MiMeDB: Showing metabocard for Nicotinamide ribotide (MMDBc0029484)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:24:09 UTC

Update Date

2022-08-31 10:31:39 UTC

Metabolite ID

MMDBc0029484

Metabolite Identification

Common Name

Nicotinamide ribotide

Description

Nicotinamide ribotide (NMN) is an important intermediate metabolite in the nicotinate and nicotinamide metabolism pathway. Nicotinamide is directly converted to NMN by nicotinamide phosphoribosyltransferase (NAMPT, EC 2.4.2.12). The enzyme nicotinamide mononucleotide adenylyltransferase (NMNAT, EC 2.7.7.1), a member of the nucleotidyltransferase alpha/beta-phosphodiesterase superfamily, catalyzes the reaction NMN + ATP = Nicotinamide adenine dinucleotide (NAD) + PPi, representing the final step in the biosynthesis of NAD, a molecule playing a fundamental role as a cofactor in cellular redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis, and circulating NMN levels may play an important role in regulating cell function in physiological and pathophysiological conditions. (PMID: 15078171 , 17983582 )

Structure

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

HMDB0001132
     RDKit          3D
Nicotinic acid mononucleotide
 37 38  0  0  0  0  0  0  0  0999 V2000
    5.3723   -0.6660    1.4109 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416    0.0560    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862    0.6984   -0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002    0.2038   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356    0.9999   -1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260    1.1003   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6915    0.4445   -1.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7689   -0.3134   -0.5959 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.6225   -1.0308   -0.0831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4104   -1.1077   -0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897   -1.2665   -0.3133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6459   -0.2635   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8353   -0.4874   -0.0334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379    0.5848   -0.4818 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.4214    0.3592   -1.9462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5098    2.1934   -0.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3709    0.3299    0.5183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3431   -1.0270    1.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0764   -2.2287    1.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043   -0.2808    1.0916 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7223   -0.4196    2.2510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -0.4250    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6394    1.6965    0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9240    1.5139   -1.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609    1.7239   -3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374    0.5254   -2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194   -2.0161    0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -2.2980   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -0.4099   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2803    0.7600   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2413    2.7422    0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9770    1.1251    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -0.4260    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710   -2.5691    2.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    0.7588    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801    0.4712    2.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -1.0521    0.9434 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 11 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  8 22  2  0
 22  4  1  0
 20  9  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  1
 11 28  1  1
 12 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  1
 19 34  1  0
 20 35  1  6
 21 36  1  0
 22 37  1  0
M  CHG  1   8   1
M  END


  Mrv1652305012018142D          

 22 23  0  0  0  0            999 V2000
 9999.478110001.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.271510001.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7382 9999.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.454910000.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.819510000.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1695 9999.6744    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1037 9999.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.819510000.9126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.7585 9998.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.886210000.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5847 9998.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.252110000.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5377 9999.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5377 9998.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2521 9998.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9666 9998.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9666 9999.6733    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10000.3565 9999.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.689110000.0786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.944010000.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.769010000.8632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.023910000.0786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
 13  5  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
 20  1  1  6  0  0  0
 19 17  1  1  0  0  0
 21  2  1  6  0  0  0
 22  3  1  1  0  0  0
M  CHG  1  17   1
M  END
> <DATABASE_ID>
MMDBc0029484

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)[N+]1=CC=CC(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-4,7-10,13-14H,5H2,(H2-,15,16,17,18,19)/p+1/t7-,8-,9-,10-/m1/s1

> <INCHI_KEY>
JOUIQRNQJGXQDC-ZYUZMQFOSA-O

> <FORMULA>
C11H15NO9P

> <MOLECULAR_WEIGHT>
336.2119

> <EXACT_MASS>
336.048442595

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.664880155700757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium

> <ALOGPS_LOGP>
-0.99

> <JCHEM_LOGP>
-5.437405301471745

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.769972865112575

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.200840941351724

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7319661030900226

> <JCHEM_POLAR_SURFACE_AREA>
157.63000000000002

> <JCHEM_REFRACTIVITY>
69.8852

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001132
     RDKit          3D
Nicotinic acid mononucleotide
 37 38  0  0  0  0  0  0  0  0999 V2000
    5.3723   -0.6660    1.4109 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416    0.0560    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862    0.6984   -0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002    0.2038   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356    0.9999   -1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260    1.1003   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6915    0.4445   -1.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7689   -0.3134   -0.5959 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.6225   -1.0308   -0.0831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4104   -1.1077   -0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897   -1.2665   -0.3133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6459   -0.2635   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8353   -0.4874   -0.0334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379    0.5848   -0.4818 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.4214    0.3592   -1.9462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5098    2.1934   -0.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3709    0.3299    0.5183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3431   -1.0270    1.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0764   -2.2287    1.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043   -0.2808    1.0916 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7223   -0.4196    2.2510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -0.4250    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6394    1.6965    0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9240    1.5139   -1.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609    1.7239   -3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374    0.5254   -2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194   -2.0161    0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -2.2980   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -0.4099   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2803    0.7600   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2413    2.7422    0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9770    1.1251    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -0.4260    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710   -2.5691    2.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    0.7588    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801    0.4712    2.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -1.0521    0.9434 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 11 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  8 22  2  0
 22  4  1  0
 20  9  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  1
 11 28  1  1
 12 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  1
 19 34  1  0
 20 35  1  6
 21 36  1  0
 22 37  1  0
M  CHG  1   8   1
M  END

HEADER    PROTEIN                                 01-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-20         0                                  
HETATM    1  O   UNK     0    8665.6928669.535   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8669.0408669.519   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.9118666.059   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8671.2498666.828   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8660.7308666.828   0.000  0.00  0.00           C+0
HETATM    6  P   UNK     0    8672.5838666.059   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0    8659.3948666.059   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8660.7308668.370   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8671.8168664.723   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8673.9218666.828   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8673.3588664.723   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8663.4048666.827   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.0708666.057   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.0708664.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.4048663.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.7388664.517   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8664.7388666.057   0.000  0.00  0.00           N+1
HETATM   18  O   UNK     0    8667.3328665.908   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8666.0868666.813   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.5628668.278   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.1028668.278   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.5788666.813   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4   22                                                       
CONECT    4    3    6                                                       
CONECT    5    7    8   13                                                  
CONECT    6    4    9   10   11                                             
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14    5                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   19                                                  
CONECT   18   19   22                                                       
CONECT   19   20   18   17                                                  
CONECT   20   19   21    1                                                  
CONECT   21   20   22    2                                                  
CONECT   22   21   18    3                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0001132
HETATM    1  O1  UNL     1       5.372  -0.666   1.411  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.342   0.056   0.396  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.486   0.698  -0.014  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.100   0.204  -0.332  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.036   1.000  -1.464  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.826   1.100  -2.113  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.691   0.445  -1.680  1.00  0.00           C  
HETATM    8  N1  UNL     1       1.769  -0.313  -0.596  1.00  0.00           N1+
HETATM    9  C6  UNL     1       0.622  -1.031  -0.083  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.410  -1.108  -0.979  1.00  0.00           O  
HETATM   11  C7  UNL     1      -1.590  -1.267  -0.313  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.646  -0.264  -0.763  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.835  -0.487  -0.033  1.00  0.00           O  
HETATM   14  P1  UNL     1      -5.038   0.585  -0.482  1.00  0.00           P  
HETATM   15  O5  UNL     1      -5.421   0.359  -1.946  1.00  0.00           O  
HETATM   16  O6  UNL     1      -4.510   2.193  -0.258  1.00  0.00           O  
HETATM   17  O7  UNL     1      -6.371   0.330   0.518  1.00  0.00           O  
HETATM   18  C9  UNL     1      -1.343  -1.027   1.157  1.00  0.00           C  
HETATM   19  O8  UNL     1      -1.076  -2.229   1.839  1.00  0.00           O  
HETATM   20  C10 UNL     1      -0.004  -0.281   1.092  1.00  0.00           C  
HETATM   21  O9  UNL     1       0.722  -0.420   2.251  1.00  0.00           O  
HETATM   22  C11 UNL     1       2.940  -0.425   0.052  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.639   1.697   0.055  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.924   1.514  -1.803  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.761   1.724  -3.005  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.737   0.525  -2.194  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.919  -2.016   0.310  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.970  -2.298  -0.502  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.914  -0.410  -1.830  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.280   0.760  -0.610  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.241   2.742   0.110  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.977   1.125   0.525  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.108  -0.426   1.647  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.871  -2.569   2.313  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.252   0.759   0.839  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.980   0.471   2.610  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.990  -1.052   0.943  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5    5   22
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9   22   22
CONECT    9   10   20   27
CONECT   10   11
CONECT   11   12   18   28
CONECT   12   13   29   30
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   16   31
CONECT   17   32
CONECT   18   19   20   33
CONECT   19   34
CONECT   20   21   35
CONECT   21   36
CONECT   22   37
END

HMDB0001132
     RDKit          3D
Nicotinic acid mononucleotide
 37 38  0  0  0  0  0  0  0  0999 V2000
    5.3723   -0.6660    1.4109 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416    0.0560    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862    0.6984   -0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002    0.2038   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356    0.9999   -1.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260    1.1003   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6915    0.4445   -1.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7689   -0.3134   -0.5959 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.6225   -1.0308   -0.0831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4104   -1.1077   -0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897   -1.2665   -0.3133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6459   -0.2635   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8353   -0.4874   -0.0334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379    0.5848   -0.4818 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.4214    0.3592   -1.9462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5098    2.1934   -0.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3709    0.3299    0.5183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3431   -1.0270    1.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0764   -2.2287    1.8390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043   -0.2808    1.0916 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7223   -0.4196    2.2510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -0.4250    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6394    1.6965    0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9240    1.5139   -1.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609    1.7239   -3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374    0.5254   -2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194   -2.0161    0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -2.2980   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -0.4099   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2803    0.7600   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2413    2.7422    0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9770    1.1251    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -0.4260    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710   -2.5691    2.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    0.7588    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801    0.4712    2.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -1.0521    0.9434 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 11 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  8 22  2  0
 22  4  1  0
 20  9  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  1
 11 28  1  1
 12 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  1
 19 34  1  0
 20 35  1  6
 21 36  1  0
 22 37  1  0
M  CHG  1   8   1
M  END

Synonyms

Value	Source
beta-Nicotinate D-ribonucleotide	ChEBI
Nicotinate ribonucleotide	ChEBI
Nicotinic acid ribonucleotide	ChEBI
b-Nicotinate D-ribonucleotide	Generator
b-Nicotinic acid D-ribonucleotide	Generator
beta-Nicotinic acid D-ribonucleotide	Generator
β-Nicotinate D-ribonucleotide	Generator
β-Nicotinic acid D-ribonucleotide	Generator
Nicotinic acid D-ribonucleotide	Generator
Nicotinate D-ribonucleotide	ChEBI
Nicotinate b-D-ribonucleotide	Generator
Nicotinate β-D-ribonucleotide	Generator
Nicotinic acid b-D-ribonucleotide	Generator
Nicotinic acid beta-D-ribonucleotide	Generator
Nicotinic acid β-D-ribonucleotide	Generator
Nicotinate mononucleotide	MeSH
Nicotinic acid mononucleotide	MeSH
Deamido nicotinamide ribonucleotide	HMDB
Deamido-NMN	HMDB
Nicotinic acid ribotide	HMDB
Nicotinic mononucleotide	HMDB
beta-Nicotinic acid mononucleotide	HMDB
β-Nicotinic acid mononucleotide	HMDB

Molecular Formula

C₁₁H₁₅NO₉P

Average Mass

336.2119

Monoisotopic Mass

336.048442595

IUPAC Name

3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium

Traditional Name

3-carboxy-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium

CAS Registry Number

1094-61-7

SMILES

O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)[N+]1=CC=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C11H14NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-4,7-10,13-14H,5H2,(H2-,15,16,17,18,19)/p+1/t7-,8-,9-,10-/m1/s1

InChI Key

JOUIQRNQJGXQDC-ZYUZMQFOSA-O

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as nicotinic acid nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinic acid or a derivative thereof.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyridine nucleotides

Sub Class

Nicotinic acid nucleotides

Direct Parent

Nicotinic acid nucleotides

Alternative Parents

Substituents

Nicotinic-acid-nucleotide
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Pyridine
Pyridinium
Alkyl phosphate
Vinylogous amide
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
1,2-diol
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Alcohol
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nicotinic acid mononucleotide (CHEBI:15763 )
Pyridine alkaloids (C01185 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.71 g/L	ALOGPS
logP	-0.99	ALOGPS
logP	-5.4	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.2	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	157.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.89 m³·mol⁻¹	ChemAxon
Polarizability	28.66 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-9704000000-b4f3d91df4a5fb88cc5e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-000b-9221310000-f2425a1cc55147b91d2b	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1009000000-227e6a4729b96a705fa4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-5239000000-223d08e3fd97af58d374	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9500000000-db23a80f58b7ac9781fd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1009000000-f16974a59d3ff46358d6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-9001000000-ca67d776dd7d3f5d4650	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-5808f9bb378f2d60cd9b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0479000000-61da4c1926ec7950c051	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00si-5950000000-2c01c6fd1632660b38c7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9500000000-3dbb0f51364659db892e	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Nucleus

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
MMDBp0191677	5'-nucleotidase	Unknown	P21589	Homo sapiens
MMDBp0191680	Cytosolic 5'-nucleotidase 1B	Unknown	Q96P26	Homo sapiens
MMDBp0191681	Cytosolic 5'-nucleotidase 1A	Unknown	Q9BXI3	Homo sapiens
MMDBp0191682	5'(3')-deoxyribonucleotidase, cytosolic type	Unknown	Q8TCD5	Homo sapiens
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo sapiens
MMDBp0191790	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Unknown	P22413	Homo sapiens
MMDBp0191865	Ectonucleotide pyrophosphatase/phosphodiesterase family member 3	Unknown	O14638	Homo sapiens
MMDBp0192004	Nicotinamide mononucleotide adenylyltransferase 1	Unknown	Q9HAN9	Homo sapiens
MMDBp0192005	Nicotinamide mononucleotide adenylyltransferase 3	Unknown	Q96T66	Homo sapiens
MMDBp0192006	Nicotinate-nucleotide pyrophosphorylase [carboxylating]	Unknown	Q15274	Homo sapiens
MMDBp0192007	Nicotinamide mononucleotide adenylyltransferase 2	Unknown	Q9BZQ4	Homo sapiens
MMDBp0193860	Cytosolic 5'-nucleotidase 3	Enzyme	Q9H0P0	Homo sapiens
MMDBp0193932	Cytosolic purine 5'-nucleotidase	Unknown	P49902	Homo sapiens
MMDBp0193958	Nicotinamide riboside kinase 1	Unknown	Q9NWW6	Homo sapiens
MMDBp0194179	Peroxisomal NADH pyrophosphatase NUDT12	Unknown	Q9BQG2	Homo sapiens
MMDBp0195629	Nicotinamide riboside kinase 2	Unknown	Q9NPI5	Homo sapiens
MMDBp0195640	Nicotinate phosphoribosyltransferase	Unknown	Q6XQN6	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001763	Niacinamide	Nicotinamide ribotide	Not Available	VMH; KEGG	30371894
MMDBr0002083	Nicotinamide riboside	Nicotinamide ribotide	nicotinamide riboside kinase 1	VMH; KEGG	30371894
MMDBr0002584	Nicotinamide ribotide	Nicotinic acid mononucleotide	Not Available	VMH	7021549
MMDBr0007914	Nicotinamide ribotide	Nicotinamide riboside	Not Available	VMH	30371894
MMDBr0007923	Nicotinamide ribotide	Nicotinamide riboside	Not Available	VMH	30371894
MMDBr0012675	Nicotinamide ribotide	Nicotinic acid mononucleotide	Not Available	VMH	30371894

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	182	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	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	390	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	Metabolic reconstruction
Bacteria	Actinobacteria	128	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	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human supragingival plaque; Human subgingival plaque; Human gastric fluid; Human urine	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

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

HMDB0001132

DrugBank ID

DB02382

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

NICOTINATE_NUCLEOTIDE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121992

PDB ID

Not Available

ChEBI ID

15763

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for Nicotinamide ribotide (MMDBc0029484)

MOL for #<Metabolite:0x00007fece48da7d8>

3D MOL for #<Metabolite:0x00007fece48da7d8>

3D SDF for #<Metabolite:0x00007fece48da7d8>

3D-SDF for #<Metabolite:0x00007fece48da7d8>

PDB for #<Metabolite:0x00007fece48da7d8>

3D PDB for #<Metabolite:0x00007fece48da7d8>

SMILES for #<Metabolite:0x00007fece48da7d8>

INCHI for #<Metabolite:0x00007fece48da7d8>

Structure for #<Metabolite:0x00007fece48da7d8>

3D Structure for #<Metabolite:0x00007fece48da7d8>