MiMeDB: Showing metabocard for DIMP (MMDBc0029837)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:43:42 UTC

Update Date

2022-08-31 17:19:13 UTC

Metabolite ID

MMDBc0029837

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 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>
MMDBc0029837

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₀H₁₃N₄O₇P

Average Mass

332.2066

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-001i-9210000000-53948c1a90a0f6914597	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-9210000000-53948c1a90a0f6914597	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9401000000-3e05abb6a8d8b1a335b6	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00rx-7923000000-8831273c387905273e72	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001r-0619000000-1a0eb2cb24a05602189f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-000i-2902000000-8031212ff8d5a3caf932	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-005j-9803000000-e0eccae074a61767e080	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-005j-9803000000-e0eccae074a61767e080	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001r-0619000000-1a0eb2cb24a05602189f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-2902000000-8031212ff8d5a3caf932	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-2902000000-8031212ff8d5a3caf932	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0901000000-82485bc6f5afd265ffb6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-40c3e510e6f14b9c6415	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-084491e4ef779439c6e7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-5209000000-fe97448e2adad18be4e1	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-9400000000-69f08fb1d6025455e334	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-eaad95f8c8f37f17a06d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-b2e36fb98660834d7d24	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-c7e643ad3fc1ffc399bb	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-5900000000-13459080c7272714095d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-9008000000-2805c5fa43654779dc36	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9101000000-bc2b5d6253fd7cf52a89	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-ee07b6d42071fb27d3f4	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo sapiens
MMDBp0192097	Inosine triphosphate pyrophosphatase	Unknown	Q9BY32	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001784	DIMP	Deoxyinosine	5', 3'-nucleotidase, cytosolic	5'-Nucleotidase (DIMP)	VMH	10899995
MMDBr0001801	2'-Deoxyinosine triphosphate	DIMP	Inosine triphosphatase (nucleoside triphosphate pyrophosphatase)	Nucleoside Triphosphate Pyrophosphorylase (dITP)	VMH	30371894
MMDBr0014816	2'-Deoxyinosine triphosphate	DIMP	Inosine triphosphate pyrophosphatase	Dephosphorylation	RHEA	34755880
MMDBr0014817	2'-Deoxyinosine triphosphate	DIMP	Inosine triphosphate pyrophosphatase	Dephosphorylation	RHEA	34755880
MMDBr0014907	DIMP	Deoxyinosine	5'-deoxynucleotidase YfbR	Hydrolysis of nucleotide	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	105	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Chicken ; Cattle	Unknown
Eukaryota/Fungi	Ascomycota	22
Eukaryota/Fungi	Chytridiomycota	1
Eukaryota/Fungi	Basidiomycota	4
Eukaryota/Fungi	Microsporidia	2
Bacteria	Tenericutes	3	Human
Bacteria	Acidobacteria	1
Bacteria	Firmicutes	50	Human feces; Human
Bacteria	Aquificae	3
Archaea/Archaea	Euryarchaeota	11
Bacteria	Bacteroidetes	7	Human ; Human feces
Bacteria	Actinobacteria	24	Human ; Human feces; Cattle
Bacteria	Spirochaetes	12	Human
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Chlorobi	1
Bacteria	Deinococcus-thermus	5
Bacteria	Dictyoglomi	1
Bacteria	Elusimicrobia	1
Bacteria	Cyanobacteria	10
Archaea/Archaea	Crenarchaeota	3
Archaea/Archaea	Korarchaeota	1
Bacteria	Verrucomicrobia	2
Bacteria	Planctomycetes	1
Archaea	Crenarchaeota	1
Bacteria	nah	1
Bacteria	Thermotogae	2
Bacteria	Nitrospirae	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0006555

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1073/pnas.91.13.5873. [PubMed:8016081 ]
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. doi: 10.1093/nar/28.6.1332. [PubMed:10684927 ]

Showing metabocard for DIMP (MMDBc0029837)

MOL for #<Metabolite:0x00007fe286d573f0>

3D MOL for #<Metabolite:0x00007fe286d573f0>

3D SDF for #<Metabolite:0x00007fe286d573f0>

3D-SDF for #<Metabolite:0x00007fe286d573f0>

PDB for #<Metabolite:0x00007fe286d573f0>

3D PDB for #<Metabolite:0x00007fe286d573f0>

SMILES for #<Metabolite:0x00007fe286d573f0>

INCHI for #<Metabolite:0x00007fe286d573f0>

Structure for #<Metabolite:0x00007fe286d573f0>

3D Structure for #<Metabolite:0x00007fe286d573f0>