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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-01-29 15:28:58 UTC

Update Date

2022-09-22 17:43:58 UTC

HMDB ID

HMDB0011616

Secondary Accession Numbers

HMDB11616

Metabolite Identification

Common Name

Adenosine 2',3'-cyclic phosphate

Description

Sedoheptulose, also known as D-altro-heptulose or volemulose, belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. The Crassulaceae, or orpine family, is a family of dicotyledons. Sedoheptulose is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, sedoheptulose is involved in pentose phosphate pathway. They are found worldwide, but mostly occur in the northern hemisphere and southern Africa, typically in dry and/or cold areas where water may be scarce. It also plays an important role as a transitory compound in the cyclic regeneration of D-ribulose for carbon dioxide fixation in plant photosynthesis. Sedoheptulose is a seven-carbon ketose sugar originally found in Sedum spectabile, a common perennial garden plant. As a result, this sugar is often found to be part of the human diet. It is one of the few heptoses found in nature. Later it was shown to be widely distributed in the plants of the Crassulaceae family. The family includes about 1,400 species in 33 genera.

Structure

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

HMDB0011616
     RDKit          3D
Adenosine 2',3'-cyclic phosphate
 34 37  0  0  0  0  0  0  0  0999 V2000
    5.1782   -0.1727   -1.4070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832   -0.6957   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0066   -1.9836   -0.3061 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.4366    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -1.5982    0.7030 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349   -0.3079    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222    0.1576   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8002    1.4660   -0.5794 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6063    1.7849   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0649    0.6895    0.5467 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141    0.6859    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6613   -0.6316    1.2725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -0.5469    1.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -1.8929    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0021   -1.8452    1.2220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4039    0.5175    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6358    0.0386   -0.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460    1.3703   -1.7689 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.6405    0.9690   -3.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3884    2.5086   -1.8439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146    1.9153   -0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768    1.4418    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7197    0.6330   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484   -0.6203   -2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304   -3.4594    0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1704    2.7664   -0.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    1.0289    2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485   -0.2333    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136   -2.1519    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -2.6879    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274   -2.7960    1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3548    1.0173    0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406    2.7463   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501    2.3230    1.1287 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
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END


  Mrv0541 02241201472D          

 22 25  0  0  1  0            999 V2000
   14.1400   -5.3913    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.3195   -5.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1400   -4.5663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8044   -6.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0811   -5.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6686   -5.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9061   -5.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0811   -4.3228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3186   -5.0372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9061   -4.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5291   -6.3648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7753   -6.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8616   -5.2087    0.0000 N   0  0  1  0  0  0  0  0  0  0  0  0
   16.1942   -4.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1942   -3.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4095   -4.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9246   -4.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4095   -3.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2380   -2.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4533   -2.5819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3186   -6.4662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9246   -5.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
  6  5  2  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 13  6  1  0  0  0  0
 13 14  1  1  0  0  0
 16 14  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 21  7  1  0  0  0  0
  3 17  1  0  0  0  0
 22  1  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011616

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(O)(=O)OC12

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)

> <INCHI_KEY>
KMYWVDDIPVNLME-UHFFFAOYSA-N

> <FORMULA>
C10H12N5O6P

> <MOLECULAR_WEIGHT>
329.2059

> <EXACT_MASS>
329.052519653

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
28.375450838587973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one

> <ALOGPS_LOGP>
-2.51

> <JCHEM_LOGP>
-3.8298289107849044

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.584307323434835

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7592537911346091

> <JCHEM_PKA_STRONGEST_BASIC>
4.9887015214332004

> <JCHEM_POLAR_SURFACE_AREA>
154.84

> <JCHEM_REFRACTIVITY>
70.2895

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(6-aminopurin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011616
     RDKit          3D
Adenosine 2',3'-cyclic phosphate
 34 37  0  0  0  0  0  0  0  0999 V2000
    5.1782   -0.1727   -1.4070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832   -0.6957   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0066   -1.9836   -0.3061 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.4366    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -1.5982    0.7030 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349   -0.3079    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222    0.1576   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8002    1.4660   -0.5794 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6063    1.7849   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0649    0.6895    0.5467 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141    0.6859    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6613   -0.6316    1.2725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -0.5469    1.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -1.8929    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0021   -1.8452    1.2220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4039    0.5175    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6358    0.0386   -0.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460    1.3703   -1.7689 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.6405    0.9690   -3.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3884    2.5086   -1.8439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146    1.9153   -0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768    1.4418    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7197    0.6330   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484   -0.6203   -2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304   -3.4594    0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1704    2.7664   -0.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    1.0289    2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485   -0.2333    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136   -2.1519    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -2.6879    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274   -2.7960    1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3548    1.0173    0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406    2.7463   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501    2.3230    1.1287 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
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  P   UNK     0      26.395 -10.064   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      24.863 -10.225   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      26.395  -8.524   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      25.768 -11.471   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      33.751 -10.737   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.981  -9.403   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.291 -10.737   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      33.751  -8.069   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      36.061  -9.403   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      35.291  -8.069   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      32.721 -11.881   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      31.314 -11.255   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      31.475  -9.723   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      30.229  -8.818   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      30.229  -7.278   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      28.764  -9.294   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.859  -8.048   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.764  -6.802   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.444  -5.296   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      26.979  -4.820   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      36.061 -12.070   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      27.859 -10.540   0.000  0.00  0.00           O+0
CONECT    1    2    3    4   22                                             
CONECT    2    1                                                            
CONECT    3    1   17                                                       
CONECT    4    1                                                            
CONECT    5    7   11    6                                                  
CONECT    6    8    5   13                                                  
CONECT    7    5    9   21                                                  
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    8    9                                                       
CONECT   11    5   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   18                                                       
CONECT   16   14   17   22                                                  
CONECT   17   16   18    3                                                  
CONECT   18   15   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    7                                                            
CONECT   22    1   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0011616
HETATM    1  N1  UNL     1       5.178  -0.173  -1.407  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.083  -0.696  -0.688  1.00  0.00           C  
HETATM    3  N2  UNL     1       4.007  -1.984  -0.306  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.942  -2.437   0.379  1.00  0.00           C  
HETATM    5  N3  UNL     1       1.912  -1.598   0.703  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.935  -0.308   0.349  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.022   0.158  -0.351  1.00  0.00           C  
HETATM    8  N4  UNL     1       2.800   1.466  -0.579  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.606   1.785  -0.030  1.00  0.00           C  
HETATM   10  N5  UNL     1       1.065   0.689   0.547  1.00  0.00           N  
HETATM   11  C6  UNL     1      -0.214   0.686   1.226  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.661  -0.632   1.272  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.037  -0.547   1.431  1.00  0.00           C  
HETATM   14  C8  UNL     1      -2.617  -1.893   1.073  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.002  -1.845   1.222  1.00  0.00           O  
HETATM   16  C9  UNL     1      -2.404   0.518   0.429  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.636   0.039  -0.825  1.00  0.00           O  
HETATM   18  P1  UNL     1      -2.146   1.370  -1.769  1.00  0.00           P  
HETATM   19  O4  UNL     1      -1.640   0.969  -3.104  1.00  0.00           O  
HETATM   20  O5  UNL     1      -3.388   2.509  -1.844  1.00  0.00           O  
HETATM   21  O6  UNL     1      -0.915   1.915  -0.735  1.00  0.00           O  
HETATM   22  C10 UNL     1      -1.277   1.442   0.477  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.720   0.633  -1.061  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.448  -0.620  -2.324  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.830  -3.459   0.709  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.170   2.766  -0.059  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.101   1.029   2.284  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.249  -0.233   2.454  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.314  -2.152   0.048  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.246  -2.688   1.750  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.327  -2.796   1.150  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.355   1.017   0.779  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.641   2.746  -0.918  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.550   2.323   1.129  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   22   27
CONECT   12   13
CONECT   13   14   16   28
CONECT   14   15   29   30
CONECT   15   31
CONECT   16   17   22   32
CONECT   17   18
CONECT   18   19   19   20   21
CONECT   20   33
CONECT   21   22
CONECT   22   34
END

HMDB0011616
     RDKit          3D
Adenosine 2',3'-cyclic phosphate
 34 37  0  0  0  0  0  0  0  0999 V2000
    5.1782   -0.1727   -1.4070 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832   -0.6957   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0066   -1.9836   -0.3061 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.4366    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9120   -1.5982    0.7030 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9349   -0.3079    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222    0.1576   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8002    1.4660   -0.5794 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6063    1.7849   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0649    0.6895    0.5467 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141    0.6859    1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6613   -0.6316    1.2725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -0.5469    1.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -1.8929    1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0021   -1.8452    1.2220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4039    0.5175    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6358    0.0386   -0.8253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460    1.3703   -1.7689 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.6405    0.9690   -3.1042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3884    2.5086   -1.8439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146    1.9153   -0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768    1.4418    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7197    0.6330   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484   -0.6203   -2.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304   -3.4594    0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1704    2.7664   -0.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    1.0289    2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485   -0.2333    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136   -2.1519    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -2.6879    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274   -2.7960    1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3548    1.0173    0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406    2.7463   -0.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501    2.3230    1.1287 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
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
beta-D-Sedoheptulose	ChEBI
D-Altro-heptulose	ChEBI
D-Sedoheptulose	ChEBI
Volemulose	ChEBI
b-D-Sedoheptulose	Generator
Β-D-sedoheptulose	Generator
b-D-Sedoheptulopyranose	HMDB
Β-D-sedoheptulopyranose	HMDB
D-Altroheptulose	HMDB
beta-D-Sedoheptulopyranose	HMDB
beta-D-Altro-2-heptulopyranose	HMDB
Β-D-altro-2-heptulopyranose	HMDB
2',3'-CAMP	HMDB
2',3'-Cyclic adenosine monophosphate	HMDB
Adenosine cyclic 2',3'-monophosphate	HMDB
Cyclic 2',3'-(hydrogen phosphate)-adenosine	HMDB
Cyclic 2',3'-AMP	HMDB
2',3'-Cyclic AMP	MeSH, HMDB
2',3'-Cyclic AMP, monosodium salt	MeSH, HMDB
Adenosine cyclic-2',3'-monophosphate	MeSH, HMDB
2',3'-Cyclic AMP, sodium salt	MeSH, HMDB
Adenosine cyclic 2,3 monophosphate	MeSH, HMDB
Adenosine 2',3'-cyclic phosphoric acid	Generator

Chemical Formula

C₁₀H₁₂N₅O₆P

Average Molecular Weight

329.2059

Monoisotopic Molecular Weight

329.052519653

IUPAC Name

4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one

Traditional Name

4-(6-aminopurin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one

CAS Registry Number

634-01-5

SMILES

NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(O)(=O)OC12

InChI Identifier

InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)

InChI Key

KMYWVDDIPVNLME-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
C-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

sedoheptulose (CHEBI:27520 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.59 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.76	ChemAxon
pKa (Strongest Basic)	4.99	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	2	ChemAxon
Refractivity	70.29 m³·mol⁻¹	ChemAxon
Polarizability	28.38 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]+	173.161	31661259
DarkChem	[M-H]-	172.462	31661259
DeepCCS	[M-2H]-	188.125	30932474
DeepCCS	[M+Na]+	164.291	30932474
AllCCS	[M+H]+	173.0	32859911
AllCCS	[M+H-H2O]+	169.8	32859911
AllCCS	[M+NH4]+	176.0	32859911
AllCCS	[M+Na]+	176.9	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adenosine 2',3'-cyclic phosphate	NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(O)(=O)OC12	3700.8	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate	NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(O)(=O)OC12	2630.6	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate	NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(O)(=O)OC12	3247.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adenosine 2',3'-cyclic phosphate,1TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=NC3=C(N)N=CN=C32)C2OP(=O)(O)OC12	3046.3	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,1TMS,isomer #2	C[Si](C)(C)OP1(=O)OC2C(CO)OC(N3C=NC4=C(N)N=CN=C43)C2O1	3060.3	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,1TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O)OC21	3070.2	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=NC3=C(N)N=CN=C32)C2OP(=O)(O[Si](C)(C)C)OC12	3018.1	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=NC3=C(N)N=CN=C32)C2OP(=O)(O[Si](C)(C)C)OC12	3085.7	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=NC3=C(N)N=CN=C32)C2OP(=O)(O[Si](C)(C)C)OC12	4434.8	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)C2OP(=O)(O)OC21	3045.3	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)C2OP(=O)(O)OC21	3018.0	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)C2OP(=O)(O)OC21	4678.1	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O[Si](C)(C)C)OC21	3048.8	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O[Si](C)(C)C)OC21	3074.1	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O[Si](C)(C)C)OC21	4484.1	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #4	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O)OC21)[Si](C)(C)C	3045.9	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #4	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O)OC21)[Si](C)(C)C	3154.2	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TMS,isomer #4	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O)OC21)[Si](C)(C)C	4680.0	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)C2OP(=O)(O[Si](C)(C)C)OC21	3034.7	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)C2OP(=O)(O[Si](C)(C)C)OC21	3067.3	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)C2OP(=O)(O[Si](C)(C)C)OC21	4203.6	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #2	C[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C2OP(=O)(O)OC12	3029.1	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #2	C[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C2OP(=O)(O)OC12	3164.6	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #2	C[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C2OP(=O)(O)OC12	4281.3	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #3	C[Si](C)(C)OP1(=O)OC2C(CO)OC(N3C=NC4=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C43)C2O1	3058.9	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #3	C[Si](C)(C)OP1(=O)OC2C(CO)OC(N3C=NC4=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C43)C2O1	3206.5	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TMS,isomer #3	C[Si](C)(C)OP1(=O)OC2C(CO)OC(N3C=NC4=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C43)C2O1	4083.7	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C2OP(=O)(O[Si](C)(C)C)OC12	3080.0	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C2OP(=O)(O[Si](C)(C)C)OC12	3199.8	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C2OP(=O)(O[Si](C)(C)C)OC12	3823.1	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N)N=CN=C32)C2OP(=O)(O)OC12	3260.3	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP1(=O)OC2C(CO)OC(N3C=NC4=C(N)N=CN=C43)C2O1	3264.8	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O)OC21	3254.0	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N)N=CN=C32)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC12	3427.8	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N)N=CN=C32)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC12	3538.8	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N)N=CN=C32)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC12	4595.7	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)C2OP(=O)(O)OC21	3441.4	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)C2OP(=O)(O)OC21	3488.4	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)C2OP(=O)(O)OC21	4761.4	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC21	3430.8	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC21	3500.8	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC21	4625.9	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O)OC21)[Si](C)(C)C(C)(C)C	3412.7	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O)OC21)[Si](C)(C)C(C)(C)C	3573.2	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2C1OC(CO)C2OP(=O)(O)OC21)[Si](C)(C)C(C)(C)C	4641.7	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC21	3571.0	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC21	3708.7	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC21	4457.6	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)C2OP(=O)(O)OC12	3562.7	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)C2OP(=O)(O)OC12	3813.0	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)C2OP(=O)(O)OC12	4405.9	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)OC2C(CO)OC(N3C=NC4=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C43)C2O1	3560.7	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)OC2C(CO)OC(N3C=NC4=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C43)C2O1	3804.0	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP1(=O)OC2C(CO)OC(N3C=NC4=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C43)C2O1	4258.4	Standard polar	33892256
Adenosine 2',3'-cyclic phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC12	3690.1	Semi standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC12	4001.8	Standard non polar	33892256
Adenosine 2',3'-cyclic phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)C2OP(=O)(O[Si](C)(C)C(C)(C)C)OC12	4077.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine 2',3'-cyclic phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00sl-4931000000-63bbe1c23904369ab6dc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine 2',3'-cyclic phosphate GC-MS (1 TMS) - 70eV, Positive	splash10-00di-4963000000-2b49ded7864dfe43fd63	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine 2',3'-cyclic phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine 2',3'-cyclic phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 10V, Positive-QTOF	splash10-000i-1904000000-0a4c1fe6e7f0f0e471dd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 20V, Positive-QTOF	splash10-000i-0900000000-28f1776c8c08029a9982	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 40V, Positive-QTOF	splash10-000i-2900000000-a28e89ce894806596ddd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 10V, Negative-QTOF	splash10-0059-0409000000-3004bf80483487c032f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 20V, Negative-QTOF	splash10-001i-0900000000-21e625f749ef75779625	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 40V, Negative-QTOF	splash10-053r-3900000000-4ed31a0af1579b8f5e05	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 10V, Positive-QTOF	splash10-001i-0009000000-a6a397633559c6672b08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 20V, Positive-QTOF	splash10-001i-0209000000-eb0e5bb1205894657ee7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 40V, Positive-QTOF	splash10-000i-0902000000-b0c38d2925719c58ec19	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 10V, Negative-QTOF	splash10-004i-0009000000-24546b3fc8282cbfee15	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 20V, Negative-QTOF	splash10-004i-0109000000-c2871eb4df0f5c053bf6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adenosine 2',3'-cyclic phosphate 40V, Negative-QTOF	splash10-053r-2900000000-d02a1a43356a83f68581	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.026 +/- 0.00096 uM	Adult (>18 years old)	Both	Normal	8186443	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001132

Chemspider ID

390207

KEGG Compound ID

C08355

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sedoheptulose

METLIN ID

Not Available

PubChem Compound

441483

PDB ID

Not Available

ChEBI ID

27520

Food Biomarker Ontology

Not Available

VMH ID

M03165

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Krall JF, Swensen JL, Korenman SG: Hormonal control of uterine contraction. Characterization od cyclic AMP-dependent membrane properties in the myometrium. Biochim Biophys Acta. 1976 Nov 2;448(4):578-88. [PubMed:184841 ]
Schoffstall AM: Prebiotic phosphorylation of nucleosides in formamide. Orig Life. 1976 Dec;7(4):399-412. [PubMed:1023139 ]
Cheng C, Fan C, Wan R, Tong C, Miao Z, Chen J, Zhao Y: Phosphorylation of adenosine with trimetaphosphate under simulated prebiotic conditions. Orig Life Evol Biosph. 2002 Jun;32(3):219-24. [PubMed:12227426 ]
Ghandour MS, Derer P, Labourdette G, Delaunoy JP, Langley OK: Glial cell markers in the reeler mutant mouse: a biochemical and immunohistological study. J Neurochem. 1981 Jan;36(1):195-200. [PubMed:6257845 ]
Wells MR, Sprinkle TJ: Purification of rat 2',3'-cyclic nucleotide 3'-phosphodiesterase. J Neurochem. 1981 Feb;36(2):633-9. [PubMed:6257858 ]
Reddy NB, Askanas V, Engel WK: Demonstration of 2',3'-cyclic nucleotide 3'-phosphohydrolase in cultured human Schwann cells. J Neurochem. 1982 Sep;39(3):887-9. [PubMed:6284879 ]
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 ]

Enzymes

Enzyme Details

1. 2',3'-cyclic-nucleotide 3'-phosphodiesterase

General function:: Involved in 2',3'-cyclic-nucleotide 3'-phosphodiesterase activity
Specific function:: May participate in RNA metabolism in the myelinating cell, CNP is the third most abundant protein in central nervous system myelin (By similarity).
Gene Name:: CNP
Uniprot ID:: P09543
Molecular weight:: 47578.22

Showing metabocard for Adenosine 2',3'-cyclic phosphate (HMDB0011616)

MOL for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

3D MOL for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

3D SDF for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

3D-SDF for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

PDB for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

3D PDB for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

SMILES for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

INCHI for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

Structure for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

3D Structure for HMDB0011616 (Adenosine 2',3'-cyclic phosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes