.581   1.470  1.00  0.00           O  
HETATM   20  C9  UNL     1       1.692  -0.544   0.697  1.00  0.00           C  
HETATM   21  C10 UNL     1       0.953   0.773   0.843  1.00  0.00           C  
HETATM   22  O6  UNL     1       1.900   1.750   1.090  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.041  -0.902  -1.187  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.753  -1.154   0.549  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.084   3.624   0.171  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.572  -1.803  -0.846  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.278   1.989  -0.768  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.025   0.227  -0.758  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.747  -2.517  -1.302  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.820  -1.565  -2.386  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.440   0.576   0.728  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.039  -1.420   0.891  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.186   0.729   1.644  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.015   2.391   0.371  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3    3    7
CONECT    3    4
CONECT    4    5    5   25
CONECT    5    6
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   26
CONECT   10   11
CONECT   11   12   21   27
CONECT   12   13
CONECT   13   14   20   28
CONECT   14   15   29   30
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   31
CONECT   19   20
CONECT   20   21   32
CONECT   21   22   33
CONECT   22   34
END

HMDB0000058
     RDKit          3D
Cyclic AMP
 34 37  0  0  0  0  0  0  0  0999 V2000
   -5.5227   -0.6321   -0.3239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383    0.3834   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955    1.6749   -0.0521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8168    2.5829    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5196    2.2089   -0.1413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796    0.9279   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.0044   -0.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6037   -1.1931   -0.6137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2797   -1.0026   -0.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9970    0.3020   -0.5194 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300    0.8986   -0.5315 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1164    0.2048   -1.4167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1170   -0.4331   -0.7427 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5350   -1.7481   -1.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.2229   -0.6589 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354   -1.2660    0.6107 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9025   -2.1625    1.5862 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2039   -0.0987    0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -0.5810    1.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.5439    0.6966 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9526    0.7730    0.8430 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8997    1.7497    1.0902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0411   -0.9024   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7528   -1.1545    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0840    3.6244    0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -1.8034   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2778    1.9886   -0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253    0.2270   -0.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -2.5166   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198   -1.5648   -2.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402    0.5759    0.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.4201    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856    0.7287    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145    2.3907    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  7  2  1  0
 21 11  1  0
 10  6  1  0
 20 13  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  6
 13 28  1  1
 14 29  1  0
 14 30  1  0
 18 31  1  0
 20 32  1  6
 21 33  1  1
 22 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Adenosine 3',5'-cyclic monophosphate	ChEBI
Adenosine 3',5'-cyclic phosphate	ChEBI
Adenosine 3',5'-phosphate	ChEBI
ADENOSINE-3',5'-cyclic-monophosphATE	ChEBI
CAMP	ChEBI
Cyclic adenylic acid	ChEBI
Adenosine 3',5'-cyclic monophosphoric acid	Generator
Adenosine 3',5'-cyclic phosphoric acid	Generator
Adenosine 3',5'-phosphoric acid	Generator
ADENOSINE-3',5'-cyclic-monophosphoric acid	Generator
Cyclic adenylate	Generator
3'5'-Cyclic AMP	HMDB
6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxide	HMDB
Acrasin	HMDB
Adenosine 3',5'-cyclophosphate	HMDB
Adenosine 3',5'-monophosphate	HMDB
Adenosine 3,5'-cyclic monophosphorate	HMDB
Adenosine 3,5'-cyclic monophosphoric acid	HMDB
Adenosine cyclic monophosphate	HMDB
Adenosine cyclic-monophosphate	HMDB
Adenosine-cyclic-phosphate	HMDB
Adenosine-cyclic-phosphoric-acid	HMDB
Cyclic 3',5'-adenylate	HMDB
Cyclic 3',5'-adenylic acid	HMDB
Cyclic 3',5'-AMP	HMDB
Cyclic adenosine 3',5'-phosphate	HMDB
3',5'-monoPhosphate, adenosine cyclic	HMDB
Cyclic AMP, disodium salt	HMDB
Cyclic AMP, monopotassium salt	HMDB
Cyclic AMP, sodium salt	HMDB
AMP, Cyclic	HMDB
Adenosine cyclic 3',5' monophosphate	HMDB
Adenosine cyclic-3',5'-monophosphate	HMDB
Cyclic AMP, (R)-isomer	HMDB
Cyclic AMP, monosodium salt	HMDB
Adenosine cyclic 3',5'-monophosphate	HMDB
monoPhosphate, adenosine cyclic	HMDB
Adenosine cyclic 3,5 monophosphate	HMDB
Cyclic 3',5'-monophosphate, adenosine	HMDB
Cyclic AMP, monoammonium salt	HMDB
Cyclic monophosphate, adenosine	HMDB
Cyclic-3',5'-monophosphate, adenosine	HMDB
Cyclic AMP	ChEBI

Chemical Formula

C₁₀H₁₂N₅O₆P

Average Molecular Weight

329.2059

Monoisotopic Molecular Weight

329.052519653

IUPAC Name

(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one

Traditional Name

(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one

CAS Registry Number

60-92-4

SMILES

[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N

InChI Identifier

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

InChI Key

IVOMOUWHDPKRLL-KQYNXXCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Cyclic purine nucleotides

Direct Parent

3',5'-cyclic purine nucleotides

Alternative Parents

Substituents

3',5'-cyclic purine ribonucleotide
Pentose phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Purine
Imidazopyrimidine
Aminopyrimidine
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Pyrimidine
Imidolactam
Imidazole
Azole
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3',5'-cyclic purine nucleotide (CHEBI:17489 )
adenyl ribonucleotide (CHEBI:17489 )
3',5'-Cyclic nuclcleotides (C00575 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	219 - 220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4 mg/mL	Not Available
LogP	-2.96	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	172.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000146
[M+H]+	Not Available	179.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000146

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.58 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	154.84 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.29 m³·mol⁻¹	ChemAxon
Polarizability	28.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.852	31661259
DarkChem	[M-H]-	167.324	31661259
AllCCS	[M+H]+	172.297	32859911
AllCCS	[M-H]-	167.092	32859911
DeepCCS	[M-2H]-	190.927	30932474
DeepCCS	[M+Na]+	165.915	30932474
AllCCS	[M+H]+	172.3	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	175.2	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	167.1	32859911
AllCCS	[M+Na-2H]-	166.4	32859911
AllCCS	[M+HCOO]-	165.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclic AMP	[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N	3561.4	Standard polar	33892256
Cyclic AMP	[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N	2774.1	Standard non polar	33892256
Cyclic AMP	[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N	3142.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclic AMP,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C(N)N=CN=C21	2963.2	Semi standard non polar	33892256
Cyclic AMP,1TMS,isomer #2	C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C(N)N=CN=C43)[C@H](O)[C@@H]2O1	2965.5	Semi standard non polar	33892256
Cyclic AMP,1TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O	3027.0	Semi standard non polar	33892256
Cyclic AMP,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N)N=CN=C21	2901.0	Semi standard non polar	33892256
Cyclic AMP,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N)N=CN=C21	2813.2	Standard non polar	33892256
Cyclic AMP,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N)N=CN=C21	4515.9	Standard polar	33892256
Cyclic AMP,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O[Si](C)(C)C	2954.5	Semi standard non polar	33892256
Cyclic AMP,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O[Si](C)(C)C	2862.0	Standard non polar	33892256
Cyclic AMP,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O[Si](C)(C)C	4731.3	Standard polar	33892256
Cyclic AMP,2TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C)O[C@H]2[C@H]1O	2961.6	Semi standard non polar	33892256
Cyclic AMP,2TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C)O[C@H]2[C@H]1O	2867.5	Standard non polar	33892256
Cyclic AMP,2TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C)O[C@H]2[C@H]1O	4395.6	Standard polar	33892256
Cyclic AMP,2TMS,isomer #4	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O)[Si](C)(C)C	2985.6	Semi standard non polar	33892256
Cyclic AMP,2TMS,isomer #4	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O)[Si](C)(C)C	2936.3	Standard non polar	33892256
Cyclic AMP,2TMS,isomer #4	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O)[Si](C)(C)C	4681.0	Standard polar	33892256
Cyclic AMP,3TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C)O[C@H]2[C@H]1O[Si](C)(C)C	2948.2	Semi standard non polar	33892256
Cyclic AMP,3TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C)O[C@H]2[C@H]1O[Si](C)(C)C	2901.9	Standard non polar	33892256
Cyclic AMP,3TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C)O[C@H]2[C@H]1O[Si](C)(C)C	4090.3	Standard polar	33892256
Cyclic AMP,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	2981.5	Semi standard non polar	33892256
Cyclic AMP,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	2955.2	Standard non polar	33892256
Cyclic AMP,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	4241.9	Standard polar	33892256
Cyclic AMP,3TMS,isomer #3	C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C43)[C@H](O)[C@@H]2O1	2982.1	Semi standard non polar	33892256
Cyclic AMP,3TMS,isomer #3	C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C43)[C@H](O)[C@@H]2O1	2959.3	Standard non polar	33892256
Cyclic AMP,3TMS,isomer #3	C[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C43)[C@H](O)[C@@H]2O1	3910.7	Standard polar	33892256
Cyclic AMP,4TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	3000.7	Semi standard non polar	33892256
Cyclic AMP,4TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	2968.4	Standard non polar	33892256
Cyclic AMP,4TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	3631.6	Standard polar	33892256
Cyclic AMP,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C(N)N=CN=C21	3186.7	Semi standard non polar	33892256
Cyclic AMP,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C(N)N=CN=C43)[C@H](O)[C@@H]2O1	3169.4	Semi standard non polar	33892256
Cyclic AMP,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O	3204.2	Semi standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N)N=CN=C21	3302.8	Semi standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N)N=CN=C21	3207.0	Standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N)N=CN=C21	4649.4	Standard polar	33892256
Cyclic AMP,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O[Si](C)(C)C(C)(C)C	3335.0	Semi standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O[Si](C)(C)C(C)(C)C	3279.0	Standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O[Si](C)(C)C(C)(C)C	4756.3	Standard polar	33892256
Cyclic AMP,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]2[C@H]1O	3295.9	Semi standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]2[C@H]1O	3242.1	Standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]2[C@H]1O	4501.2	Standard polar	33892256
Cyclic AMP,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O)[Si](C)(C)C(C)(C)C	3361.6	Semi standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O)[Si](C)(C)C(C)(C)C	3357.2	Standard non polar	33892256
Cyclic AMP,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O)[Si](C)(C)C(C)(C)C	4594.6	Standard polar	33892256
Cyclic AMP,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]2[C@H]1O[Si](C)(C)C(C)(C)C	3455.1	Semi standard non polar	33892256
Cyclic AMP,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]2[C@H]1O[Si](C)(C)C(C)(C)C	3458.1	Standard non polar	33892256
Cyclic AMP,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(=O)(O[Si](C)(C)C(C)(C)C)O[C@H]2[C@H]1O[Si](C)(C)C(C)(C)C	4284.7	Standard polar	33892256
Cyclic AMP,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	3493.0	Semi standard non polar	33892256
Cyclic AMP,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	3560.2	Standard non polar	33892256
Cyclic AMP,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	4298.4	Standard polar	33892256
Cyclic AMP,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C43)[C@H](O)[C@@H]2O1	3450.5	Semi standard non polar	33892256
Cyclic AMP,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C43)[C@H](O)[C@@H]2O1	3529.1	Standard non polar	33892256
Cyclic AMP,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)OC[C@H]2O[C@@H](N3C=NC4=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C43)[C@H](O)[C@@H]2O1	4062.8	Standard polar	33892256
Cyclic AMP,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	3626.8	Semi standard non polar	33892256
Cyclic AMP,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	3690.8	Standard non polar	33892256
Cyclic AMP,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]2OP(=O)(O[Si](C)(C)C(C)(C)C)OC[C@H]2O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	3893.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cyclic AMP GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclic AMP GC-MS (3 TMS)	splash10-03du-2971000000-c0200940e0e88308fbde	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclic AMP GC-EI-TOF (Non-derivatized)	splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cyclic AMP GC-MS (Non-derivatized)	splash10-03du-2971000000-c0200940e0e88308fbde	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclic AMP GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fbl-3901000000-b95501fad426dc61082f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclic AMP GC-MS (1 TMS) - 70eV, Positive	splash10-03y0-3922000000-7e84eb99b8248254daa6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclic AMP GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclic AMP GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclic AMP GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclic AMP GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclic AMP GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclic AMP GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-0009000000-02ee7f342f5c1bada389	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-004i-0009000000-a00a2165c3d37c4e1ef2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-004i-0109000000-7f48145f84828c2bbd5d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-001i-0119000000-d94a34a13521ae3d4692	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-0udi-0900000000-f10e1d70e30865424af6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-03dr-0629000000-bf4ec1094b7991c3633c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-03dr-0629000000-9736faaf70ec79d5bd03	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-001i-0109000000-6bf3784f4b710ce04a3e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-03dr-0629000000-3f5ea9ba1508e359ad80	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-03dr-0519000000-059e8569ee179529bf21	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-001i-0009000000-88dad10a362b1088849e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-004i-0509004000-bb02289fcd39ac1a203c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0a4i-1900000000-da49323734f24bf724d6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-001i-0900000000-a4e60131f41413b6fecf	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-004i-0009000000-98ee4e70689c06adc603	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-056r-0409005001-97fd793d1d14a84c3530	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0a4i-0900000000-1f2045ac2ff736aa80a2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-001i-0900000000-8bbb24702fa6ccd76268	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-004i-0009000000-6d23df7535894180e6df	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-001i-0009000000-c527aad341e122fc9bea	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOF	splash10-001i-0209000000-1bb2d660cc00c85a808f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyclic AMP LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-003r-2904000000-865c1b989665f73ac3f4	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclic AMP 10V, Positive-QTOF	splash10-000i-0904000000-f37dad1d4334840eb74e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclic AMP 20V, Positive-QTOF	splash10-000i-0900000000-8b2624b0c421f5f77e8e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclic AMP 40V, Positive-QTOF	splash10-000i-1900000000-3052962b6de42b1e2f5d	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Golgi apparatus

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

All Tissues
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Purine metabolism	Not Available
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available
Lesch-Nyhan Syndrome (LNS)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0085 +/- 0.0005 uM	Adult (>18 years old)	Both	Normal	15196297	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.020 +/- 0.004 uM	Adult (>18 years old)	Both	Normal	6326460	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.020+/- 0.004 uM	Adult (>18 years old)	Not Specified	Normal	6326460	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.024 (0.022-0.026) uM	Adult (>18 years old)	Both	Normal	12973949	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.021 +/- 0.008 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.020 (0.016-0.024) uM	Adult (>18 years old)	Both	Normal	6326460	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Urine	Detected and Quantified	0.38 +/- 0.14 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	8186443	details
Urine	Detected and Quantified	0.22 +/- 0.055 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	179127	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0077 +/- 0.0003 uM	Adult (>18 years old)	Male	Sildenafil-induced headache	15196297	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0110 +/- 0.0028 uM	Adult (>18 years old)	Both	Idiopathic polyneuritis	6326460	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.033 +/- 0.012 uM	Adult (>18 years old)	Not Specified	Meningitis	6326460	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00860 (0.00620-0.0110) uM	Adult (>18 years old)	Both	Hypoxic-ischemic encephalopathy	12973949	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.014 (0.012-0.017) uM	Adult (>18 years old)	Both	Hypoxic-ischemic encephalopathy	12973949	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0202 +/- 0.004 uM	Adult (>18 years old)	Not Specified	Initial slight suspicion of meningitis with normal CSF	6326460	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.034 (0.021-0.046) uM	Adult (>18 years old)	Both	Meningitis	6326460	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.011 (0.0082-0.014) uM	Adult (>18 years old)	Both	Idiopathic polyneuritis	6326460	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Urine	Detected and Quantified	0.24 +/- 0.028 umol/mmol creatinine	Adult (>18 years old)	Both	Chronic renal failure	9141788	details

Associated Disorders and Diseases

Disease References

Headache
Kruuse C, Frandsen E, Schifter S, Thomsen LL, Birk S, Olesen J: Plasma levels of cAMP, cGMP and CGRP in sildenafil-induced headache. Cephalalgia. 2004 Jul;24(7):547-53. [PubMed:15196297 ]
Idiopathic polyneuritis
Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75. [PubMed:6326460 ]
Hypoxic-ischemic encephalopathy
Liu H, Chang L, Chen Y, Xia S, Zhang X: Clinical implication of the changes of cAMP, TXA2 and PGI2 in CSF of asphyxiated newborns. J Huazhong Univ Sci Technolog Med Sci. 2003;23(2):195-7, 200. [PubMed:12973949 ]
Meningitis
Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75. [PubMed:6326460 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Chronic renal failure
Dimitrakov D, Kumchev E, Lyutakova E, Ledzhev I, Nikolov D, Tsekov V: Cyclic adenosine monophosphate (cAMP) levels in predialysis patients with chronic renal failure. Folia Med (Plovdiv). 1997;39(1):29-33. [PubMed:9141788 ]

Associated OMIM IDs

139393 (Idiopathic polyneuritis)
266600 (Crohn's disease)

External Links

DrugBank ID

DB02527

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17489

Food Biomarker Ontology

Not Available

VMH ID

CAMP

MarkerDB ID

MDB00000029

Good Scents ID

Not Available

References

Synthesis Reference

Genieser, H. G.; Butt, E.; Bottin, U.; Dostmann, W.; Jastorff, B. Synthesis of the 3',5'-cyclic phosphates from unprotected nucleosides. Synthesis (1989), (1), 53-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Imashuku S, Todo S, Nakajima F: [Intra-aortic prostaglandin E1 infusion in the treatment of advanced neuroblastoma]. Gan To Kagaku Ryoho. 1983 Sep;10(9):1936-43. [PubMed:6311112 ]
Wine JJ, Joo NS: Submucosal glands and airway defense. Proc Am Thorac Soc. 2004;1(1):47-53. [PubMed:16113412 ]
Onali P, Strada SJ, Chang L, Epstein PM, Hersh EM, Thompson WJ: Purification and characterization of high-affinity cyclic adenosine 5'-monophosphate phosphodiesterases from human acute myelogenous leukemic cells. Cancer Res. 1985 Mar;45(3):1384-91. [PubMed:2982489 ]
Rademaker MT, Charles CJ, Lewis LK, Yandle TG, Cooper GJ, Coy DH, Richards AM, Nicholls MG: Beneficial hemodynamic and renal effects of adrenomedullin in an ovine model of heart failure. Circulation. 1997 Sep 16;96(6):1983-90. [PubMed:9323090 ]
Mashayekhi F, Aghahoseini F, Rezaie A, Zamani MJ, Khorasani R, Abdollahi M: Alteration of cyclic nucleotides levels and oxidative stress in saliva of human subjects with periodontitis. J Contemp Dent Pract. 2005 Nov 15;6(4):46-53. [PubMed:16299606 ]
Sugo T, Tachimoto H, Chikatsu T, Murakami Y, Kikukawa Y, Sato S, Kikuchi K, Nagi T, Harada M, Ogi K, Ebisawa M, Mori M: Identification of a lysophosphatidylserine receptor on mast cells. Biochem Biophys Res Commun. 2006 Mar 24;341(4):1078-87. Epub 2006 Jan 25. [PubMed:16460680 ]
Watanabe K, Beinborn M, Nagamatsu S, Ishida H, Takahashi S: Menetrier's disease in a patient with Helicobacter pylori infection is linked to elevated glucagon-like peptide-2 activity. Scand J Gastroenterol. 2005 Apr;40(4):477-81. [PubMed:16028444 ]
Naef A, Keller HU: A short transient increase in cyclic adenosine 3', 5'-monophosphate levels of neutrophil granulocytes following exposure to chemotactic factors. Adv Exp Med Biol. 1982;141:39-48. [PubMed:6283833 ]
Kukreja SC, Shevrin DH, Wimbiscus SA, Ebeling PR, Danks JA, Rodda CP, Wood WI, Martin TJ: Antibodies to parathyroid hormone-related protein lower serum calcium in athymic mouse models of malignancy-associated hypercalcemia due to human tumors. J Clin Invest. 1988 Nov;82(5):1798-802. [PubMed:2846659 ]
Wickenheisser JK, Nelson-DeGrave VL, McAllister JM: Human ovarian theca cells in culture. Trends Endocrinol Metab. 2006 Mar;17(2):65-71. Epub 2006 Feb 7. [PubMed:16460956 ]
Fouassier L, Chinet T, Robert B, Carayon A, Balladur P, Mergey M, Paul A, Poupon R, Capeau J, Barbu V, Housset C: Endothelin-1 is synthesized and inhibits cyclic adenosine monophosphate- dependent anion secretion by an autocrine/paracrine mechanism in gallbladder epithelial cells. J Clin Invest. 1998 Jun 15;101(12):2881-8. [PubMed:9637723 ]
Carceles MD, Ribo AR, Davalos R, Martinez T, Hernandez J: Effect of diazepam on adenosine 3',5'-cyclic monophosphate (cAMP) plasma levels in anesthetized patients. Clin Ther. 2004 May;26(5):737-43. [PubMed:15220017 ]
Chu MS, Chang CF, Yang CC, Bau YC, Ho LL, Hung SC: Signalling pathway in the induction of neurite outgrowth in human mesenchymal stem cells. Cell Signal. 2006 Apr;18(4):519-30. Epub 2005 Aug 11. [PubMed:16098715 ]
Rudman D, O'Brien MS, McKinney AS, Hoffman JC Jr, Patterson JH: Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid. J Clin Endocrinol Metab. 1976 Jun;42(6):1088-97. [PubMed:180045 ]
Machen TE: Innate immune response in CF airway epithelia: hyperinflammatory? Am J Physiol Cell Physiol. 2006 Aug;291(2):C218-30. [PubMed:16825601 ]
Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75. [PubMed:6326460 ]
Ruppert D, Weithmann KU: HL 725, an extremely potent inhibitor of platelet phosphodiesterase and induced platelet aggregation in vitro. Life Sci. 1982 Nov 8;31(19):2037-43. [PubMed:6294426 ]
Tanaka Y, Horinouchi T, Koike K: New insights into beta-adrenoceptors in smooth muscle: distribution of receptor subtypes and molecular mechanisms triggering muscle relaxation. Clin Exp Pharmacol Physiol. 2005 Jul;32(7):503-14. [PubMed:16026507 ]
Fischer JA, Bourne HR, Dambacher MA, Tschopp F, De Meyer R, Devogelaer JP, Werder EA, Nagant De Deuxchaisnes C: Pseudohypoparathyroidism: inheritance and expression of deficient receptor-cyclase coupling protein activity. Clin Endocrinol (Oxf). 1983 Dec;19(6):747-54. [PubMed:6317236 ]
Liu H, Chang L, Chen Y, Xia S, Zhang X: Clinical implication of the changes of cAMP, TXA2 and PGI2 in CSF of asphyxiated newborns. J Huazhong Univ Sci Technolog Med Sci. 2003;23(2):195-7, 200. [PubMed:12973949 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 165 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Histone acetyltransferase p300

General function:: Involved in transcription cofactor activity
Specific function:: Functions as histone acetyltransferase and regulates transcription via chromatin remodeling. Acetylates all four core histones in nucleosomes. Histone acetylation gives an epigenetic tag for transcriptional activation. Mediates cAMP-gene regulation by binding specifically to phosphorylated CREB protein. Also functions as acetyltransferase for nonhistone targets. Acetylates 'Lys-131' of ALX1 and acts as its coactivator in the presence of CREBBP. Acetylates SIRT2 and is proposed to indirectly increase the transcriptional activity of TP53 through acetylation and subsequent attenuation of SIRT2 deacetylase function. Acetylates HDAC1 leading to its inactivation and modulation of transcription. Acts as a TFAP2A-mediated transcriptional coactivator in presence of CITED2. Plays a role as a coactivator of NEUROD1-dependent transcription of the secretin and p21 genes and controls terminal differentiation of cells in the intestinal epithelium. Promotes cardiac myocyte enlargement. Can also mediate transcriptional repression. Binds to and may be involved in the transforming capacity of the adenovirus E1A protein. In case of HIV-1 infection, it is recruited by the viral protein Tat. Regulates Tat's transactivating activity and may help inducing chromatin remodeling of proviral genes. Acetylates FOXO1 and enhances its transcriptional activity.
Gene Name:: EP300
Uniprot ID:: Q09472
Molecular weight:: 264159.725

Enzyme Details

2. CREB-binding protein

General function:: Involved in transcription cofactor activity
Specific function:: Acetylates histones, giving a specific tag for transcriptional activation. Also acetylates non-histone proteins, like NCOA3 and FOXO1. Binds specifically to phosphorylated CREB and enhances its transcriptional activity toward cAMP-responsive genes. Acts as a coactivator of ALX1 in the presence of EP300.
Gene Name:: CREBBP
Uniprot ID:: Q92793
Molecular weight:: 260991.825

Enzyme Details

3. Ectonucleotide pyrophosphatase/phosphodiesterase family member 1

General function:: Involved in catalytic activity
Specific function:: Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:: ENPP1
Uniprot ID:: P22413
Molecular weight:: 104923.58

Enzyme Details

4. Hormone-sensitive lipase

General function:: Involved in hydrolase activity
Specific function:: In adipose tissue and heart, it primarily hydrolyzes stored triglycerides to free fatty acids, while in steroidogenic tissues, it principally converts cholesteryl esters to free cholesterol for steroid hormone production.
Gene Name:: LIPE
Uniprot ID:: Q05469
Molecular weight:: 116596.715

Enzyme Details

5. Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:: PDE6H
Uniprot ID:: Q13956
Molecular weight:: 9074.36

Enzyme Details

6. Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a higher affinity for cGMP than for cAMP.
Gene Name:: PDE1A
Uniprot ID:: P54750
Molecular weight:: 61251.38

Reactions

Cyclic AMP + Water → Adenosine monophosphate	details

Enzyme Details

7. High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in maintaining basal levels of the cyclic nucleotide and/or in the cAMP regulation of germ cell development.
Gene Name:: PDE8A
Uniprot ID:: O60658
Molecular weight:: 86047.88

Reactions

Cyclic AMP + Water → Adenosine monophosphate	details

Enzyme Details

8. Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a preference for cGMP as a substrate.
Gene Name:: PDE1B
Uniprot ID:: Q01064
Molecular weight:: 61379.235

Reactions

Cyclic AMP + Water → Adenosine monophosphate	details

Enzyme Details

9. cGMP-inhibited 3',5'-cyclic phosphodiesterase B

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. May play a role in fat metabolism. Regulates cAMP binding of RAPGEF3. Through simultaneous binding to RAPGEF3 and PIK3R6 assembles a signaling complex in which the PI3K gamma complex is activated by RAPGEF3 and which is involved in angiogenesis.
Gene Name:: PDE3B
Uniprot ID:: Q13370
Molecular weight:: 124332.145

Reactions

Cyclic AMP + Water → Adenosine monophosphate	details

Enzyme Details

10. High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A

General function:: Involved in 3',5'-cyclic-AMP phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May have a role in muscle signal transduction.
Gene Name:: PDE7A
Uniprot ID:: Q13946
Molecular weight:: 55504.475

Reactions

Cyclic AMP + Water → Adenosine monophosphate	details

Transporters

Enzyme Details

1. Sodium bicarbonate cotransporter 3

General function:: Involved in anion transport
Specific function:: Electroneutral sodium- and bicarbonate-dependent cotransporter with a Na(+):HCO3(-) 1:1 stoichiometry. Regulates intracellular pH and may play a role in bicarbonate salvage in secretory epithelia. May also have an associated sodium channel activity.
Gene Name:: SLC4A7
Uniprot ID:: Q9Y6M7
Molecular weight:: 127358.16

Enzyme Details

2. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Chen ZS, Lee K, Kruh GD: Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine. J Biol Chem. 2001 Sep 7;276(36):33747-54. Epub 2001 Jul 10. [PubMed:11447229 ]
van Aubel RA, Smeets PH, Peters JG, Bindels RJ, Russel FG: The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP. J Am Soc Nephrol. 2002 Mar;13(3):595-603. [PubMed:11856762 ]
Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, Kruh GD: Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res. 2002 Jun 1;62(11):3144-50. [PubMed:12036927 ]
Lai L, Tan TM: Role of glutathione in the multidrug resistance protein 4 (MRP4/ABCC4)-mediated efflux of cAMP and resistance to purine analogues. Biochem J. 2002 Feb 1;361(Pt 3):497-503. [PubMed:11802779 ]

Enzyme Details

3. Multidrug resistance-associated protein 5

General function:: Involved in ATP binding
Specific function:: Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:: ABCC5
Uniprot ID:: O15440
Molecular weight:: 160658.8

References

Jedlitschky G, Burchell B, Keppler D: The multidrug resistance protein 5 functions as an ATP-dependent export pump for cyclic nucleotides. J Biol Chem. 2000 Sep 29;275(39):30069-74. [PubMed:10893247 ]

Enzyme Details

4. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [PubMed:9228014 ]

Enzyme Details

5. ATP-binding cassette sub-family C member 11

General function:: Involved in ATP binding
Specific function:: Participates in physiological processes involving bile acids, conjugated steroids and cyclic nucleotides. Enhances the cellular extrusion of cAMP and cGMP. Stimulates the ATP-dependent uptake of a range of physiological and synthetic lipophilic anions, including the glutathione S-conjugates leukotriene C4 and dinitrophenyl S-glutathione, steroid sulfates such as dehydroepiandrosterone 3-sulfate (DHEAS) and estrone 3-sulfate, glucuronides such as estradiol 17-beta-D-glucuronide (E(2)17betaG), the monoanionic bile acids glycocholate and taurocholate, and methotrexate. Probably functions to secrete earwax
Gene Name:: ABCC11
Uniprot ID:: Q96J66
Molecular weight:: 154299.6

References

Chen ZS, Guo Y, Belinsky MG, Kotova E, Kruh GD: Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11). Mol Pharmacol. 2005 Feb;67(2):545-57. Epub 2004 Nov 10. [PubMed:15537867 ]
Guo Y, Kotova E, Chen ZS, Lee K, Hopper-Borge E, Belinsky MG, Kruh GD: MRP8, ATP-binding cassette C11 (ABCC11), is a cyclic nucleotide efflux pump and a resistance factor for fluoropyrimidines 2',3'-dideoxycytidine and 9'-(2'-phosphonylmethoxyethyl)adenine. J Biol Chem. 2003 Aug 8;278(32):29509-14. Epub 2003 May 22. [PubMed:12764137 ]

Enzyme Details

6. Solute carrier organic anion transporter family member 4C1

General function:: Involved in transporter activity
Specific function:: Organic anion transporter, capable of transporting pharmacological substances such as digoxin, ouabain, thyroxine, methotrexate and cAMP. May participate in the regulation of membrane transport of ouabain. Involved in the uptake of the dipeptidyl peptidase-4 inhibitor sitagliptin and hence may play a role in its transport into and out of renal proximal tubule cells. May be involved in the first step of the transport pathway of digoxin and various compounds into the urine in the kidney. May be involved in sperm maturation by enabling directed movement of organic anions and compounds within or between cells. This ion- transporting process is important to maintain the strict epididymal homeostasis necessary for sperm maturation. May have a role in secretory functions since seminal vesicle epithelial cells are assumed to secrete proteins involved in decapacitation by modifying surface proteins to facilitate the acquisition of the ability to fertilize the egg
Gene Name:: SLCO4C1
Uniprot ID:: Q6ZQN7
Molecular weight:: 78947.5

Enzyme Details

7. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Sun W, Wu RR, van Poelje PD, Erion MD: Isolation of a family of organic anion transporters from human liver and kidney. Biochem Biophys Res Commun. 2001 May 4;283(2):417-22. [PubMed:11327718 ]

Only showing the first 10 proteins. There are 165 proteins in total.

Show all enzymes and transporters

Showing metabocard for Cyclic AMP (HMDB0000058)

MOL for HMDB0000058 (Cyclic AMP)

3D MOL for HMDB0000058 (Cyclic AMP)

3D SDF for HMDB0000058 (Cyclic AMP)

3D-SDF for HMDB0000058 (Cyclic AMP)

PDB for HMDB0000058 (Cyclic AMP)

3D PDB for HMDB0000058 (Cyclic AMP)

SMILES for HMDB0000058 (Cyclic AMP)

INCHI for HMDB0000058 (Cyclic AMP)

Structure for HMDB0000058 (Cyclic AMP)

3D Structure for HMDB0000058 (Cyclic AMP)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

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Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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Transporters

References

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