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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:26:07 UTC

Update Date

2021-09-26 22:57:07 UTC

HMDB ID

HMDB0247428

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Chloroinosine

Description

8-Chloroinosine belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Based on a literature review a small amount of articles have been published on 8-Chloroinosine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-chloroinosine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Chloroinosine 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

HMDB0247428
     RDKit          3D
8-Chloroinosine
 31 33  0  0  0  0  0  0  0  0999 V2000
    4.9819    1.4898   -0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1207    0.7405   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3336    0.0033    0.8284 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678   -0.7887    1.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -0.8852    0.8063 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998   -0.1602   -0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746    0.6614   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2848    1.2173   -1.9286 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203    0.7665   -2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684    1.2691   -3.3004 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7758   -0.0891   -1.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -0.7575   -0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862    0.1309   -1.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621    0.6056   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858    1.2460   -0.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    2.3080   -1.1559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895   -0.6945    0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0032   -1.6008    0.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350   -1.1574    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -2.5078    0.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603    0.0383    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022   -1.3666    2.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697   -1.6839   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561    1.2314    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1566    0.5758   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    1.6669    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3617    3.1876   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430   -0.5200    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993   -1.3302   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1530   -0.5665    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918   -3.0299    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7  2  1  0
 19 12  1  0
 11  6  1  0
  3 21  1  0
  4 22  1  0
 12 23  1  0
 14 24  1  0
 15 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END


  Mrv1652309112102262D          

 20 22  0  0  0  0            999 V2000
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 N   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
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -0.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 12 19  1  0  0  0  0
  9 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247428

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(C(O)C1O)N1C(Cl)=NC2=C1N=CNC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H11ClN4O5/c11-10-14-4-7(12-2-13-8(4)19)15(10)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H,12,13,19)

> <INCHI_KEY>
ROPMUQKCJYNROP-UHFFFAOYSA-N

> <FORMULA>
C10H11ClN4O5

> <MOLECULAR_WEIGHT>
302.67

> <EXACT_MASS>
302.0417972

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.89578243935827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

> <ALOGPS_LOGP>
-1.01

> <JCHEM_LOGP>
-1.564523708666667

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.453330424493853

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.894901278151092

> <JCHEM_PKA_STRONGEST_BASIC>
-1.957879974011281

> <JCHEM_POLAR_SURFACE_AREA>
129.20000000000002

> <JCHEM_REFRACTIVITY>
66.35770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247428
     RDKit          3D
8-Chloroinosine
 31 33  0  0  0  0  0  0  0  0999 V2000
    4.9819    1.4898   -0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1207    0.7405   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3336    0.0033    0.8284 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678   -0.7887    1.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -0.8852    0.8063 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998   -0.1602   -0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746    0.6614   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2848    1.2173   -1.9286 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203    0.7665   -2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684    1.2691   -3.3004 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7758   -0.0891   -1.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -0.7575   -0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862    0.1309   -1.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621    0.6056   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858    1.2460   -0.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    2.3080   -1.1559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895   -0.6945    0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0032   -1.6008    0.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350   -1.1574    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -2.5078    0.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603    0.0383    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022   -1.3666    2.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697   -1.6839   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561    1.2314    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1566    0.5758   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    1.6669    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3617    3.1876   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430   -0.5200    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993   -1.3302   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1530   -0.5665    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918   -3.0299    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7  2  1  0
 19 12  1  0
 11  6  1  0
  3 21  1  0
  4 22  1  0
 12 23  1  0
 14 24  1  0
 15 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.530   1.303   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       3.864   3.613   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.161  -1.114   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.744  -2.359   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.208  -1.884   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.208  -0.344   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.454  -2.789   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.293  -4.320   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.268  -3.824   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.701  -1.114   0.000  0.00  0.00           O+0
HETATM   20 Cl   UNK     0      -2.713   2.843   0.000  0.00  0.00          Cl+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   11                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   12                                                            
CONECT   20    9                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0247428
HETATM    1  O1  UNL     1       4.982   1.490  -0.800  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.121   0.741  -0.275  1.00  0.00           C  
HETATM    3  N1  UNL     1       4.334   0.003   0.828  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.368  -0.789   1.352  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.148  -0.885   0.806  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.900  -0.160  -0.300  1.00  0.00           C  
HETATM    7  C4  UNL     1       2.875   0.661  -0.859  1.00  0.00           C  
HETATM    8  N3  UNL     1       2.285   1.217  -1.929  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.020   0.767  -2.026  1.00  0.00           C  
HETATM   10 CL1  UNL     1      -0.068   1.269  -3.300  1.00  0.00          CL  
HETATM   11  N4  UNL     1       0.776  -0.089  -1.017  1.00  0.00           N  
HETATM   12  C6  UNL     1      -0.483  -0.758  -0.821  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.486   0.131  -1.181  1.00  0.00           O  
HETATM   14  C7  UNL     1      -2.062   0.606  -0.018  1.00  0.00           C  
HETATM   15  C8  UNL     1      -3.386   1.246  -0.278  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.178   2.308  -1.156  1.00  0.00           O  
HETATM   17  C9  UNL     1      -2.189  -0.694   0.782  1.00  0.00           C  
HETATM   18  O4  UNL     1      -3.003  -1.601   0.126  1.00  0.00           O  
HETATM   19  C10 UNL     1      -0.735  -1.157   0.604  1.00  0.00           C  
HETATM   20  O5  UNL     1      -0.600  -2.508   0.835  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.260   0.038   1.294  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.602  -1.367   2.255  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.570  -1.684  -1.441  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.356   1.231   0.525  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.157   0.576  -0.642  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.748   1.667   0.693  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.362   3.188  -0.707  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.443  -0.520   1.826  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.199  -1.330  -0.806  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.153  -0.566   1.331  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.492  -3.030   0.008  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6
CONECT    6    7    7   11
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   11
CONECT   11   12
CONECT   12   13   19   23
CONECT   13   14
CONECT   14   15   17   24
CONECT   15   16   25   26
CONECT   16   27
CONECT   17   18   19   28
CONECT   18   29
CONECT   19   20   30
CONECT   20   31
END

HMDB0247428
     RDKit          3D
8-Chloroinosine
 31 33  0  0  0  0  0  0  0  0999 V2000
    4.9819    1.4898   -0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1207    0.7405   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3336    0.0033    0.8284 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678   -0.7887    1.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -0.8852    0.8063 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998   -0.1602   -0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746    0.6614   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2848    1.2173   -1.9286 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203    0.7665   -2.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0684    1.2691   -3.3004 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7758   -0.0891   -1.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -0.7575   -0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862    0.1309   -1.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621    0.6056   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3858    1.2460   -0.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    2.3080   -1.1559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895   -0.6945    0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0032   -1.6008    0.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350   -1.1574    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -2.5078    0.8352 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603    0.0383    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022   -1.3666    2.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697   -1.6839   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561    1.2314    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1566    0.5758   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    1.6669    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3617    3.1876   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430   -0.5200    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993   -1.3302   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1530   -0.5665    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918   -3.0299    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7  2  1  0
 19 12  1  0
 11  6  1  0
  3 21  1  0
  4 22  1  0
 12 23  1  0
 14 24  1  0
 15 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₁ClN₄O₅

Average Molecular Weight

302.67

Monoisotopic Molecular Weight

302.0417972

IUPAC Name

8-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

Traditional Name

8-chloro-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one

CAS Registry Number

Not Available

SMILES

OCC1OC(C(O)C1O)N1C(Cl)=NC2=C1N=CNC2=O

InChI Identifier

InChI=1S/C10H11ClN4O5/c11-10-14-4-7(12-2-13-8(4)19)15(10)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H,12,13,19)

InChI Key

ROPMUQKCJYNROP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Pentose monosaccharide
Purinone
Imidazopyrimidine
Purine
Pyrimidone
Aryl chloride
Aryl halide
Monosaccharide
N-substituted imidazole
Pyrimidine
Azole
Heteroaromatic compound
Imidazole
Vinylogous amide
Oxolane
Lactam
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organochloride
Organohalogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Primary alcohol
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	-1	ALOGPS
logP	-1.6	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.36 m³·mol⁻¹	ChemAxon
Polarizability	26.9 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	155.984	30932474
DeepCCS	[M-H]-	153.626	30932474
DeepCCS	[M-2H]-	186.511	30932474
DeepCCS	[M+Na]+	162.077	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.3682 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1178.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	266.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	323.7 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	308.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	134.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	659.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	257.2 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	1015.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	485.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	208.0 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	152.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Chloroinosine	OCC1OC(C(O)C1O)N1C(Cl)=NC2=C1N=CNC2=O	3627.5	Standard polar	33892256
8-Chloroinosine	OCC1OC(C(O)C1O)N1C(Cl)=NC2=C1N=CNC2=O	1908.5	Standard non polar	33892256
8-Chloroinosine	OCC1OC(C(O)C1O)N1C(Cl)=NC2=C1N=CNC2=O	2892.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Chloroinosine,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C(Cl)=NC3=C2N=CN([Si](C)(C)C)C3=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2701.5	Semi standard non polar	33892256
8-Chloroinosine,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C(Cl)=NC3=C2N=CN([Si](C)(C)C)C3=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2808.5	Standard non polar	33892256
8-Chloroinosine,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C(Cl)=NC3=C2N=CN([Si](C)(C)C)C3=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3145.4	Standard polar	33892256
8-Chloroinosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C(Cl)=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3516.5	Semi standard non polar	33892256
8-Chloroinosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C(Cl)=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3546.0	Standard non polar	33892256
8-Chloroinosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C(Cl)=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3453.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05iu-9140000000-69e1b6a6d48a8d8749ed	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloroinosine GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-03	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 - 8-Chloroinosine 10V, Positive-QTOF	splash10-0udi-0019000000-83548e86fb8199358921	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloroinosine 20V, Positive-QTOF	splash10-0fk9-0945000000-d64c53797b7dd3ff7287	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloroinosine 40V, Positive-QTOF	splash10-0229-2910000000-0d53d1984436c19be65a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloroinosine 10V, Negative-QTOF	splash10-0ue9-0079000000-843578db16279d26ed85	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloroinosine 20V, Negative-QTOF	splash10-0159-2952000000-84091ea152e66eb8e52f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloroinosine 40V, Negative-QTOF	splash10-001i-6900000000-3c738957d35b15db2431	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

11318076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16759255

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 8-Chloroinosine (HMDB0247428)

MOL for HMDB0247428 (8-Chloroinosine)

3D MOL for HMDB0247428 (8-Chloroinosine)

3D SDF for HMDB0247428 (8-Chloroinosine)

3D-SDF for HMDB0247428 (8-Chloroinosine)

PDB for HMDB0247428 (8-Chloroinosine)

3D PDB for HMDB0247428 (8-Chloroinosine)

SMILES for HMDB0247428 (8-Chloroinosine)

INCHI for HMDB0247428 (8-Chloroinosine)

Structure for HMDB0247428 (8-Chloroinosine)

3D Structure for HMDB0247428 (8-Chloroinosine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra