MiMeDB: Showing metabocard for Phosphoribosyl pyrophosphate (MMDBc0029489)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:24:22 UTC

Update Date

2022-08-31 10:32:00 UTC

Metabolite ID

MMDBc0029489

Metabolite Identification

Common Name

Phosphoribosyl pyrophosphate

Description

Phosphoribosyl pyrophosphate (PRPP) is a pentosephosphate. The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase. It plays a role in transferring phosphate groups in several reactions. (Wikipedia )

Structure

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

HMDB0000280
     RDKit          3D
Phosphoribosyl pyrophosphate
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.3328    2.8048   -0.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608    1.2932   -0.4426 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.1991    0.6555   -1.7609 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1385    0.8949    1.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968    0.6486   -0.3610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    0.7091    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -0.2233    1.1435 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0948    0.3785    0.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4376   -0.4602   -0.3932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5890   -1.0331    0.1375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7969    0.1447    0.0326 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1679    1.4880    0.3230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4037    0.0826   -1.5553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833   -0.1497    1.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    0.9286    0.6237 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.2893    1.1668    1.7460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    2.3768    0.1307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0839    0.2608   -0.7413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6153   -1.4557   -0.7660 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1250   -2.6621   -1.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114   -1.5565    0.5032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9151   -2.6129    1.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1183    0.4503   -1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0463   -0.0907    1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1662    0.4898    1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893    1.7393    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928   -0.3808    2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709    0.1415   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8527    0.7409   -2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3805    2.9641    0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9916   -0.7284   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.0099   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369   -3.0650   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840   -1.7271    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464   -3.2033    0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
  9 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21  7  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  1
  9 28  1  6
 13 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  6
 22 35  1  0
M  END


  Mrv1652309032023592D          

 22 22  0  0  0  0            999 V2000
 9998.969210000.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.254610000.1510    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.540010000.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6682 9999.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8431 9999.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.825310000.1510    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4382 9998.7115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2390 9999.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.108610000.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4138 9999.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.735110000.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2279 9998.7033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.450510000.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.163810000.5633    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10002.753510001.2766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.881310000.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.578210001.2766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.350210000.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.682810000.1600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9377 9999.3754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7627 9999.3754    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.017610000.1600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19  1  1  1  0  0  0
 20  7  1  1  0  0  0
 22 11  1  6  0  0  0
 21 12  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029489

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@H]1[C@@H](O)[C@@H](OP(O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1

> <INCHI_KEY>
PQGCEDQWHSBAJP-TXICZTDVSA-N

> <FORMULA>
C5H13O14P3

> <MOLECULAR_WEIGHT>
390.0696

> <EXACT_MASS>
389.95181466

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.459895654699924

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-2.971134817666666

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.7946491011714985

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0892767445547737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6809081734732274

> <JCHEM_POLAR_SURFACE_AREA>
229.73999999999998

> <JCHEM_REFRACTIVITY>
62.579600000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphoribosylpyrophosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000280
     RDKit          3D
Phosphoribosyl pyrophosphate
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.3328    2.8048   -0.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608    1.2932   -0.4426 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.1991    0.6555   -1.7609 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1385    0.8949    1.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968    0.6486   -0.3610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    0.7091    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -0.2233    1.1435 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0948    0.3785    0.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4376   -0.4602   -0.3932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5890   -1.0331    0.1375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7969    0.1447    0.0326 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1679    1.4880    0.3230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4037    0.0826   -1.5553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833   -0.1497    1.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    0.9286    0.6237 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.2893    1.1668    1.7460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    2.3768    0.1307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0839    0.2608   -0.7413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6153   -1.4557   -0.7660 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1250   -2.6621   -1.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114   -1.5565    0.5032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9151   -2.6129    1.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1183    0.4503   -1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0463   -0.0907    1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1662    0.4898    1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893    1.7393    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928   -0.3808    2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709    0.1415   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8527    0.7409   -2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3805    2.9641    0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9916   -0.7284   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.0099   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369   -3.0650   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840   -1.7271    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464   -3.2033    0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
  9 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21  7  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  1
  9 28  1  6
 13 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  6
 22 35  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0    8664.7438667.718   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0    8663.4098666.949   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0    8662.0758667.718   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8664.1818665.614   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8662.6408665.614   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0    8660.7418666.949   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0    8665.6188664.261   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8661.5138665.614   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8659.4038667.722   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8659.9728665.614   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8669.9068667.718   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8668.9598664.246   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8671.2418666.949   0.000  0.00  0.00           O+0
HETATM   14  P   UNK     0    8672.5728667.718   0.000  0.00  0.00           P+0
HETATM   15  O   UNK     0    8671.8078669.050   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8673.9128666.949   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8673.3468669.050   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8667.3208667.871   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8666.0758666.965   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.5508665.501   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.0908665.501   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.5668666.965   0.000  0.00  0.00           C+0
CONECT    1    2   19                                                       
CONECT    2    1    3    4    5                                             
CONECT    3    2    6                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    3    8    9   10                                             
CONECT    7   20                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11   13   22                                                       
CONECT   12   21                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   19   22                                                       
CONECT   19   20   18    1                                                  
CONECT   20   19   21    7                                                  
CONECT   21   20   22   12                                                  
CONECT   22   21   18   11                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0000280
HETATM    1  O1  UNL     1       4.333   2.805  -0.578  1.00  0.00           O  
HETATM    2  P1  UNL     1       4.361   1.293  -0.443  1.00  0.00           P  
HETATM    3  O2  UNL     1       5.199   0.656  -1.761  1.00  0.00           O  
HETATM    4  O3  UNL     1       5.139   0.895   1.005  1.00  0.00           O  
HETATM    5  O4  UNL     1       2.797   0.649  -0.361  1.00  0.00           O  
HETATM    6  C1  UNL     1       2.370   0.709   0.954  1.00  0.00           C  
HETATM    7  C2  UNL     1       1.181  -0.223   1.144  1.00  0.00           C  
HETATM    8  O5  UNL     1       0.095   0.379   0.558  1.00  0.00           O  
HETATM    9  C3  UNL     1      -0.438  -0.460  -0.393  1.00  0.00           C  
HETATM   10  O6  UNL     1      -1.589  -1.033   0.137  1.00  0.00           O  
HETATM   11  P2  UNL     1      -2.797   0.145   0.033  1.00  0.00           P  
HETATM   12  O7  UNL     1      -2.168   1.488   0.323  1.00  0.00           O  
HETATM   13  O8  UNL     1      -3.404   0.083  -1.555  1.00  0.00           O  
HETATM   14  O9  UNL     1      -4.083  -0.150   1.069  1.00  0.00           O  
HETATM   15  P3  UNL     1      -5.323   0.929   0.624  1.00  0.00           P  
HETATM   16  O10 UNL     1      -6.289   1.167   1.746  1.00  0.00           O  
HETATM   17  O11 UNL     1      -4.580   2.377   0.131  1.00  0.00           O  
HETATM   18  O12 UNL     1      -6.084   0.261  -0.741  1.00  0.00           O  
HETATM   19  C4  UNL     1       0.615  -1.456  -0.766  1.00  0.00           C  
HETATM   20  O13 UNL     1       0.125  -2.662  -1.220  1.00  0.00           O  
HETATM   21  C5  UNL     1       1.411  -1.556   0.503  1.00  0.00           C  
HETATM   22  O14 UNL     1       0.915  -2.613   1.247  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.118   0.450  -1.450  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.046  -0.091   1.140  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.166   0.490   1.684  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.989   1.739   1.170  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.993  -0.381   2.218  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.771   0.142  -1.274  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.853   0.741  -2.068  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.380   2.964   0.905  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.992  -0.728  -0.719  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.230  -1.010  -1.573  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.837  -3.065  -1.796  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.484  -1.727   0.233  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.346  -3.203   0.684  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    3   23
CONECT    4   24
CONECT    5    6
CONECT    6    7   25   26
CONECT    7    8   21   27
CONECT    8    9
CONECT    9   10   19   28
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   29
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   30
CONECT   18   31
CONECT   19   20   21   32
CONECT   20   33
CONECT   21   22   34
CONECT   22   35
END

HMDB0000280
     RDKit          3D
Phosphoribosyl pyrophosphate
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.3328    2.8048   -0.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608    1.2932   -0.4426 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.1991    0.6555   -1.7609 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1385    0.8949    1.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968    0.6486   -0.3610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    0.7091    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -0.2233    1.1435 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0948    0.3785    0.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4376   -0.4602   -0.3932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5890   -1.0331    0.1375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7969    0.1447    0.0326 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1679    1.4880    0.3230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4037    0.0826   -1.5553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833   -0.1497    1.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232    0.9286    0.6237 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.2893    1.1668    1.7460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    2.3768    0.1307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0839    0.2608   -0.7413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6153   -1.4557   -0.7660 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1250   -2.6621   -1.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114   -1.5565    0.5032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9151   -2.6129    1.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1183    0.4503   -1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0463   -0.0907    1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1662    0.4898    1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893    1.7393    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928   -0.3808    2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709    0.1415   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8527    0.7409   -2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3805    2.9641    0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9916   -0.7284   -0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.0099   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369   -3.0650   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840   -1.7271    0.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464   -3.2033    0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
  9 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21  7  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  1
  9 28  1  6
 13 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  6
 22 35  1  0
M  END

Synonyms

Value	Source
5-Phospho-alpha-D-ribose 1-diphosphate	ChEBI
5-Phosphoribosyl 1-pyrophosphate	ChEBI
5-Phosphoribosyl diphosphate	ChEBI
alpha-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)	ChEBI
ALPHA-PHOSPHORIBOSYLPYROphosphORIC ACID	ChEBI
Phosphoribosylpyrophosphate	ChEBI
PRib-PP	ChEBI
PRPP	ChEBI
5-Phospho-a-D-ribose 1-diphosphate	Generator
5-Phospho-a-D-ribose 1-diphosphoric acid	Generator
5-Phospho-alpha-D-ribose 1-diphosphoric acid	Generator
5-Phospho-α-D-ribose 1-diphosphate	Generator
5-Phospho-α-D-ribose 1-diphosphoric acid	Generator
5-Phosphoribosyl 1-pyrophosphoric acid	Generator
5-Phosphoribosyl diphosphoric acid	Generator
a-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)	Generator
a-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)	Generator
alpha-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)	Generator
Α-D-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)	Generator
Α-D-ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)	Generator
a-PHOSPHORIBOSYLPYROphosphate	Generator
a-PHOSPHORIBOSYLPYROphosphoric acid	Generator
alpha-PHOSPHORIBOSYLPYROphosphate	Generator
Α-phosphoribosylpyrophosphate	Generator
Α-phosphoribosylpyrophosphoric acid	Generator
Phosphoribosylpyrophosphoric acid	Generator
Phosphoribosyl pyrophosphoric acid	Generator
5-Phospho-a-D-ribose-1-diphosphate	HMDB
5-Phospho-a-D-ribosyl pyrophosphate	HMDB
5-Phospho-alpha-D-ribose-1-diphosphate	HMDB
5-Phospho-alpha-D-ribosyl pyrophosphate	HMDB
5-Phosphoribose 1-pyrophosphate	HMDB
5-Phosphoribosyl 1-diphosphate	HMDB
5-Phosphoribosyl a-1-pyrophosphate	HMDB
5-Phosphoribosyl-1-pyrophosphate	HMDB
5-Phosphorylribose 1-a-diphosphate	HMDB
5-Phosphorylribose 1-alpha-diphosphate	HMDB
5-Phosphorylribose 1-pyrophosphate	HMDB
5-Phosphorylribosyl 1-pyrophosphate	HMDB
a-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose	HMDB
a-D-5-Phosphoribosyl 1-pyrophosphate	HMDB
a-D-Ribofuranose 5-phosphate 1-pyrophosphate	HMDB
a-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)	HMDB
alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose	HMDB
alpha-D-5-Phosphoribosyl 1-pyrophosphate	HMDB
alpha-D-Ribofuranose 5-phosphate 1-pyrophosphate	HMDB
alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)	HMDB
Phosphoribosyl-1-pyrophosphate	HMDB
Phosphoribosyl-pyrophosphate	HMDB
Phosphoribosylpyrophosphorate	HMDB
PP-Ribose-p	HMDB
Pyrophosphate, phosphoribosyl	HMDB
5-Phospho-α-D-ribose-1-diphosphate	HMDB
5-Phospho-α-D-ribosyl pyrophosphate	HMDB
5-Phosphoribosyl alpha-1-pyrophosphate	HMDB
5-Phosphoribosyl pyrophosphate	HMDB
5-Phosphoribosyl α-1-pyrophosphate	HMDB
5-Phosphorylribose 1-α-diphosphate	HMDB
Α-D-5-phosphoribosyl 1-pyrophosphate	HMDB
Phosphoribosyl pyrophosphate	HMDB

Molecular Formula

C₅H₁₃O₁₄P₃

Average Mass

390.0696

Monoisotopic Mass

389.95181466

IUPAC Name

[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

Traditional Name

phosphoribosylpyrophosphate

CAS Registry Number

7540-64-9

SMILES

O[C@H]1[C@@H](O)[C@@H](OP(O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O

InChI Identifier

InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1

InChI Key

PQGCEDQWHSBAJP-TXICZTDVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Monosaccharide phosphate
Organic pyrophosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetrahydrofuran
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

5-O-phosphono-D-ribofuranosyl diphosphate (CHEBI:17111 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	-0.74	ALOGPS
logP	-3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.09	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	62.58 m³·mol⁻¹	ChemAxon
Polarizability	27.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-7902000000-513a0a03122b76d768d9	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-6952010000-eac4b7259ac1081ff665	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-000i-0009000000-4d49c2b254fa550d7fc4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-000i-0129000000-1d706d02a4abbeb42ed5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, negative	splash10-004u-0987000000-ea0ae1567abd90f10399	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-004l-0961000000-703b20987f54fa234a79	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, negative	splash10-004i-1930000000-0b45299b5f0eae24d372	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, negative	splash10-004i-2910000000-9ce95a1b1c6b6ca5768d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, negative	splash10-004i-6900000000-98e568c985ce119eab97	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 32V, negative	splash10-004i-9600000000-4d4d3c26cf4221488cb8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 38V, negative	splash10-004i-9300000000-ae7ce84c85a837e48257	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 45V, negative	splash10-004i-9100000000-535b36bb64043a2b5e66	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 54V, negative	splash10-004i-9000000000-b83900fdd755592d555a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-0006-0190000000-535b5f43d315fbc182ad	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-004i-9000000000-46d4cee1b5ac630ba9b8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-0a4i-0900000000-8f51c8c38a697fb3a6f0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-006x-0930000000-6eebf2cc9471f692be90	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, negative	splash10-01t9-7900000000-a94c6a883f36818a0855	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-00di-0089000000-73b944f3bcd8c2e5fa58	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-0udi-0079300000-a94093288821d386ab6a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0a4i-0001900000-04d2c9666f93d8bb3ec0	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01tc-2934000000-e0fcfd13254fd3781439	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dm-6593000000-b295e74d43b0dc625e47	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01r2-7920000000-a021603f22f19c083511	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0509000000-54231bd8f000ab2dd4a0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9301000000-447b996f7510c6ae354b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-54f70df2270a3e4f67d2	2015-09-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Erythrocyte
Feces
Fibroblasts

Tissue Locations

Erythrocyte
Fibroblasts

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192000	Amidophosphoribosyltransferase	Unknown	Q06203	Homo sapiens
MMDBp0192006	Nicotinate-nucleotide pyrophosphorylase [carboxylating]	Unknown	Q15274	Homo sapiens
MMDBp0192104	Adenine phosphoribosyltransferase	Enzyme	P07741	Homo sapiens
MMDBp0192133	Hypoxanthine-guanine phosphoribosyltransferase	Unknown	P00492	Homo sapiens
MMDBp0192212	Ribose-phosphate pyrophosphokinase 3	Unknown	P21108	Homo sapiens
MMDBp0192270	Ribose-phosphate pyrophosphokinase 1	Unknown	P60891	Homo sapiens
MMDBp0192274	Ribose-phosphate pyrophosphokinase 2	Unknown	P11908	Homo sapiens
MMDBp0192654	Uridine 5'-monophosphate synthase	Enzyme	P11172	Homo sapiens
MMDBp0195628	Nicotinamide phosphoribosyltransferase	Unknown	P43490	Homo sapiens
MMDBp0195640	Nicotinate phosphoribosyltransferase	Unknown	Q6XQN6	Homo sapiens
MMDBp0196271	Uracil phosphoribosyltransferase homolog	Enzyme	Q96BW1	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
NAD+ Signalling Pathway (Cancer)
NAD+ Signalling and Aging

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001763	Hydrogen Ion	Nicotinamide ribotide	Not Available	Nicotinamide Ribotide (NMN) Synthetase	VMH	30371894
MMDBr0001837	Orotidylic acid	Orotic acid	Uridine monophosphate synthetase	Orotate Phosphoribosyltransferase	VMH	30371894
MMDBr0002445	Adenosine monophosphate	Adenine	Adenine phosphoribosyltransferase	AMP:Pyrophosphate Phosphoribosyltransferase	VMH	30371894
MMDBr0002534	Nicotinic acid mononucleotide	Hydrogen Ion	Not Available	Nicotinate D-Ribonucleotide:Pyrophosphate Phosphoribosyltransferase	VMH	17604275
MMDBr0007052	Adenosine triphosphate	Pyrophosphate	Not Available	ATP phosphoribosyltransferase	VMH	30371894
MMDBr0007248	Adenine	Adenosine monophosphate	Not Available	Adenine Phosphoribosyltransferase	VMH	30371894
MMDBr0007263	2-Aminobenzoic acid	Pyrophosphate	Not Available	Anthranilate phosphoribosyltransferase	VMH	30371894
MMDBr0007460	Guanine	Guanosine monophosphate	Not Available	Guanine Phosphoribosyltransferase	VMH	30371894
MMDBr0007508	Hydrogen Ion	Carbon dioxide	Not Available	Nicotinate-Nucleotide Diphosphorylase (Carboxylating)	VMH	30371894
MMDBr0007516	Orotic acid	Orotidylic acid	Not Available	Orotidine-5'-phosphate pyrophosphate phosphoribosyltransferase	VMH	30371894
MMDBr0007547	Adenosine triphosphate	Adenosine monophosphate	Not Available	Phosphoribosylpyrophosphate Synthetase	VMH	30371894
MMDBr0007600	Pyrophosphate	Phosphoribosyl pyrophosphate	Not Available	Xanthine phosphoribosyltransferase, reversible	VMH	30371894
MMDBr0007646	Hydrogen Ion	Nicotinic acid mononucleotide	Not Available	NAPRTase	VMH	30371894
MMDBr0007833	L-Glutamine	L-Glutamic acid	Not Available	Glutamine Phosphoribosyldiphosphate Amidotransferase	VMH	30371894
MMDBr0007871	Hypoxanthine	Inosinic acid	Not Available	Hypoxanthine Phosphoribosyltransferase (Hypoxanthine)	VMH	30371894
MMDBr0007993	Phosphoribosyl pyrophosphate	Pyrophosphate	Not Available	Uracil phosphoribosyltransferase	VMH	30371894
MMDBr0010285	Phosphoribosyl pyrophosphate	Pyrophosphate	Uracil phosphoribosyltransferase homolog	Uracil Phosphoribosyltransferase	VMH	30371894
MMDBr0010293	Phosphoribosyl pyrophosphate	Pyrophosphate	Not Available	Xanthine Phosphoribosyltransferase	VMH	30371894
MMDBr0010884	Phosphoribosyl pyrophosphate	Pyrophosphate	Not Available	Xanthine phosphoribosyltransferase	VMH	30371894
MMDBr0012674	Adenosine triphosphate	ADP	Not Available	nicotinic acid mononucleotide pyrophosphorylase	VMH	30371894
MMDBr0012895	diphosphate	Phosphoribosyl pyrophosphate	Orotate phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0012896	Phosphoribosyl pyrophosphate	diphosphate	Orotate phosphoribosyltransferase 2	Transfer of a ribosyl group	RHEA	34755880
MMDBr0012943	diphosphate	Phosphoribosyl pyrophosphate	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0012944	Phosphoribosyl pyrophosphate	diphosphate	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0013038	diphosphate	Phosphoribosyl pyrophosphate	Tryptophan biosynthesis protein TrpCD	Transfer of a ribosyl group	RHEA	34755880
MMDBr0013039	Phosphoribosyl pyrophosphate	diphosphate	Anthranilate phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0013145	Carbon dioxide	Phosphoribosyl pyrophosphate	Probable nicotinate-nucleotide pyrophosphorylase [carboxylating]	Phosphorylation	RHEA	34755880
MMDBr0013146	Phosphoribosyl pyrophosphate	Carbon dioxide	Nicotinate-nucleotide pyrophosphorylase [carboxylating]	Phosphorylation	RHEA	34755880
MMDBr0013173	diphosphate	Phosphoribosyl pyrophosphate	Bifunctional protein PyrR	Transfer of phosphoribosyl group	RHEA	34755880
MMDBr0013174	Phosphoribosyl pyrophosphate	diphosphate	Uracil phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0013444	Adenosine triphosphate	Phosphoribosyl pyrophosphate	Ribose-phosphate pyrophosphokinase 1	Phosphorylation	RHEA	34755880
MMDBr0013549	Adenosine monophosphate	Phosphoribosyl pyrophosphate	Adenine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0013708	diphosphate	Phosphoribosyl pyrophosphate	Hypoxanthine-guanine phosphoribosyltransferase	Transfer of phosphoribosyl group; Synthesis	RHEA	34755880
MMDBr0013709	Phosphoribosyl pyrophosphate	diphosphate	Hypoxanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0013773	1-(5-phosphoribosyl)-ATP	Phosphoribosyl pyrophosphate	ATP phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0013958	Ribose 1,5-bisphosphate	Phosphoribosyl pyrophosphate	Ribose 1,5-bisphosphate phosphokinase PhnN	Phosphorylation	RHEA	34755880
MMDBr0014556	diphosphate	Phosphoribosyl pyrophosphate	Hypoxanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0014557	Phosphoribosyl pyrophosphate	diphosphate	Hypoxanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0015299	Phosphoribosyl pyrophosphate	5''-Phosphoribostamycin	Neamine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0015305	Phosphoribosyl pyrophosphate	diphosphate	Decaprenyl-phosphate phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0015450	4-Aminobenzoate	4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate	Beta-ribofuranosylphenol 5'-phosphate synthase	Synthesis	RHEA	34755880
MMDBr0015451	4-Aminobenzoate	4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate	Beta-ribofuranosylphenol 5'-phosphate synthase	Synthesis	RHEA	34755880
MMDBr0015480	Phosphoribosyl pyrophosphate	ADP	Probable nicotinate phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0016390	4-Hydroxybenzoic acid	4-(beta-D-ribofuranosyl)phenol 5'-phosphate	Beta-ribofuranosylphenol 5'-phosphate synthase	Synthesis	RHEA	34755880
MMDBr0016391	4-Hydroxybenzoic acid	4-(beta-D-ribofuranosyl)phenol 5'-phosphate	Beta-ribofuranosylphenol 5'-phosphate synthase	Synthesis	RHEA	34755880
MMDBr0017867	5-Phosphoribosylamine	Phosphoribosyl pyrophosphate	Amidophosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0018252	Hydrogen Ion	Phosphoribosyl-ATP	ATP phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0018280	2-Aminobenzoic acid	Pyrophosphate	Bifunctional protein TrpGD	Synthesis; Transfer of phosphoribosyl group	PathBank	31602464
MMDBr0018365	Hydrogen Ion	Carbon dioxide	Nicotinate-nucleotide pyrophosphorylase [carboxylating]	Phosphorylation	PathBank	31602464
MMDBr0018370	Nicotinic acid	Nicotinamide ribotide	Nicotinate phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0018502	Adenosine triphosphate	Hydrogen Ion	Ribose-phosphate pyrophosphokinase	Phosphorylation	PathBank	31602464
MMDBr0018504	Adenosine triphosphate	Phosphoribosyl pyrophosphate	Ribose 1,5-bisphosphate phosphokinase PhnN	Phosphorylation	PathBank	31602464
MMDBr0018505	L-Glutamine	L-Glutamic acid	Amidophosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0018615	Orotic acid	Orotidylic acid	Orotate phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019303	Hypoxanthine	Inosinic acid	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019306	Adenine	Adenosine monophosphate	Adenine phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019310	Guanine	Guanosine monophosphate	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019334	Xanthine	Xanthylic acid	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019572	Adenosine triphosphate	Hydrogen Ion	Ribose-phosphate pyrophosphokinase 1	Phosphorylation	PathBank	31602464
MMDBr0019574	Hydrogen Ion	Pyrophosphate	ATP phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019597	Hydrogen Ion	Carbon dioxide	Nicotinate-nucleotide pyrophosphorylase [carboxylating]	Phosphorylation	PathBank	31602464
MMDBr0019607	Nicotinic acid	Phosphate	Nicotinate phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019633	2-Aminobenzoic acid	Pyrophosphate	Anthranilate phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019788	Orotic acid	Orotidylic acid	Orotate phosphoribosyltransferase 2	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019835	L-Glutamine	L-Glutamic acid	Not Available		PathBank	31602464

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	560	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Lion ; Chicken ; Human subgingival plaque	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	523	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Metabolic reconstruction
Bacteria	Actinobacteria	183	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	133	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	15	Human feces; Human ; Pig	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	6		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	25	Human feces; Human ; Goat ; Pig	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	19		Metabolic reconstruction
Bacteria	Aquificae	4
Archaea/Archaea	Euryarchaeota	56		Metabolic reconstruction
Archaea/Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria	Chlamydiae	4	Cat ; Human
Bacteria	Chlorobi	11
Eukaryota/Fungi	Ascomycota	19	Human feces; Human saliva; Human supragingival plaque	Unknown
Eukaryota/Fungi	Basidiomycota	3
Bacteria	Deinococcus-thermus	7
Bacteria/NULL	Proteobacteria	3	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Lion ; Chicken ; Human subgingival plaque	Unknown; Metabolic reconstruction
Bacteria	Cyanobacteria	35	Human
Bacteria	nah	1
Bacteria	Thermotogae	10
Bacteria	Chloroflexi	10
Bacteria	Dictyoglomi	2
Bacteria	Elusimicrobia	2
Bacteria	Acidobacteria	3
Bacteria/NULL	Firmicutes	1	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Metabolic reconstruction
Bacteria/NULL	Actinobacteria	1	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Gemmatimonadetes	1
Bacteria	Nitrospirae	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	4.9	2.1	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	5.72	0.86	uM	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Erythrocyte	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000280

DrugBank ID

DB01632

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Phosphoribosyl pyrophosphate

METLIN ID

5274

PubChem Compound

7339

PDB ID

Not Available

ChEBI ID

17111

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Gorbach ZV: [Determination of phosphoribosyl pyrophosphate in the erythrocytes]. Lab Delo. 1977;(12):724-5. [PubMed:75318 ]
Nishida Y, Akaoka I, Nishizawa T, Maruki M, Maruki K: Synthesis and concentration of 5-phosphoribosyl-1-pyrophosphate in erythrocytes from patients with Down's syndrome. Ann Rheum Dis. 1977 Jun;36(3):261-3. doi: 10.1136/ard.36.3.261. [PubMed:141914 ]
Sperling O, Boer P, Brosh S, Elazar E, Szeinberg A, de Vries A: Normal activity of metabolic pathways involved in the formation and utilization of phosphoribosylpyrophosphate in erythrocytes of patients with primary metabolic gout. Nutr Metab. 1975;18(4):217-23. doi: 10.1159/000175597. [PubMed:172821 ]
Marcolongo R, Pompucci G, Micheli V: Familial distribution of increased erythrocyte PP-ribose-P levels. Adv Exp Med Biol. 1977;76A:280-6. doi: 10.1007/978-1-4613-4223-6_34. [PubMed:193371 ]
Blinov MN, Kamyshentsev MV, Luganova IS, Filanovskaia LI, Filippova VN: [Phosphoribosyl pyrophosphate and its metabolic enzymes in the erythrocytes in certain forms of anemia]. Vopr Med Khim. 1976 Jul-Aug;22(4):456-62. [PubMed:194412 ]
Tax WJ, Veerkamp JH: A simple and sensitive method for estimating the concentration and synthesis of 5-phosphoribosyl 1-pyrophosphate in red blood cells. Clin Chim Acta. 1977 Jul 15;78(2):209-16. doi: 10.1016/0009-8981(77)90308-4. [PubMed:195752 ]
Emmerson BT, Gordon RB, Thompson L: Adenine phosphoribosyltransferase deficiency: its inheritance and occurrence in a female with gout and renal disease. Aust N Z J Med. 1975 Oct;5(5):440-6. doi: 10.1111/j.1445-5994.1975.tb03054.x. [PubMed:1061547 ]
Sakuma R, Nishina T, Yamanaka H, Kamatani N, Nishioka K, Maeda M, Tsuji A: Phosphoribosylpyrophosphate synthetase in human erythrocytes: assay and kinetic studies using high-performance liquid chromatography. Clin Chim Acta. 1991 Dec 16;203(2-3):143-52. doi: 10.1016/0009-8981(91)90286-l. [PubMed:1663846 ]
Gordon RB, Keough DT, Emmerson BT: HPRT-deficiency associated with normal PRPP concentration and APRT activity. J Inherit Metab Dis. 1987;10(1):82-8. doi: 10.1007/BF01799493. [PubMed:2437388 ]
Rylance HJ, Wallace RC, Nuki G: A method for the determination of 5-phosphoribosyl 1-pyrophosphate concentrations in erythrocytes using high-performance liquid chromatography. Anal Biochem. 1987 Feb 1;160(2):337-41. doi: 10.1016/0003-2697(87)90056-x. [PubMed:2437821 ]
Ghitis J, Schreiber C, Waxman S: Phosphate-induced phosphoribosylpyrophosphate elevations to assess deranged folate and purine nucleotide metabolism. Proc Soc Exp Biol Med. 1987 Oct;186(1):90-5. doi: 10.3181/00379727-186-42590. [PubMed:2442765 ]
Kane MA, Roth E, Raptis G, Schreiber C, Waxman S: Effect of intracellular folate concentration on the modulation of 5-fluorouracil cytotoxicity by the elevation of phosphoribosylpyrophosphate in cultured human KB cells. Cancer Res. 1987 Dec 15;47(24 Pt 1):6444-50. [PubMed:2445472 ]
Snyder FF, Dyer C, Seegmiller JE, Goldblum RM, Mills GC, Schmalstieg FC: Substrate inhibition of adenosine phosphorylation in adenosine deaminase deficiency and adenosine-mediated inhibition of PP-ribose-P dependent nucleotide synthesis in hypoxanthine phosphoribosyltransferase deficient erythrocytes. J Inherit Metab Dis. 1988;11(2):174-83. doi: 10.1007/BF01799869. [PubMed:2459496 ]
Lachant NA, Zerez CR, Tanaka KR: Pyrimidine nucleotides impair phosphoribosylpyrophosphate (PRPP) synthetase subunit aggregation by sequestering magnesium. A mechanism for the decreased PRPP synthetase activity in hereditary erythrocyte pyrimidine 5'-nucleotidase deficiency. Biochim Biophys Acta. 1989 Jan 19;994(1):81-8. doi: 10.1016/0167-4838(89)90065-4. [PubMed:2535789 ]
Zerez CR, Lachant NA, Tanaka KR: Decreased erythrocyte phosphoribosylpyrophosphate synthetase activity and impaired formation in thalassemia minor: a mechanism for decreased adenine nucleotide content. J Lab Clin Med. 1989 Jul;114(1):43-50. [PubMed:2544652 ]
Becker MA, Losman MJ, Itkin P, Simkin PA: Gout with superactive phosphoribosylpyrophosphate synthetase due to increased enzyme catalytic rate. J Lab Clin Med. 1982 Apr;99(4):495-511. [PubMed:6174658 ]
Micheli V, Taddeo A: [Spectrophotometric assay of 5-phosphoribosyl-1-pyrophosphate synthetase (PRPP) in erythrocyte lysate (author's transl)]. Quad Sclavo Diagn. 1981 Jun;17(2):209-15. [PubMed:6267652 ]
MacDermot KD, Allsop J, Watts RW: The rate of purine synthesis de nova in blood mononuclear cells in vitro from patients with familial hyperuricaemic nephropathy. Clin Sci (Lond). 1984 Aug;67(2):249-58. doi: 10.1042/cs0670249. [PubMed:6744792 ]
Zoref-Shani E, Feinstein S, Frishberg Y, Bromberg Y, Sperling O: Kelley-Seegmiller syndrome due to a unique variant of hypoxanthine-guanine phosphoribosyltransferase: reduced affinity for 5-phosphoribosyl-1-pyrophosphate manifested only at low, physiological substrate concentrations. Biochim Biophys Acta. 2000 Feb 21;1500(2):197-203. doi: 10.1016/s0925-4439(99)00103-9. [PubMed:10657589 ]
Yamaoka T, Yano M, Kondo M, Sasaki H, Hino S, Katashima R, Moritani M, Itakura M: Feedback inhibition of amidophosphoribosyltransferase regulates the rate of cell growth via purine nucleotide, DNA, and protein syntheses. J Biol Chem. 2001 Jun 15;276(24):21285-91. doi: 10.1074/jbc.M011103200. Epub 2001 Apr 4. [PubMed:11290738 ]

Showing metabocard for Phosphoribosyl pyrophosphate (MMDBc0029489)

MOL for #<Metabolite:0x00007f5a9c59bc00>

3D MOL for #<Metabolite:0x00007f5a9c59bc00>

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Structure for #<Metabolite:0x00007f5a9c59bc00>

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