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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 15:43:39 UTC

Update Date

2021-09-14 15:40:09 UTC

HMDB ID

HMDB0006555

Secondary Accession Numbers

HMDB06555

Metabolite Identification

Common Name

dIMP

Description

dIMP is a deoxyribonucleoside and is considered a derivative of the nucleoside inosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2' position of its ribose sugar moiety. The hydrolytic deamination of dAMP residues in DNA yields dIMP residues. The deamination of adenine residues in DNA generates hypoxanthine, which is mutagenic since it can pair not only with thymine but also with cytosine and therefore would result in A-T to G-C transitions after DNA replication. Hypoxanthine DNA glycosylase (EC 3.2.2.15) excises hypoxanthine from DNA containing dIMP residues in mammalian cells. (PMID: 10684927 , 8016081 ).

Structure

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

HMDB0006555
     RDKit          3D
dIMP
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.7774    4.0383   -0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7222    2.7815   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8592    2.0804   -0.4685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8119    0.7227   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6617    0.0784   -0.2057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151    0.7443    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514    2.1156    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3189    2.5866    0.2683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297    1.5184    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2603    0.3952    0.2943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283   -0.9246    0.4137 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4196   -1.5699   -0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6337   -2.5851   -0.4567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0401   -3.5655    0.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3600   -1.7185    0.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4067   -0.8487   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -0.0812    0.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    0.9464    0.3242 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3674    0.0801   -0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6576    1.9479    1.6136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6643    1.8953   -0.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074   -0.9556    1.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7153    0.1575   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384   -0.9512   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5223    1.5723    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -1.5886    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -0.8086   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2751   -2.0604   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551   -2.9443   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0968   -3.3439    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8705   -2.3426    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9663   -0.1588   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -1.4778   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8474    2.8564    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0548    1.4081   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 15 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 11 26  1  1
 12 27  1  0
 12 28  1  0
 13 29  1  6
 14 30  1  0
 15 31  1  1
 16 32  1  0
 16 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv0541 02231220432D          

 22 24  0  0  1  0            999 V2000
   18.0791   -4.0947    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.5471   -6.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4856   -6.0494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3327   -4.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8642   -3.8411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8255   -3.3096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2794  -10.7099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2940   -4.3483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7746   -8.3960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2794   -8.2349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7746   -9.7238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5650   -9.4724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0308   -7.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8174   -6.5332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8159   -7.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0332   -6.2770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7796   -5.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9940   -8.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2561   -9.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9940   -9.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2794   -9.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5650   -8.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1  8  2  0  0  0  0
  2 13  1  0  0  0  0
  2 16  1  0  0  0  0
 14  3  1  1  0  0  0
  4 17  1  0  0  0  0
  7 21  2  0  0  0  0
 13  9  1  6  0  0  0
  9 18  1  0  0  0  0
  9 19  1  0  0  0  0
 10 18  1  0  0  0  0
 10 22  1  0  0  0  0
 11 19  2  0  0  0  0
 11 20  1  0  0  0  0
 12 21  1  0  0  0  0
 12 22  2  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006555

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N4O7P/c15-5-1-7(21-6(5)2-20-22(17,18)19)14-4-13-8-9(14)11-3-12-10(8)16/h3-7,15H,1-2H2,(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1

> <INCHI_KEY>
PHNGFPPXDJJADG-RRKCRQDMSA-N

> <FORMULA>
C10H13N4O7P

> <MOLECULAR_WEIGHT>
332.2066

> <EXACT_MASS>
332.052185302

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
27.21289510735804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.58

> <JCHEM_LOGP>
-2.6103145453338015

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
6.176487600014412

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2190853577630598

> <JCHEM_PKA_STRONGEST_BASIC>
2.766144770170425

> <JCHEM_POLAR_SURFACE_AREA>
155.5

> <JCHEM_REFRACTIVITY>
70.2606

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006555
     RDKit          3D
dIMP
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.7774    4.0383   -0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7222    2.7815   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8592    2.0804   -0.4685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8119    0.7227   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6617    0.0784   -0.2057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151    0.7443    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514    2.1156    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3189    2.5866    0.2683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297    1.5184    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2603    0.3952    0.2943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283   -0.9246    0.4137 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4196   -1.5699   -0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6337   -2.5851   -0.4567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0401   -3.5655    0.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3600   -1.7185    0.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4067   -0.8487   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -0.0812    0.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    0.9464    0.3242 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3674    0.0801   -0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6576    1.9479    1.6136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6643    1.8953   -0.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074   -0.9556    1.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7153    0.1575   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384   -0.9512   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5223    1.5723    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -1.5886    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -0.8086   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2751   -2.0604   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551   -2.9443   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0968   -3.3439    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8705   -2.3426    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9663   -0.1588   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -1.4778   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8474    2.8564    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0548    1.4081   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 15 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 11 26  1  1
 12 27  1  0
 12 28  1  0
 13 29  1  6
 14 30  1  0
 15 31  1  1
 16 32  1  0
 16 33  1  0
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0      33.748  -7.643   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      32.755 -12.961   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      36.373 -11.292   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      34.221  -9.109   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      35.213  -7.170   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      33.274  -6.178   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      30.388 -19.992   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      32.282  -8.117   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      33.179 -15.673   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      30.388 -15.372   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      33.179 -18.151   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      29.055 -17.682   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      33.657 -14.209   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.126 -12.195   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.123 -13.735   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.662 -11.717   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.189 -10.252   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.722 -16.142   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.078 -16.912   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.722 -17.682   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.388 -18.452   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.055 -16.142   0.000  0.00  0.00           C+0
CONECT    1    4    5    6    8                                             
CONECT    2   13   16                                                       
CONECT    3   14                                                            
CONECT    4    1   17                                                       
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7   21                                                            
CONECT    8    1                                                            
CONECT    9   13   18   19                                                  
CONECT   10   18   22                                                       
CONECT   11   19   20                                                       
CONECT   12   21   22                                                       
CONECT   13    2    9   15                                                  
CONECT   14    3   15   16                                                  
CONECT   15   13   14                                                       
CONECT   16    2   14   17                                                  
CONECT   17    4   16                                                       
CONECT   18    9   10   20                                                  
CONECT   19    9   11                                                       
CONECT   20   11   18   21                                                  
CONECT   21    7   12   20                                                  
CONECT   22   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0006555
HETATM    1  O1  UNL     1      -3.777   4.038  -0.255  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.722   2.781  -0.235  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.859   2.080  -0.469  1.00  0.00           N  
HETATM    4  C2  UNL     1      -4.812   0.723  -0.450  1.00  0.00           C  
HETATM    5  N2  UNL     1      -3.662   0.078  -0.206  1.00  0.00           N  
HETATM    6  C3  UNL     1      -2.515   0.744   0.030  1.00  0.00           C  
HETATM    7  C4  UNL     1      -2.551   2.116   0.014  1.00  0.00           C  
HETATM    8  N3  UNL     1      -1.319   2.587   0.268  1.00  0.00           N  
HETATM    9  C5  UNL     1      -0.530   1.518   0.440  1.00  0.00           C  
HETATM   10  N4  UNL     1      -1.260   0.395   0.294  1.00  0.00           N  
HETATM   11  C6  UNL     1      -0.728  -0.925   0.414  1.00  0.00           C  
HETATM   12  C7  UNL     1      -0.420  -1.570  -0.925  1.00  0.00           C  
HETATM   13  C8  UNL     1       0.634  -2.585  -0.457  1.00  0.00           C  
HETATM   14  O2  UNL     1      -0.040  -3.566   0.249  1.00  0.00           O  
HETATM   15  C9  UNL     1       1.360  -1.718   0.548  1.00  0.00           C  
HETATM   16  C10 UNL     1       2.407  -0.849  -0.110  1.00  0.00           C  
HETATM   17  O3  UNL     1       2.994  -0.081   0.891  1.00  0.00           O  
HETATM   18  P1  UNL     1       4.186   0.946   0.324  1.00  0.00           P  
HETATM   19  O4  UNL     1       5.367   0.080  -0.112  1.00  0.00           O  
HETATM   20  O5  UNL     1       4.658   1.948   1.614  1.00  0.00           O  
HETATM   21  O6  UNL     1       3.664   1.895  -0.973  1.00  0.00           O  
HETATM   22  O7  UNL     1       0.407  -0.956   1.168  1.00  0.00           O  
HETATM   23  H1  UNL     1      -5.715   0.158  -0.635  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.638  -0.951  -0.194  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.522   1.572   0.660  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.485  -1.589   0.918  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.078  -0.809  -1.554  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.275  -2.060  -1.383  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.255  -2.944  -1.268  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.097  -3.344   1.233  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.870  -2.343   1.299  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.966  -0.159  -0.856  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.135  -1.478  -0.652  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.847   2.856   1.275  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.055   1.408  -1.582  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4    4
CONECT    4    5   23
CONECT    5    6   24
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   25
CONECT   10   11
CONECT   11   12   22   26
CONECT   12   13   27   28
CONECT   13   14   15   29
CONECT   14   30
CONECT   15   16   22   31
CONECT   16   17   32   33
CONECT   17   18
CONECT   18   19   19   20   21
CONECT   20   34
CONECT   21   35
END

HMDB0006555
     RDKit          3D
dIMP
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.7774    4.0383   -0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7222    2.7815   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8592    2.0804   -0.4685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8119    0.7227   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6617    0.0784   -0.2057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151    0.7443    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514    2.1156    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3189    2.5866    0.2683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297    1.5184    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2603    0.3952    0.2943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283   -0.9246    0.4137 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4196   -1.5699   -0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6337   -2.5851   -0.4567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0401   -3.5655    0.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3600   -1.7185    0.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4067   -0.8487   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -0.0812    0.8915 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    0.9464    0.3242 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3674    0.0801   -0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6576    1.9479    1.6136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6643    1.8953   -0.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4074   -0.9556    1.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7153    0.1575   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384   -0.9512   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5223    1.5723    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -1.5886    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0778   -0.8086   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2751   -2.0604   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551   -2.9443   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0968   -3.3439    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8705   -2.3426    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9663   -0.1588   -0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -1.4778   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8474    2.8564    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0548    1.4081   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 15 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 11 26  1  1
 12 27  1  0
 12 28  1  0
 13 29  1  6
 14 30  1  0
 15 31  1  1
 16 32  1  0
 16 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2'-Deoxy-5'-inosinic acid	ChEBI
2'-Deoxyinosine 5'-monophosphate	ChEBI
2'-Deoxyinosine 5'-monophosphoric acid	ChEBI
2'-Deoxyinosine 5'-phosphate	ChEBI
9-(2-Deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-9H-purin-6-ol	ChEBI
9-(2-Deoxy-5-O-phosphono-beta-delta-erythro-pentofuranosyl)-9H-purin-6-ol	ChEBI
Deoxyinosine monophosphate	ChEBI
2'-Deoxy-5'-inosinate	Generator
2'-Deoxyinosine 5'-phosphoric acid	Generator
9-(2-Deoxy-5-O-phosphono-b-D-erythro-pentofuranosyl)-9H-purin-6-ol	Generator
9-(2-Deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-ol	Generator
9-(2-Deoxy-5-O-phosphono-b-delta-erythro-pentofuranosyl)-9H-purin-6-ol	Generator
9-(2-Deoxy-5-O-phosphono-β-δ-erythro-pentofuranosyl)-9H-purin-6-ol	Generator
Deoxyinosine monophosphoric acid	Generator
9-(2-Deoxy-5-O-phosphono-b-δ-erythro-pentofuranosyl)-9H-purin-6-ol	HMDB
Hypoxanthine deoxyriboside	HMDB
[(2R,3S,4R,5R)-3-Hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate	HMDB
Deoxy imp	HMDB
2'-Deoxyinosine-5'-monophosphoric acid	HMDB
DIMP	ChEBI

Chemical Formula

C₁₀H₁₃N₄O₇P

Average Molecular Weight

332.2066

Monoisotopic Molecular Weight

332.052185302

IUPAC Name

{[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

3393-18-8

SMILES

O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O

InChI Identifier

InChI=1S/C10H13N4O7P/c15-5-1-7(21-6(5)2-20-22(17,18)19)14-4-13-8-9(14)11-3-12-10(8)16/h3-7,15H,1-2H2,(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1

InChI Key

PHNGFPPXDJJADG-RRKCRQDMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine deoxyribonucleotides

Direct Parent

Purine 2'-deoxyribonucleoside monophosphates

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside monophosphate
Hypoxanthine
Imidazopyrimidine
Purine
Hydroxypyrimidine
Monoalkyl phosphate
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:28806 )
deoxyinosine phosphate (CHEBI:28806 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006555)

Source

Endogenous

Endogenous (HMDB: HMDB0006555)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

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	2.1 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	2.77	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	155.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.26 m³·mol⁻¹	ChemAxon
Polarizability	27.21 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
DarkChem	[M+H]+	172.165	31661259
DarkChem	[M-H]-	167.978	31661259
DeepCCS	[M+H]+	154.395	30932474
DeepCCS	[M-H]-	152.0	30932474
DeepCCS	[M-2H]-	186.484	30932474
DeepCCS	[M+Na]+	161.17	30932474
AllCCS	[M+H]+	171.5	32859911
AllCCS	[M+H-H2O]+	168.5	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.1	32859911
AllCCS	[M-H]-	167.4	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	166.7	32859911

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.	2.98 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3803 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.48 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	320.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	671.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	238.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	58.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	310.0 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	274.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	720.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	584.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	116.6 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	678.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	204.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	720.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	264.6 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	389.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
dIMP	O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O	3877.4	Standard polar	33892256
dIMP	O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O	2118.0	Standard non polar	33892256
dIMP	O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O	3397.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
dIMP,1TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)O	2762.4	Semi standard non polar	33892256
dIMP,1TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O	2880.0	Semi standard non polar	33892256
dIMP,1TMS,isomer #3	C[Si](C)(C)N1C=NC(=O)C2=C1N([C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)C=N2	2870.8	Semi standard non polar	33892256
dIMP,2TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	2815.6	Semi standard non polar	33892256
dIMP,2TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	3175.2	Standard non polar	33892256
dIMP,2TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	4375.8	Standard polar	33892256
dIMP,2TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O	2843.1	Semi standard non polar	33892256
dIMP,2TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O	3247.4	Standard non polar	33892256
dIMP,2TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O	4814.0	Standard polar	33892256
dIMP,2TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O)O[Si](C)(C)C	2848.0	Semi standard non polar	33892256
dIMP,2TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O)O[Si](C)(C)C	3159.7	Standard non polar	33892256
dIMP,2TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O)O[Si](C)(C)C	4076.7	Standard polar	33892256
dIMP,2TMS,isomer #4	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)C[C@@H]1O	2960.6	Semi standard non polar	33892256
dIMP,2TMS,isomer #4	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)C[C@@H]1O	3211.7	Standard non polar	33892256
dIMP,2TMS,isomer #4	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)C[C@@H]1O	4378.4	Standard polar	33892256
dIMP,3TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2827.2	Semi standard non polar	33892256
dIMP,3TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3169.5	Standard non polar	33892256
dIMP,3TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3813.7	Standard polar	33892256
dIMP,3TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	2944.2	Semi standard non polar	33892256
dIMP,3TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	3210.8	Standard non polar	33892256
dIMP,3TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	4103.5	Standard polar	33892256
dIMP,3TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)C[C@@H]1O)O[Si](C)(C)C	2976.5	Semi standard non polar	33892256
dIMP,3TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)C[C@@H]1O)O[Si](C)(C)C	3217.8	Standard non polar	33892256
dIMP,3TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)C[C@@H]1O)O[Si](C)(C)C	3842.0	Standard polar	33892256
dIMP,4TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2977.7	Semi standard non polar	33892256
dIMP,4TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3189.6	Standard non polar	33892256
dIMP,4TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3629.8	Standard polar	33892256
dIMP,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)O	3013.6	Semi standard non polar	33892256
dIMP,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O	3106.1	Semi standard non polar	33892256
dIMP,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC(=O)C2=C1N([C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)C=N2	3117.6	Semi standard non polar	33892256
dIMP,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	3261.7	Semi standard non polar	33892256
dIMP,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	3593.3	Standard non polar	33892256
dIMP,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	4422.5	Standard polar	33892256
dIMP,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O	3316.5	Semi standard non polar	33892256
dIMP,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O	3676.3	Standard non polar	33892256
dIMP,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O	4709.8	Standard polar	33892256
dIMP,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3267.9	Semi standard non polar	33892256
dIMP,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3552.7	Standard non polar	33892256
dIMP,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2[NH]C=NC3=O)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	4215.9	Standard polar	33892256
dIMP,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)C[C@@H]1O	3384.0	Semi standard non polar	33892256
dIMP,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)C[C@@H]1O	3606.0	Standard non polar	33892256
dIMP,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)C[C@@H]1O	4407.5	Standard polar	33892256
dIMP,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3443.2	Semi standard non polar	33892256
dIMP,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3751.7	Standard non polar	33892256
dIMP,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2[NH]C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4010.3	Standard polar	33892256
dIMP,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	3548.2	Semi standard non polar	33892256
dIMP,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	3807.8	Standard non polar	33892256
dIMP,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	4175.6	Standard polar	33892256
dIMP,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3557.4	Semi standard non polar	33892256
dIMP,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3778.7	Standard non polar	33892256
dIMP,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	4010.7	Standard polar	33892256
dIMP,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3716.0	Semi standard non polar	33892256
dIMP,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3917.6	Standard non polar	33892256
dIMP,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3863.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - dIMP GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-001i-9210000000-53948c1a90a0f6914597	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - dIMP GC-EI-TOF (Non-derivatized)	splash10-001i-9210000000-53948c1a90a0f6914597	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - dIMP GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9401000000-3e05abb6a8d8b1a335b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - dIMP GC-MS (1 TMS) - 70eV, Positive	splash10-00rx-7923000000-8831273c387905273e72	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - dIMP 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - dIMP LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-001r-0619000000-1a0eb2cb24a05602189f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - dIMP LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOF	splash10-000i-2902000000-8031212ff8d5a3caf932	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - dIMP LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-005j-9803000000-e0eccae074a61767e080	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - dIMP LC-ESI-QTOF , negative-QTOF	splash10-005j-9803000000-e0eccae074a61767e080	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - dIMP LC-ESI-QTOF , positive-QTOF	splash10-001r-0619000000-1a0eb2cb24a05602189f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - dIMP LC-ESI-QTOF , positive-QTOF	splash10-000i-2902000000-8031212ff8d5a3caf932	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - dIMP 30V, Positive-QTOF	splash10-000i-2902000000-8031212ff8d5a3caf932	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 10V, Positive-QTOF	splash10-000i-0901000000-82485bc6f5afd265ffb6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 20V, Positive-QTOF	splash10-000i-0900000000-40c3e510e6f14b9c6415	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 40V, Positive-QTOF	splash10-000i-0900000000-084491e4ef779439c6e7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 10V, Negative-QTOF	splash10-003r-5209000000-fe97448e2adad18be4e1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 20V, Negative-QTOF	splash10-004r-9400000000-69f08fb1d6025455e334	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 40V, Negative-QTOF	splash10-004i-9000000000-eaad95f8c8f37f17a06d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 10V, Positive-QTOF	splash10-000i-0900000000-b2e36fb98660834d7d24	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 20V, Positive-QTOF	splash10-000i-0900000000-c7e643ad3fc1ffc399bb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 40V, Positive-QTOF	splash10-0019-5900000000-13459080c7272714095d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 10V, Negative-QTOF	splash10-003r-9008000000-2805c5fa43654779dc36	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 20V, Negative-QTOF	splash10-004i-9101000000-bc2b5d6253fd7cf52a89	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - dIMP 40V, Negative-QTOF	splash10-004i-9000000000-ee07b6d42071fb27d3f4	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB023969

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Deoxyinosine_monophosphate

METLIN ID

Not Available

PubChem Compound

91531

PDB ID

Not Available

ChEBI ID

28806

Food Biomarker Ontology

Not Available

VMH ID

DIMP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ogilvie, Kelvin K.; Slotin, Lewis A. Anhydronucleosides. XI. Synthesis of nucleotides from 8,2'-thioanhydropurine nucleosides. Canadian Journal of Chemistry (1973), 51(14), 2397-405.

Material Safety Data Sheet (MSDS)

Not Available

General References

Saparbaev M, Mani JC, Laval J: Interactions of the human, rat, Saccharomyces cerevisiae and Escherichia coli 3-methyladenine-DNA glycosylases with DNA containing dIMP residues. Nucleic Acids Res. 2000 Mar 15;28(6):1332-9. [PubMed:10684927 ]
Saparbaev M, Laval J: Excision of hypoxanthine from DNA containing dIMP residues by the Escherichia coli, yeast, rat, and human alkylpurine DNA glycosylases. Proc Natl Acad Sci U S A. 1994 Jun 21;91(13):5873-7. [PubMed:8016081 ]

Enzymes

Enzyme Details

1. 5'(3')-deoxyribonucleotidase, mitochondrial

General function:: Involved in phosphatase activity
Specific function:: Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:: NT5M
Uniprot ID:: Q9NPB1
Molecular weight:: Not Available

Enzyme Details

2. Inosine triphosphate pyrophosphatase

General function:: Involved in hydrolase activity
Specific function:: Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:: ITPA
Uniprot ID:: Q9BY32
Molecular weight:: 16833.23

Reactions

2'-Deoxyinosine triphosphate + Water → dIMP + Pyrophosphate	details

Showing metabocard for dIMP (HMDB0006555)

MOL for HMDB0006555 (dIMP)

3D MOL for HMDB0006555 (dIMP)

3D SDF for HMDB0006555 (dIMP)

3D-SDF for HMDB0006555 (dIMP)

PDB for HMDB0006555 (dIMP)

3D PDB for HMDB0006555 (dIMP)

SMILES for HMDB0006555 (dIMP)

INCHI for HMDB0006555 (dIMP)

Structure for HMDB0006555 (dIMP)

3D Structure for HMDB0006555 (dIMP)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions