NP-MRD: Showing NP-Card for Cyclic AMP (NP0000123)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:39:01 UTC

NP-MRD ID

NP0000123

Secondary Accession Numbers

None

Natural Product 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>
NP0000123

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

329.2059 Da

Monoisotopic Mass

329.05252 Da

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

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daucus carota	Plant	KNApSAcK
Dimocarpus longan	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Nicotiana tabacum	Plant	KNApSAcK
Pelargonium sidoides	LOTUS Database	35616633
Phaseolus vulgaris	Plant	KNApSAcK
Pisum sativum	LOTUS Database	35616633
Secale cereale	LOTUS Database	35616633
Streptomyces hygroscopicus	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted 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

External Links

HMDB ID

HMDB0000058

DrugBank ID

DB02527

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1136631

References

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 ]

Showing NP-Card for Cyclic AMP (NP0000123)

MOL for NP0000123 (Cyclic AMP)

3D MOL for NP0000123 (Cyclic AMP)

3D SDF for NP0000123 (Cyclic AMP)

3D-SDF for NP0000123 (Cyclic AMP)

PDB for NP0000123 (Cyclic AMP)

3D PDB for NP0000123 (Cyclic AMP)

SMILES for NP0000123 (Cyclic AMP)

INCHI for NP0000123 (Cyclic AMP)

Structure for NP0000123 (Cyclic AMP)

3D Structure for NP0000123 (Cyclic AMP)