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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 23:00:45 UTC

Update Date

2022-11-23 22:29:22 UTC

HMDB ID

HMDB0259987

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Zaprinast

Description

5-(2-propoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol belongs to the class of organic compounds known as triazolopyrimidines. These are polycyclic aromatic compounds containing triazole ring fused to a pyrimidine ring. Triazole is a five-membered ring consisting of two carbon atoms and three nitrogen atoms. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Based on a literature review very few articles have been published on 5-(2-propoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Zaprinast is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Zaprinast is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259987
     RDKit          3D
zaprinast
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.9479   -2.2768    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -1.1701    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403   -1.2701   -0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -0.3609   -0.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8403    0.9677   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360    1.7922   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766    3.1679   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5131    3.7244   -0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    2.9096   -0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4114    1.5469   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    0.6988   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394    1.2239   -0.4101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9698    0.5054   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2402    1.0905   -0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038   -0.8558   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -1.8633   -0.0959 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787   -2.9802    0.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -2.7254   -0.0166 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -1.4000   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4679   -0.6196   -0.2308 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6232   -2.0927    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107   -2.2318    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363   -3.2523    0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597   -1.3671    1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -0.2477    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -2.3387   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734   -1.1531   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    1.4373   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    3.7927   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174    4.8049   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736    3.3604   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0248    0.6386   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9359   -3.4558    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 11  1  0
 19 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 18 33  1  0
M  END


  Mrv1572004221604402D          

 20 22  0  0  0  0            999 V2000
    4.9279    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
  9  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20  7  1  0  0  0  0
 20  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259987

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCOC1=CC=CC=C1C1=NC2=C(N=NN2)C(O)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C13H13N5O2/c1-2-7-20-9-6-4-3-5-8(9)11-14-12-10(13(19)15-11)16-18-17-12/h3-6H,2,7H2,1H3,(H2,14,15,16,17,18,19)

> <INCHI_KEY>
REZGGXNDEMKIQB-UHFFFAOYSA-N

> <FORMULA>
C13H13N5O2

> <MOLECULAR_WEIGHT>
271.28

> <EXACT_MASS>
271.106924679

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.127372612948818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2-propoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
3.031987752666666

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.87838141771315

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.003427510478093

> <JCHEM_PKA_STRONGEST_BASIC>
-0.16503521300023116

> <JCHEM_POLAR_SURFACE_AREA>
96.81

> <JCHEM_REFRACTIVITY>
84.11630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zaprinast

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259987
     RDKit          3D
zaprinast
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.9479   -2.2768    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -1.1701    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403   -1.2701   -0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -0.3609   -0.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8403    0.9677   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360    1.7922   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766    3.1679   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5131    3.7244   -0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    2.9096   -0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4114    1.5469   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    0.6988   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394    1.2239   -0.4101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9698    0.5054   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2402    1.0905   -0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038   -0.8558   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -1.8633   -0.0959 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787   -2.9802    0.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -2.7254   -0.0166 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -1.4000   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4679   -0.6196   -0.2308 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6232   -2.0927    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107   -2.2318    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363   -3.2523    0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597   -1.3671    1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -0.2477    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -2.3387   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734   -1.1531   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    1.4373   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    3.7927   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174    4.8049   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736    3.3604   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0248    0.6386   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9359   -3.4558    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 11  1  0
 19 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       9.199   2.547   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865   1.777   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.865   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -1.173  -1.303   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.531  -0.533   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    7                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    2   20                                                       
CONECT    8    5    9   11                                                  
CONECT    9    6    8   20                                                  
CONECT   10   12   13   16                                                  
CONECT   11    8   14   15                                                  
CONECT   12   10   14   17                                                  
CONECT   13   10   15   19                                                  
CONECT   14   11   12                                                       
CONECT   15   11   13                                                       
CONECT   16   10   18                                                       
CONECT   17   12   18                                                       
CONECT   18   16   17                                                       
CONECT   19   13                                                            
CONECT   20    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0259987
HETATM    1  C1  UNL     1       3.948  -2.277   0.901  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.884  -1.170   0.971  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.940  -1.270  -0.173  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.928  -0.361  -0.266  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.840   0.968  -0.397  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.936   1.792  -0.483  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.777   3.168  -0.620  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.513   3.724  -0.671  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.596   2.910  -0.586  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.411   1.547  -0.451  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.608   0.699  -0.362  1.00  0.00           C  
HETATM   12  N1  UNL     1      -2.839   1.224  -0.410  1.00  0.00           N  
HETATM   13  C11 UNL     1      -3.970   0.505  -0.335  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.240   1.091  -0.389  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.804  -0.856  -0.199  1.00  0.00           C  
HETATM   16  N2  UNL     1      -4.680  -1.863  -0.096  1.00  0.00           N  
HETATM   17  N3  UNL     1      -3.979  -2.980   0.013  1.00  0.00           N  
HETATM   18  N4  UNL     1      -2.681  -2.725  -0.017  1.00  0.00           N  
HETATM   19  C13 UNL     1      -2.546  -1.400  -0.149  1.00  0.00           C  
HETATM   20  N5  UNL     1      -1.468  -0.620  -0.231  1.00  0.00           N  
HETATM   21  H1  UNL     1       4.623  -2.093   0.057  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.511  -2.232   1.845  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.436  -3.252   0.850  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.360  -1.367   1.955  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.427  -0.248   1.110  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.621  -2.339  -0.235  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.573  -1.153  -1.107  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.957   1.437  -0.457  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.667   3.793  -0.685  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.417   4.805  -0.778  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.574   3.360  -0.628  1.00  0.00           H  
HETATM   32  H12 UNL     1      -6.025   0.639  -0.845  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.936  -3.456   0.054  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11
CONECT   11   12   12   20
CONECT   12   13
CONECT   13   14   15   15
CONECT   14   32
CONECT   15   16   19
CONECT   16   17   17
CONECT   17   18
CONECT   18   19   33
CONECT   19   20   20
END

HMDB0259987
     RDKit          3D
zaprinast
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.9479   -2.2768    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -1.1701    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403   -1.2701   -0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -0.3609   -0.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8403    0.9677   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360    1.7922   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766    3.1679   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5131    3.7244   -0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    2.9096   -0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4114    1.5469   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    0.6988   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394    1.2239   -0.4101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9698    0.5054   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2402    1.0905   -0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038   -0.8558   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -1.8633   -0.0959 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787   -2.9802    0.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -2.7254   -0.0166 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -1.4000   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4679   -0.6196   -0.2308 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6232   -2.0927    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107   -2.2318    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363   -3.2523    0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597   -1.3671    1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -0.2477    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -2.3387   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734   -1.1531   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570    1.4373   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    3.7927   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174    4.8049   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736    3.3604   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0248    0.6386   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9359   -3.4558    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 11  1  0
 19 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 14 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(2-Propoxyphenyl)-8-azapurin-6-one	MeSH
m And b 22,948	MeSH
Zaprinast	MeSH
m And b 22948	MeSH

Chemical Formula

C₁₃H₁₃N₅O₂

Average Molecular Weight

271.28

Monoisotopic Molecular Weight

271.106924679

IUPAC Name

5-(2-propoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol

Traditional Name

zaprinast

CAS Registry Number

Not Available

SMILES

CCCOC1=CC=CC=C1C1=NC2=C(N=NN2)C(O)=N1

InChI Identifier

InChI=1S/C13H13N5O2/c1-2-7-20-9-6-4-3-5-8(9)11-14-12-10(13(19)15-11)16-18-17-12/h3-6H,2,7H2,1H3,(H2,14,15,16,17,18,19)

InChI Key

REZGGXNDEMKIQB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triazolopyrimidines. These are polycyclic aromatic compounds containing triazole ring fused to a pyrimidine ring. Triazole is a five-membered ring consisting of two carbon atoms and three nitrogen atoms. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazolopyrimidines

Sub Class

Not Available

Direct Parent

Triazolopyrimidines

Alternative Parents

Substituents

Triazolopyrimidine
Phenoxy compound
Phenol ether
Alkyl aryl ether
Hydroxypyrimidine
Monocyclic benzene moiety
Benzenoid
Pyrimidine
Azole
Heteroaromatic compound
1,2,3-triazole
Triazole
Ether
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	2.06	ALOGPS
logP	3.03	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6	ChemAxon
pKa (Strongest Basic)	-0.17	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.81 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.12 m³·mol⁻¹	ChemAxon
Polarizability	27.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
AllCCS	[M+H]+	162.636	32859911
AllCCS	[M+H-H2O]+	159.005	32859911
AllCCS	[M+Na]+	166.975	32859911
AllCCS	[M+NH4]+	166.006	32859911
AllCCS	[M-H]-	164.424	32859911
AllCCS	[M+Na-2H]-	163.915	32859911
AllCCS	[M+HCOO]-	163.47	32859911
DeepCCS	[M+H]+	167.919	30932474
DeepCCS	[M-H]-	165.561	30932474
DeepCCS	[M-2H]-	198.447	30932474
DeepCCS	[M+Na]+	174.013	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.53 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2278 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1756.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	286.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	133.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	401.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	552.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	909.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	424.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1038.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	271.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	360.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	198.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	22.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
zaprinast	CCCOC1=CC=CC=C1C1=NC2=C(N=NN2)C(O)=N1	3017.2	Standard polar	33892256
zaprinast	CCCOC1=CC=CC=C1C1=NC2=C(N=NN2)C(O)=N1	2661.5	Standard non polar	33892256
zaprinast	CCCOC1=CC=CC=C1C1=NC2=C(N=NN2)C(O)=N1	2729.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
zaprinast,2TMS,isomer #1	CCCOC1=CC=CC=C1C1=NC(O[Si](C)(C)C)=C2N=NN([Si](C)(C)C)C2=N1	2708.2	Semi standard non polar	33892256
zaprinast,2TMS,isomer #1	CCCOC1=CC=CC=C1C1=NC(O[Si](C)(C)C)=C2N=NN([Si](C)(C)C)C2=N1	2639.1	Standard non polar	33892256
zaprinast,2TMS,isomer #1	CCCOC1=CC=CC=C1C1=NC(O[Si](C)(C)C)=C2N=NN([Si](C)(C)C)C2=N1	3340.7	Standard polar	33892256
zaprinast,2TBDMS,isomer #1	CCCOC1=CC=CC=C1C1=NC(O[Si](C)(C)C(C)(C)C)=C2N=NN([Si](C)(C)C(C)(C)C)C2=N1	3024.8	Semi standard non polar	33892256
zaprinast,2TBDMS,isomer #1	CCCOC1=CC=CC=C1C1=NC(O[Si](C)(C)C(C)(C)C)=C2N=NN([Si](C)(C)C(C)(C)C)C2=N1	3038.6	Standard non polar	33892256
zaprinast,2TBDMS,isomer #1	CCCOC1=CC=CC=C1C1=NC(O[Si](C)(C)C(C)(C)C)=C2N=NN([Si](C)(C)C(C)(C)C)C2=N1	3424.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zaprinast GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-2390000000-6130fda29121bfe0a402	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zaprinast GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zaprinast GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zaprinast GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zaprinast GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zaprinast GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	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 - Zaprinast 10V, Positive-QTOF	splash10-00di-1090000000-224b9856da060d4c3dd7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaprinast 20V, Positive-QTOF	splash10-006x-5090000000-3a7f38206b08e3d3da28	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaprinast 40V, Positive-QTOF	splash10-0006-9230000000-38c7a4e611fa82b36c67	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaprinast 10V, Negative-QTOF	splash10-00di-0090000000-453859f84d8f9c3b3f46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaprinast 20V, Negative-QTOF	splash10-00b9-0190000000-cfcafa23f98dc7383295	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zaprinast 40V, Negative-QTOF	splash10-002b-2950000000-0251af63f318e67f9dda	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5520

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Zaprinast (HMDB0259987)

MOL for HMDB0259987 (Zaprinast)

3D MOL for HMDB0259987 (Zaprinast)

3D SDF for HMDB0259987 (Zaprinast)

3D-SDF for HMDB0259987 (Zaprinast)

PDB for HMDB0259987 (Zaprinast)

3D PDB for HMDB0259987 (Zaprinast)

SMILES for HMDB0259987 (Zaprinast)

INCHI for HMDB0259987 (Zaprinast)

Structure for HMDB0259987 (Zaprinast)

3D Structure for HMDB0259987 (Zaprinast)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra