NP-MRD: Showing NP-Card for Uridine 5'-monophosphate (NP0001301)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-07-01 14:27:35 UTC

NP-MRD ID

NP0001301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Uridine 5'-monophosphate

Description

Uridine 5'-monophosphate (UMP), also known as uridylic acid or uridylate, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. UMP consists of a phosphate group, a pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleotide monophosphate. Uridine 5'-monophosphate exists in all living species, ranging from bacteria to plants to humans. UMP is a nucleotide that is primarily used as a monomer in RNA biosynthesis. Uridine monophosphate is formed from Orotidine 5'-monophosphate (orotidylic acid) in a decarboxylation reaction catalyzed by the enzyme orotidylate decarboxylase. Within humans, uridine 5'-monophosphate participates in a number of enzymatic reactions. In particular, uridine 5'-monophosphate can be converted into uridine 5'-diphosphate through the action of the enzyme UMP-CMP kinase. In addition, uridine 5'-monophosphate can be biosynthesized from uridine 5'-diphosphate through its interaction with the enzyme soluble calcium-activated nucleotidase 1. In brain research studies, uridine monophosphate has been used as a convenient delivery compound for uridine. Uridine is present in many foods, mainly in the form of RNA. Non-phosphorylated uridine is not bioavailable beyond first-pass metabolism. In a study, gerbils fed a combination of uridine monophosphate, choline, and docosahexaenoic acid (DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function (PMID: 18606862 ).

Structure

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

HMDB0000288
     RDKit          3D
Uridine 5'-monophosphate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.6395    1.2168    2.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5807    0.8203    1.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.2808    2.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3954   -0.1327    1.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -0.0394    0.3224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0707   -0.4919   -0.2747 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0902   -0.1876    0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -0.8747   -0.2979 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4367   -0.6347    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7945    0.7008    0.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3658    0.9238    0.6693 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3675    0.7915    2.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4183   -0.2483    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565    2.4327    0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -0.2739   -1.6689 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1253   -1.1334   -2.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177   -0.0042   -1.6175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3130   -0.8393   -2.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3200    0.4898   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    0.6045   -1.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405    0.9081    0.3005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239    0.2047    3.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917   -0.5479    2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -1.6043   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -1.9454   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.9482    1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1347   -1.2785   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509   -0.5306    0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4127    3.1214    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3775    0.6384   -1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7328   -2.0462   -2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513    1.0532   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4555   -1.7406   -2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2370    1.3149   -0.2428 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  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
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
 17  6  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  6
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  6
 16 31  1  0
 17 32  1  6
 18 33  1  0
 21 34  1  0
M  END


  Mrv1652309032023592D          

 21 22  0  0  1  0            999 V2000
    0.4950    0.1203    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2822    0.3781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478    0.5912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509   -0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9009   -0.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4540    1.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8215    0.0997    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5741   -0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7356   -1.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915    0.0894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7393   -0.9762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2344    1.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052    0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0622   -1.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600    0.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1897   -0.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437    1.1550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0112   -0.2200    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0181   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8362   -0.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0181    0.6015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  1  0  0  0
  8 14  1  6  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
  7  8  1  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

> <INCHI_KEY>
DJJCXFVJDGTHFX-XVFCMESISA-N

> <FORMULA>
C9H13N2O9P

> <MOLECULAR_WEIGHT>
324.1813

> <EXACT_MASS>
324.035866536

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.295980635705423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.76

> <JCHEM_LOGP>
-2.538808173

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.251166930280792

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2255024716430984

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6645431498421583

> <JCHEM_POLAR_SURFACE_AREA>
165.85999999999999

> <JCHEM_REFRACTIVITY>
63.4385

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
uridine monophosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000288
     RDKit          3D
Uridine 5'-monophosphate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.6395    1.2168    2.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5807    0.8203    1.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.2808    2.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3954   -0.1327    1.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -0.0394    0.3224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0707   -0.4919   -0.2747 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0902   -0.1876    0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -0.8747   -0.2979 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4367   -0.6347    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7945    0.7008    0.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3658    0.9238    0.6693 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3675    0.7915    2.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4183   -0.2483    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565    2.4327    0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -0.2739   -1.6689 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1253   -1.1334   -2.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177   -0.0042   -1.6175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3130   -0.8393   -2.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3200    0.4898   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    0.6045   -1.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405    0.9081    0.3005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239    0.2047    3.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917   -0.5479    2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -1.6043   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -1.9454   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.9482    1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1347   -1.2785   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509   -0.5306    0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4127    3.1214    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3775    0.6384   -1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7328   -2.0462   -2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513    1.0532   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4555   -1.7406   -2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2370    1.3149   -0.2428 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  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
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
 17  6  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  6
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  6
 16 31  1  0
 17 32  1  6
 18 33  1  0
 21 34  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  C   UNK     0       0.924   0.225   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.393   0.706   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0      -0.276   1.104   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.468  -1.283   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.548  -0.321   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.714   2.214   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.533   0.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.072  -1.283   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.373  -2.522   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       5.024   0.167   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       3.247  -1.822   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.171   2.701   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.996   0.661   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.983  -2.515   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.339   1.675   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.087  -0.411   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.802   2.156   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0      -5.621  -0.411   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0      -5.634  -1.944   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -7.161  -0.411   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.634   1.123   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13    8                                                  
CONECT    8    4   14    7                                                  
CONECT    9    4                                                            
CONECT   10    5   15                                                       
CONECT   11    5                                                            
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    8                                                            
CONECT   15   10   17   12                                                  
CONECT   16   13   18                                                       
CONECT   17   15                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0000288
HETATM    1  O1  UNL     1      -5.640   1.217   2.204  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.581   0.820   1.633  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.520   0.281   2.337  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.395  -0.133   1.663  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.266  -0.039   0.322  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.071  -0.492  -0.275  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.090  -0.188   0.473  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.030  -0.875  -0.298  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.437  -0.635   0.178  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.794   0.701   0.131  1.00  0.00           O  
HETATM   11  P1  UNL     1       4.366   0.924   0.669  1.00  0.00           P  
HETATM   12  O4  UNL     1       4.368   0.792   2.179  1.00  0.00           O  
HETATM   13  O5  UNL     1       5.418  -0.248   0.025  1.00  0.00           O  
HETATM   14  O6  UNL     1       4.956   2.433   0.182  1.00  0.00           O  
HETATM   15  C7  UNL     1       0.781  -0.274  -1.669  1.00  0.00           C  
HETATM   16  O7  UNL     1       1.125  -1.133  -2.698  1.00  0.00           O  
HETATM   17  C8  UNL     1      -0.718  -0.004  -1.618  1.00  0.00           C  
HETATM   18  O8  UNL     1      -1.313  -0.839  -2.576  1.00  0.00           O  
HETATM   19  C9  UNL     1      -3.320   0.490  -0.315  1.00  0.00           C  
HETATM   20  O9  UNL     1      -3.266   0.605  -1.554  1.00  0.00           O  
HETATM   21  N2  UNL     1      -4.440   0.908   0.301  1.00  0.00           N  
HETATM   22  H1  UNL     1      -3.624   0.205   3.424  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.592  -0.548   2.254  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.089  -1.604  -0.315  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.816  -1.945  -0.358  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.487  -0.948   1.241  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.135  -1.279  -0.391  1.00  0.00           H  
HETATM   28  H7  UNL     1       6.051  -0.531   0.747  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.413   3.121   0.629  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.378   0.638  -1.745  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.733  -2.046  -2.571  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.851   1.053  -1.822  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.456  -1.741  -2.148  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.237   1.315  -0.243  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6   19
CONECT    6    7   17   24
CONECT    7    8
CONECT    8    9   15   25
CONECT    9   10   26   27
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   28
CONECT   14   29
CONECT   15   16   17   30
CONECT   16   31
CONECT   17   18   32
CONECT   18   33
CONECT   19   20   20   21
CONECT   21   34
END

HMDB0000288
     RDKit          3D
Uridine 5'-monophosphate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.6395    1.2168    2.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5807    0.8203    1.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.2808    2.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3954   -0.1327    1.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658   -0.0394    0.3224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0707   -0.4919   -0.2747 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0902   -0.1876    0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -0.8747   -0.2979 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4367   -0.6347    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7945    0.7008    0.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3658    0.9238    0.6693 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3675    0.7915    2.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4183   -0.2483    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565    2.4327    0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -0.2739   -1.6689 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1253   -1.1334   -2.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177   -0.0042   -1.6175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3130   -0.8393   -2.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3200    0.4898   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    0.6045   -1.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405    0.9081    0.3005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239    0.2047    3.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917   -0.5479    2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890   -1.6043   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162   -1.9454   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.9482    1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1347   -1.2785   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0509   -0.5306    0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4127    3.1214    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3775    0.6384   -1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7328   -2.0462   -2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513    1.0532   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4555   -1.7406   -2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2370    1.3149   -0.2428 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  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
  8 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
 17  6  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  6
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  6
 16 31  1  0
 17 32  1  6
 18 33  1  0
 21 34  1  0
M  END

View in JSmol

Synonyms

Value	Source
5'-UMP	ChEBI
5'Uridylic acid	ChEBI
pU	ChEBI
UMP	ChEBI
Uridine 5'-(dihydrogen phosphate)	ChEBI
Uridine 5'-phosphate	ChEBI
Uridine 5'-phosphoric acid	ChEBI
Uridine monophosphate	ChEBI
URIDINE-5'-monophosphATE	ChEBI
Uridylate	ChEBI
Uridylic acid	ChEBI
5'Uridylate	Generator
Uridine 5'-(dihydrogen phosphoric acid)	Generator
Uridine monophosphoric acid	Generator
URIDINE-5'-monophosphoric acid	Generator
Uridine 5'-monophosphoric acid	Generator
Uridine 5'-phosphorate	HMDB
Uridine mono(dihydrogen phosphate)	HMDB
Uridine phosphate	HMDB
Acids, uridylic	HMDB
monoPhosphate, uridine	HMDB
5'-monoPhosphate, uridine	HMDB
Uridylic acids	HMDB
Acid, uridylic	HMDB
Uridine 5' monophosphate	HMDB

Chemical Formula

C₉H₁₃N₂O₉P

Average Mass

324.1813 Da

Monoisotopic Mass

324.03587 Da

IUPAC Name

{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

uridine monophosphate

CAS Registry Number

58-97-9

SMILES

O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O

InChI Identifier

InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

InChI Key

DJJCXFVJDGTHFX-XVFCMESISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	KNApSAcK Database	22123792
Cannabis sativa	CannabisDB	Not Available
Daphnia pulex	LOTUS Database	35616633
Helianthus tuberosus	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Hyacinthoides non-scripta	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Mycoplasmopsis bovis	LOTUS Database	35616633
Ophiocordyceps sinensis	LOTUS Database	35616633
Synechococcus elongatus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Escherichia coli K12	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside monophosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
1,2-diol
Urea
Secondary alcohol
Lactam
Azacycle
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidine ribonucleoside 5'-monophosphate (CHEBI:16695 )
uridine 5'-phosphate (CHEBI:16695 )
Ribonucleotides (C00105 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	12 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.5	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	165.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	63.44 m³·mol⁻¹	ChemAxon
Polarizability	26.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000288

DrugBank ID

DB03685

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Uridine_monophosphate

METLIN ID

Not Available

PubChem Compound

6030

PDB ID

Not Available

ChEBI ID

16695

Good Scents ID

Not Available

References

General References

Munoz-Hoyos A, Molina-Carballo A, Macias M, Rodriguez-Cabezas T, Martin-Medina E, Narbona-Lopez E, Valenzuela-Ruiz A, Acuna-Castroviejo D: Comparison between tryptophan methoxyindole and kynurenine metabolic pathways in normal and preterm neonates and in neonates with acute fetal distress. Eur J Endocrinol. 1998 Jul;139(1):89-95. [PubMed:9703384 ]
Chiang EP, Bagley PJ, Roubenoff R, Nadeau M, Selhub J: Plasma pyridoxal 5'-phosphate concentration is correlated with functional vitamin B-6 indices in patients with rheumatoid arthritis and marginal vitamin B-6 status. J Nutr. 2003 Apr;133(4):1056-9. [PubMed:12672918 ]
Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Holguin S, Martinez J, Chow C, Wurtman R: Dietary uridine enhances the improvement in learning and memory produced by administering DHA to gerbils. FASEB J. 2008 Nov;22(11):3938-46. doi: 10.1096/fj.08-112425. Epub 2008 Jul 7. [PubMed:18606862 ]
Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44. doi: 10.1017/s0022029900021427. [PubMed:7196410 ]

Showing NP-Card for Uridine 5'-monophosphate (NP0001301)

MOL for NP0001301 (Uridine 5'-monophosphate)

3D MOL for NP0001301 (Uridine 5'-monophosphate)

3D SDF for NP0001301 (Uridine 5'-monophosphate)

3D-SDF for NP0001301 (Uridine 5'-monophosphate)

PDB for NP0001301 (Uridine 5'-monophosphate)

3D PDB for NP0001301 (Uridine 5'-monophosphate)

SMILES for NP0001301 (Uridine 5'-monophosphate)

INCHI for NP0001301 (Uridine 5'-monophosphate)

Structure for NP0001301 (Uridine 5'-monophosphate)

3D Structure for NP0001301 (Uridine 5'-monophosphate)