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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (16) Show 16 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:57:20 UTC

HMDB ID

HMDB0000229

Secondary Accession Numbers

HMDB00229
HMDB0059645
HMDB59645

Metabolite Identification

Common Name

Nicotinamide ribotide

Description

Nicotinamide ribotide (NMN) (CAS: 1094-61-7) is an important intermediate metabolite in the nicotinate and nicotinamide metabolism pathway. Mammals predominantly use nicotinamide rather than nicotinic acid as a precursor for NAD biosynthesis. Instead of the deamidation into nicotinic acid, nicotinamide is directly converted into NMN by nicotinamide phosphoribosyltransferase (NAMPT, EC 2.4.2.12). The enzyme nicotinamide mononucleotide adenylyltransferase (NMNAT, EC 2.7.7.1), which is 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. NAD is a molecule that plays a fundamental role as a cofactor in cellular redox reactions. Thus NMN is an important metabolite for the maintenance of normal NAD biosynthesis. 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

HMDB0000229
     RDKit          3D
Nicotinamide ribotide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -5.7549    1.3793    1.9028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6572    1.4678    1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124    2.4829    0.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6768    0.3820    0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8428   -0.7400    1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8935   -1.7364    1.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278   -1.6014    0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.5044    0.0006 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.5431   -0.4392   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5665   -1.1241   -0.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6267   -0.7436   -1.1606 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9363   -0.7035   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -0.3065   -1.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426   -0.2260   -0.5512 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3310    0.0251    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    1.0566   -1.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2595   -1.6798   -0.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515    0.6154   -1.7121 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0777    0.4861   -3.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171    0.9583   -1.0356 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6899    1.7290   -1.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    0.4668    0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6466    0.8792    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6793    1.8556    2.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6844   -0.8339    2.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381   -2.6137    2.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0988   -2.4033    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133   -0.7901   -1.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -1.5220   -1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790   -0.0677    0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -1.7265   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140    1.9263   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -2.3324   -0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263    1.3624   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932   -0.4305   -3.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804    1.4351   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    2.6748   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4887    1.3423   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  6
 19 35  1  0
 20 36  1  1
 21 37  1  0
 22 38  1  0
M  CHG  1   8   1
M  END


  Mrv1652307172022332D          

 22 23  0  0  0  0            999 V2000
 9999.478310001.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.266810001.5298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7347 9999.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.447810000.0912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.825810000.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1651 9999.6802    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1116 9999.6802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.825810000.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.7508 9998.9658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.878310000.0912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5753 9998.9658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.255010000.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5406 9999.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5406 9998.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2550 9998.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9695 9998.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9695 9999.6799    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10000.3551 9999.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.022510000.0820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.767610000.8666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.942610000.8666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.687710000.0820    0.0000 C   0  0  2  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
 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
 21  1  1  6  0  0  0
 20  2  1  6  0  0  0
 19  3  1  1  0  0  0
 22 17  1  1  0  0  0
 13  5  1  0  0  0  0
M  CHG  1  17   1
M  END
> <DATABASE_ID>
HMDB0000229

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/p+1/t7-,8-,9-,11-/m1/s1

> <INCHI_KEY>
DAYLJWODMCOQEW-TURQNECASA-O

> <FORMULA>
C11H16N2O8P

> <MOLECULAR_WEIGHT>
335.2271

> <EXACT_MASS>
335.06442701

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.046815469947326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.50

> <JCHEM_LOGP>
-6.244347915138411

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.238873946004625

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2136795738389177

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6275786986158498

> <JCHEM_POLAR_SURFACE_AREA>
163.41999999999996

> <JCHEM_REFRACTIVITY>
71.70739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000229
     RDKit          3D
Nicotinamide ribotide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -5.7549    1.3793    1.9028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6572    1.4678    1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124    2.4829    0.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6768    0.3820    0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8428   -0.7400    1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8935   -1.7364    1.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278   -1.6014    0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.5044    0.0006 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.5431   -0.4392   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5665   -1.1241   -0.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6267   -0.7436   -1.1606 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9363   -0.7035   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -0.3065   -1.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426   -0.2260   -0.5512 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3310    0.0251    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    1.0566   -1.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2595   -1.6798   -0.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515    0.6154   -1.7121 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0777    0.4861   -3.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171    0.9583   -1.0356 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6899    1.7290   -1.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    0.4668    0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6466    0.8792    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6793    1.8556    2.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6844   -0.8339    2.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381   -2.6137    2.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0988   -2.4033    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133   -0.7901   -1.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -1.5220   -1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790   -0.0677    0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -1.7265   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140    1.9263   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -2.3324   -0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263    1.3624   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932   -0.4305   -3.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804    1.4351   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    2.6748   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4887    1.3423   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  6
 19 35  1  0
 20 36  1  1
 21 37  1  0
 22 38  1  0
M  CHG  1   8   1
M  END

HEADER    PROTEIN                                 17-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-20         0                                  
HETATM    1  O   UNK     0    8665.6938669.538   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8669.0318669.522   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.9058666.070   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8671.2368666.837   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8660.7418666.837   0.000  0.00  0.00           C+0
HETATM    6  P   UNK     0    8672.5758666.070   0.000  0.00  0.00           P+0
HETATM    7  N   UNK     0    8659.4088666.070   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8660.7418668.376   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8671.8018664.736   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8673.9068666.837   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8673.3418664.736   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8663.4098666.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.0768666.069   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.0768664.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.4098663.759   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.7438664.529   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8664.7438666.069   0.000  0.00  0.00           N+1
HETATM   18  O   UNK     0    8667.3308665.914   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8668.5758666.820   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.1008668.284   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.5608668.284   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.0848666.820   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   20                                                            
CONECT    3    4   19                                                       
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   22                                                  
CONECT   18   19   22                                                       
CONECT   19   20   18    3                                                  
CONECT   20   19   21    2                                                  
CONECT   21   20   22    1                                                  
CONECT   22   21   18   17                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0000229
HETATM    1  N1  UNL     1      -5.755   1.379   1.903  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.657   1.468   1.040  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.512   2.483   0.333  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.677   0.382   0.957  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.843  -0.740   1.743  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.893  -1.736   1.631  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.828  -1.601   0.764  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.672  -0.504   0.001  1.00  0.00           N1+
HETATM    9  C6  UNL     1      -0.543  -0.439  -0.871  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.567  -1.124  -0.379  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.627  -0.744  -1.161  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.936  -0.704  -0.399  1.00  0.00           C  
HETATM   13  O3  UNL     1       3.941  -0.306  -1.285  1.00  0.00           O  
HETATM   14  P1  UNL     1       5.443  -0.226  -0.551  1.00  0.00           P  
HETATM   15  O4  UNL     1       5.331   0.025   0.934  1.00  0.00           O  
HETATM   16  O5  UNL     1       6.306   1.057  -1.228  1.00  0.00           O  
HETATM   17  O6  UNL     1       6.260  -1.680  -0.809  1.00  0.00           O  
HETATM   18  C9  UNL     1       1.352   0.615  -1.712  1.00  0.00           C  
HETATM   19  O7  UNL     1       1.078   0.486  -3.069  1.00  0.00           O  
HETATM   20  C10 UNL     1       0.017   0.958  -1.036  1.00  0.00           C  
HETATM   21  O8  UNL     1      -0.690   1.729  -1.927  1.00  0.00           O  
HETATM   22  C11 UNL     1      -2.595   0.467   0.109  1.00  0.00           C  
HETATM   23  H1  UNL     1      -6.647   0.879   1.693  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.679   1.856   2.844  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.684  -0.834   2.420  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.038  -2.614   2.256  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.099  -2.403   0.700  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.813  -0.790  -1.908  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.757  -1.522  -1.962  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.879  -0.068   0.500  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.220  -1.727  -0.048  1.00  0.00           H  
HETATM   32  H10 UNL     1       6.014   1.926  -0.893  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.876  -2.332  -0.144  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.126   1.362  -1.490  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.793  -0.431  -3.311  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.180   1.435  -0.058  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.588   2.675  -1.658  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.489   1.342  -0.487  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3    3    4
CONECT    4    5    5   22
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9   22   22
CONECT    9   10   20   28
CONECT   10   11
CONECT   11   12   18   29
CONECT   12   13   30   31
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   16   32
CONECT   17   33
CONECT   18   19   20   34
CONECT   19   35
CONECT   20   21   36
CONECT   21   37
CONECT   22   38
END

HMDB0000229
     RDKit          3D
Nicotinamide ribotide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -5.7549    1.3793    1.9028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6572    1.4678    1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124    2.4829    0.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6768    0.3820    0.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8428   -0.7400    1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8935   -1.7364    1.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278   -1.6014    0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.5044    0.0006 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.5431   -0.4392   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5665   -1.1241   -0.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6267   -0.7436   -1.1606 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9363   -0.7035   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -0.3065   -1.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426   -0.2260   -0.5512 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.3310    0.0251    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    1.0566   -1.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2595   -1.6798   -0.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515    0.6154   -1.7121 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0777    0.4861   -3.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171    0.9583   -1.0356 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6899    1.7290   -1.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    0.4668    0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6466    0.8792    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6793    1.8556    2.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6844   -0.8339    2.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381   -2.6137    2.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0988   -2.4033    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133   -0.7901   -1.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -1.5220   -1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790   -0.0677    0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -1.7265   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140    1.9263   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -2.3324   -0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1263    1.3624   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932   -0.4305   -3.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804    1.4351   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    2.6748   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4887    1.3423   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  6
 19 35  1  0
 20 36  1  1
 21 37  1  0
 22 38  1  0
M  CHG  1   8   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
b-Nicotinamide D-ribonucleotide	Generator
β-Nicotinamide D-ribonucleotide	Generator
Mononucleotide, nicotinamide	MeSH
Nicotinamide mononucleotide	MeSH
3-(Aminocarbonyl)-1-(5-O-phosphono-beta-D-ribofuranosyl)pyridinium	HMDB
3-(Aminocarbonyl)-1-(5-O-phosphono-β-D-ribofuranosyl)pyridinium	HMDB
NMN	HMDB
Nicotinamide ribonucleoside 5'-phosphate	HMDB
Nicotinamide ribonucleoside 5’-phosphate	HMDB
Nicotinamide ribonucleotide	HMDB
Nicotinamide ribotide	HMDB
beta-D-NMN	HMDB
beta-NMN	HMDB
beta-Nicotinamide D-ribonucleotide	HMDB
beta-Nicotinamide mononucleotide	HMDB
beta-Nicotinamide nucleotide	HMDB
beta-Nicotinamide ribonucleotide	HMDB
β-D-NMN	HMDB
β-NMN	HMDB
β-Nicotinamide mononucleotide	HMDB
β-Nicotinamide nucleotide	HMDB
β-Nicotinamide ribonucleotide	HMDB

Chemical Formula

C₁₁H₁₆N₂O₈P

Average Molecular Weight

335.2271

Monoisotopic Molecular Weight

335.06442701

IUPAC Name

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

Traditional Name

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

CAS Registry Number

75414-16-3

SMILES

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

InChI Identifier

InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/p+1/t7-,8-,9-,11-/m1/s1

InChI Key

DAYLJWODMCOQEW-TURQNECASA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nicotinamide nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyridine nucleotides

Sub Class

Nicotinamide nucleotides

Direct Parent

Nicotinamide nucleotides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nicotinamide mononucleotide (CHEBI:14648 )

Ontology

Physiological effect

Not Available

Disposition

Not Available

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

NAD Salvage (PathBank: SMP0000850)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	165.181	30932474
[M+H]+	Not Available	165.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000440

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.16 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-6.2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.21	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	163.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.71 m³·mol⁻¹	ChemAxon
Polarizability	29.05 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.03	30932474
DeepCCS	[M-H]-	159.634	30932474
DeepCCS	[M-2H]-	193.4	30932474
DeepCCS	[M+Na]+	168.454	30932474
AllCCS	[M+H]+	171.1	32859911
AllCCS	[M+H-H2O]+	168.1	32859911
AllCCS	[M+NH4]+	173.7	32859911
AllCCS	[M+Na]+	174.5	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.5	32859911
AllCCS	[M+HCOO]-	168.3	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nicotinamide ribotide,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	2928.0	Semi standard non polar	33892256
Nicotinamide ribotide,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	2826.1	Standard non polar	33892256
Nicotinamide ribotide,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	5052.7	Standard polar	33892256
Nicotinamide ribotide,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	2959.4	Semi standard non polar	33892256
Nicotinamide ribotide,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	2829.5	Standard non polar	33892256
Nicotinamide ribotide,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	5035.0	Standard polar	33892256
Nicotinamide ribotide,1TMS,isomer #3	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O	3047.9	Semi standard non polar	33892256
Nicotinamide ribotide,1TMS,isomer #3	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O	2811.1	Standard non polar	33892256
Nicotinamide ribotide,1TMS,isomer #3	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O	4741.4	Standard polar	33892256
Nicotinamide ribotide,1TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1	2971.8	Semi standard non polar	33892256
Nicotinamide ribotide,1TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1	2921.7	Standard non polar	33892256
Nicotinamide ribotide,1TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1	4919.4	Standard polar	33892256
Nicotinamide ribotide,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	2847.1	Semi standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	2869.6	Standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	4573.5	Standard polar	33892256
Nicotinamide ribotide,2TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	2990.1	Semi standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	2854.9	Standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	4238.4	Standard polar	33892256
Nicotinamide ribotide,2TMS,isomer #3	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2877.8	Semi standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #3	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2965.5	Standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #3	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	4336.5	Standard polar	33892256
Nicotinamide ribotide,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3003.9	Semi standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	2859.5	Standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	4237.9	Standard polar	33892256
Nicotinamide ribotide,2TMS,isomer #5	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	2905.0	Semi standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #5	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	2971.7	Standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #5	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	4322.6	Standard polar	33892256
Nicotinamide ribotide,2TMS,isomer #6	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C	3034.5	Semi standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #6	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C	2870.5	Standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #6	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C	4113.6	Standard polar	33892256
Nicotinamide ribotide,2TMS,isomer #7	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O)=C1	3011.2	Semi standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #7	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O)=C1	2926.2	Standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #7	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O)=C1	4044.3	Standard polar	33892256
Nicotinamide ribotide,2TMS,isomer #8	C[Si](C)(C)N(C(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1)[Si](C)(C)C	2954.0	Semi standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #8	C[Si](C)(C)N(C(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1)[Si](C)(C)C	2994.0	Standard non polar	33892256
Nicotinamide ribotide,2TMS,isomer #8	C[Si](C)(C)N(C(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1)[Si](C)(C)C	4505.0	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	2926.4	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	2875.2	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	3999.1	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #10	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O	2984.0	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #10	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O	2967.9	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #10	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O	3822.4	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2831.4	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2989.3	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	3962.2	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	2985.7	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	2899.6	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	3809.9	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2942.7	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2963.8	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	3704.5	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	2843.6	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	3031.4	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	4039.2	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3003.8	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	2903.7	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3819.0	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #7	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	2956.9	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #7	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	2970.9	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #7	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	3713.0	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #8	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	2866.4	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #8	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3037.6	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #8	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	4038.8	Standard polar	33892256
Nicotinamide ribotide,3TMS,isomer #9	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O)=C1	3015.7	Semi standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #9	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O)=C1	2983.9	Standard non polar	33892256
Nicotinamide ribotide,3TMS,isomer #9	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O)=C1	3547.7	Standard polar	33892256
Nicotinamide ribotide,4TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	2953.8	Semi standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	2891.6	Standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	3678.9	Standard polar	33892256
Nicotinamide ribotide,4TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2948.8	Semi standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2981.5	Standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	3478.7	Standard polar	33892256
Nicotinamide ribotide,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2819.6	Semi standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	3039.3	Standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	3706.2	Standard polar	33892256
Nicotinamide ribotide,4TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2995.5	Semi standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2987.4	Standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	3310.2	Standard polar	33892256
Nicotinamide ribotide,4TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	2950.8	Semi standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	2994.3	Standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	3524.8	Standard polar	33892256
Nicotinamide ribotide,4TMS,isomer #6	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	3002.4	Semi standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #6	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	3000.9	Standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #6	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	3340.2	Standard polar	33892256
Nicotinamide ribotide,4TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	2956.0	Semi standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3004.4	Standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3541.7	Standard polar	33892256
Nicotinamide ribotide,4TMS,isomer #8	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C	2999.0	Semi standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #8	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C	2996.3	Standard non polar	33892256
Nicotinamide ribotide,4TMS,isomer #8	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C	3415.2	Standard polar	33892256
Nicotinamide ribotide,5TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	3008.8	Semi standard non polar	33892256
Nicotinamide ribotide,5TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2980.1	Standard non polar	33892256
Nicotinamide ribotide,5TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	3158.9	Standard polar	33892256
Nicotinamide ribotide,5TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2944.4	Semi standard non polar	33892256
Nicotinamide ribotide,5TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2992.4	Standard non polar	33892256
Nicotinamide ribotide,5TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	3330.6	Standard polar	33892256
Nicotinamide ribotide,5TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	3002.7	Semi standard non polar	33892256
Nicotinamide ribotide,5TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	2984.4	Standard non polar	33892256
Nicotinamide ribotide,5TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	3193.9	Standard polar	33892256
Nicotinamide ribotide,5TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3002.7	Semi standard non polar	33892256
Nicotinamide ribotide,5TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3004.2	Standard non polar	33892256
Nicotinamide ribotide,5TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3228.5	Standard polar	33892256
Nicotinamide ribotide,6TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	3015.5	Semi standard non polar	33892256
Nicotinamide ribotide,6TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2975.7	Standard non polar	33892256
Nicotinamide ribotide,6TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	3086.2	Standard polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	3194.3	Semi standard non polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	3072.7	Standard non polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	5023.6	Standard polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3207.6	Semi standard non polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3072.7	Standard non polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	5016.2	Standard polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O	3294.6	Semi standard non polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O	3043.2	Standard non polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O	4764.9	Standard polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1	3259.6	Semi standard non polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1	3111.2	Standard non polar	33892256
Nicotinamide ribotide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1	4802.7	Standard polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3345.3	Semi standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3319.6	Standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	4605.2	Standard polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	3476.9	Semi standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	3291.0	Standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	4311.7	Standard polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3387.6	Semi standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3372.1	Standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	4343.7	Standard polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3473.4	Semi standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3294.9	Standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	4317.0	Standard polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3401.1	Semi standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3381.7	Standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	4339.6	Standard polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3517.4	Semi standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3269.6	Standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	4203.5	Standard polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)=C1	3508.3	Semi standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)=C1	3319.2	Standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)=C1	4128.6	Standard polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1)[Si](C)(C)C(C)(C)C	3420.7	Semi standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1)[Si](C)(C)C(C)(C)C	3385.0	Standard non polar	33892256
Nicotinamide ribotide,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)=C1)[Si](C)(C)C(C)(C)C	4400.2	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3621.5	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3471.5	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	4125.7	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O	3685.3	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O	3525.7	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O	3950.2	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3546.6	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3557.0	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	4073.9	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	3673.7	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	3458.1	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	3972.1	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3677.6	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3530.4	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3890.7	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O	3566.2	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O	3590.9	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O	4084.2	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3666.7	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3466.4	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	3988.4	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3675.7	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3545.2	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3904.2	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3571.8	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3603.2	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	4090.1	Standard polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)=C1	3725.0	Semi standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)=C1	3505.1	Standard non polar	33892256
Nicotinamide ribotide,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)=C1	3799.9	Standard polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3830.1	Semi standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3582.1	Standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3906.2	Standard polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3834.0	Semi standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3679.9	Standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3747.3	Standard polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3734.8	Semi standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3739.3	Standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3869.1	Standard polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3886.9	Semi standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3660.9	Standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3631.5	Standard polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O	3852.8	Semi standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O	3699.7	Standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O	3739.2	Standard polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3877.2	Semi standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3684.5	Standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3661.0	Standard polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3845.9	Semi standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3716.5	Standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3754.1	Standard polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3879.4	Semi standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3670.6	Standard non polar	33892256
Nicotinamide ribotide,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C	3679.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide ribotide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00tb-5902000000-fcee9746cbbfd4c7b910	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide ribotide GC-MS (3 TMS) - 70eV, Positive	splash10-000b-9321310000-a76824e42fa52329c65e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide ribotide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 10V, Positive-QTOF	splash10-000i-1009000000-5f50c20045d0b9493f33	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 20V, Positive-QTOF	splash10-004j-5219000000-3b516421e6f26f4266ee	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 40V, Positive-QTOF	splash10-0005-9500000000-4760ef36c1253b7200eb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 10V, Negative-QTOF	splash10-001i-2009000000-388bca4c5bcdaaf421c3	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 20V, Negative-QTOF	splash10-002b-9001000000-1dc8f508da2995c85814	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 40V, Negative-QTOF	splash10-004i-9000000000-b190037f5b434f05678b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 10V, Positive-QTOF	splash10-0079-0948000000-cda0f2a58f749153af62	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 20V, Positive-QTOF	splash10-00ei-5890000000-454378c4e02a99cc295a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide ribotide 40V, Positive-QTOF	splash10-0ac1-9500000000-606d177195e378bf9363	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Nucleus

Biospecimen Locations

Blood
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Nicotinate and nicotinamide metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	66.67 - 133.33 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	7618150	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Epithelial ovarian cancer	23163809	details
Urine	Detected and Quantified	133.33 - 600 umol/mmol creatinine	Adult (>18 years old)	Both	Sodium nitrate consumption	7618150	details

Associated Disorders and Diseases

Disease References

Sodium nitrate consumption
Jansen EH, van den Berg RH, Boink AB, Hegger C, Meulenbelt J: A new physiological biomarker for nitrate exposure in humans. Toxicol Lett. 1995 May;77(1-3):265-9. [PubMed:7618150 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

NICOTINAMIDE_NUCLEOTIDE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14181

PDB ID

Not Available

ChEBI ID

14648

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000111

Good Scents ID

Not Available

References

Synthesis Reference

Liu, Rihe; Visscher, Johannes. A novel preparation of nicotinamide mononucleotide. Nucleosides & Nucleotides (1994), 13(5), 1215-16.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Schuberth J: Volatile compounds detected in blood of drunk drivers by headspace/capillary gas chromatography/ion trap mass spectrometry. Biol Mass Spectrom. 1991 Nov;20(11):699-702. [PubMed:1799580 ]
Emanuelli M, Raffaelli N, Amici A, Balducci E, Natalini P, Ruggieri S, Magni G: The antitumor drug, 1,3-bis(2-chloroethyl)-1-nitroso-urea, inactivates human nicotinamide mononucleotide adenylyltransferase. Biochem Pharmacol. 1995 Feb 14;49(4):575-9. [PubMed:7872964 ]
Moriya F, Hashimoto Y: Postmortem production of ethanol and n-propanol in the brain of drowned persons. Am J Forensic Med Pathol. 2004 Jun;25(2):131-3. [PubMed:15166764 ]
Magni G, Amici A, Emanuelli M, Orsomando G, Raffaelli N, Ruggieri S: Structure and function of nicotinamide mononucleotide adenylyltransferase. Curr Med Chem. 2004 Apr;11(7):873-85. [PubMed:15078171 ]
Revollo JR, Korner A, Mills KF, Satoh A, Wang T, Garten A, Dasgupta B, Sasaki Y, Wolberger C, Townsend RR, Milbrandt J, Kiess W, Imai S: Nampt/PBEF/Visfatin regulates insulin secretion in beta cells as a systemic NAD biosynthetic enzyme. Cell Metab. 2007 Nov;6(5):363-75. [PubMed:17983582 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 5'-nucleotidase

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:: NT5E
Uniprot ID:: P21589
Molecular weight:: 57948.125

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

2. Cytosolic 5'-nucleotidase 1B

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:: NT5C1B
Uniprot ID:: Q96P26
Molecular weight:: 68803.055

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

3. Cytosolic 5'-nucleotidase 1A

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:: NT5C1A
Uniprot ID:: Q9BXI3
Molecular weight:: 41020.145

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

4. 5'(3')-deoxyribonucleotidase, cytosolic type

General function:: Involved in metal ion binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:: NT5C
Uniprot ID:: Q8TCD5
Molecular weight:: Not Available

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

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

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

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

6. Ectonucleotide pyrophosphatase/phosphodiesterase family member 1

General function:: Involved in catalytic activity
Specific function:: Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:: ENPP1
Uniprot ID:: P22413
Molecular weight:: 104923.58

Reactions

NAD + Water → Adenosine monophosphate + Nicotinamide ribotide	details

Enzyme Details

7. Ectonucleotide pyrophosphatase/phosphodiesterase family member 3

General function:: Involved in catalytic activity
Specific function:: Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:: ENPP3
Uniprot ID:: O14638
Molecular weight:: 100123.54

Reactions

NAD + Water → Adenosine monophosphate + Nicotinamide ribotide	details

Enzyme Details

8. Nicotinamide mononucleotide adenylyltransferase 1

General function:: Involved in nucleotidyltransferase activity
Specific function:: Catalyzes the formation of NAD(+) from nicotinamide mononucleotide (NMN) and ATP. Can also use the deamidated form; nicotinic acid mononucleotide (NaMN) as substrate with the same efficiency. Can use triazofurin monophosphate (TrMP) as substrate. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity, prefers NAD(+) and NAAD as substrates and degrades NADH, nicotinic acid adenine dinucleotide phosphate (NHD) and nicotinamide guanine dinucleotide (NGD) less effectively. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NAADP(+). Protects against axonal degeneration following mechanical or toxic insults.
Gene Name:: NMNAT1
Uniprot ID:: Q9HAN9
Molecular weight:: 31932.22

Reactions

Adenosine triphosphate + Nicotinamide ribotide → Pyrophosphate + NAD	details

Enzyme Details

9. Nicotinamide mononucleotide adenylyltransferase 3

General function:: Involved in nucleotidyltransferase activity
Specific function:: Catalyzes the formation of NAD(+) from nicotinamide mononucleotide (NMN) and ATP. Can also use the deamidated form; nicotinic acid mononucleotide (NaMN) as substrate with the same efficiency. Can use triazofurin monophosphate (TrMP) as substrate. Can also use GTP and ITP as nucleotide donors. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity, can use NAD (+), NADH, NAAD, nicotinic acid adenine dinucleotide phosphate (NHD), nicotinamide guanine dinucleotide (NGD) as substrates. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NAADP(+). Protects against axonal degeneration following injury.
Gene Name:: NMNAT3
Uniprot ID:: Q96T66
Molecular weight:: 18255.08

Reactions

Adenosine triphosphate + Nicotinamide ribotide → Pyrophosphate + NAD	details

Enzyme Details

10. Nicotinamide mononucleotide adenylyltransferase 2

General function:: Involved in nucleotidyltransferase activity
Specific function:: Catalyzes the formation of NAD(+) from nicotinamide mononucleotide (NMN) and ATP. Can also use the deamidated form; nicotinic acid mononucleotide (NaMN) as substrate but with a lower efficiency. Cannot use triazofurin monophosphate (TrMP) as substrate. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity prefers NAD(+), NADH and NAAD as substrates and degrades nicotinic acid adenine dinucleotide phosphate (NHD) less effectively. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NAADP(+).
Gene Name:: NMNAT2
Uniprot ID:: Q9BZQ4
Molecular weight:: 34438.38

Reactions

Adenosine triphosphate + Nicotinamide ribotide → Pyrophosphate + NAD	details

Only showing the first 10 proteins. There are 16 proteins in total.

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Showing metabocard for Nicotinamide ribotide (HMDB0000229)

MOL for HMDB0000229 (Nicotinamide ribotide)

3D MOL for HMDB0000229 (Nicotinamide ribotide)

3D SDF for HMDB0000229 (Nicotinamide ribotide)

3D-SDF for HMDB0000229 (Nicotinamide ribotide)

PDB for HMDB0000229 (Nicotinamide ribotide)

3D PDB for HMDB0000229 (Nicotinamide ribotide)

SMILES for HMDB0000229 (Nicotinamide ribotide)

INCHI for HMDB0000229 (Nicotinamide ribotide)

Structure for HMDB0000229 (Nicotinamide ribotide)

3D Structure for HMDB0000229 (Nicotinamide ribotide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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