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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-02-03 09:22:11 UTC

Update Date

2022-09-22 18:35:07 UTC

HMDB ID

HMDB0011648

Secondary Accession Numbers

HMDB11648

Metabolite Identification

Common Name

1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide

Description

1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide is the reduced form of nicotinamide riboside. Nicotinamide riboside or NR is a natural product found in milk. It can exist in both the oxidized and reduced form. Nicotinamide riboside is a newly discovered precursor to NAD ( nicotinamide adenine dinucleotide). Nicotinamide riboside kinases (Nrks) are essential for this NAD synthesis pathway. Nrks actually constitute a distinct pathway of NAD biosynthesis and it appears that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD synthesis (PMID: 18429699 ). NAD homeostasis is related to the free radical-mediated production of reactive oxygen species responsible for irreversible cellular damage in infectious disease, diabetes, inflammatory syndromes, neurodegeneration and cancer. (PMID: 18508649 ). Baseline requirements for NAD synthesis can be met either with dietary tryptophan or with less than 20 mg of daily niacin, which consists of nicotinic acid and/or nicotinamide. Reduced nicotinamide riboside is also known to be a substrate for ribosyldihydronicotinamide dehydrogenase (EC 1.10.99.2). It is also a substrate for purine-nucleoside phosphorylase (PNP) - (PMID: 9030766 ).

Structure

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

HMDB0011648
     RDKit          3D
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.9934   -0.1672    2.1520 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185   -0.3871    2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0270   -0.8712    3.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.0924    0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -0.3259    0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175   -0.0674   -0.3067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709   -0.3564   -0.2275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3895    0.0056   -1.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767   -0.3670   -0.9769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7207    0.1238   -1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9912   -0.2653   -1.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8464    0.2506    0.3957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4746   -0.6147    1.2804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004    0.3951    0.8539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1844   -0.2489    2.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624    0.4717   -1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6519    0.7149   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516    0.4668   -0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4073    0.1232    3.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6107   -0.2890    1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -0.7416    1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8873   -1.4472   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720   -1.4718   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4791   -0.2721   -2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6743    1.2210   -1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3630   -0.8887   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3605    1.2363    0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3857   -0.8734    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    1.4606    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929    0.4060    2.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    0.6678   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    1.1337   -2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067   -0.3178   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188    1.3879   -0.0645 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18  4  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  7 22  1  1
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 14 29  1  1
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
M  END


  Mrv0541 02241201492D          

 18 19  0  0  1  0            999 V2000
   12.2596   -5.7652    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0226   -4.6434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5911   -5.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0065   -6.5507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7440   -4.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3124   -4.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9302   -5.7652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1795   -6.5507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4900   -7.2155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7440   -3.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3124   -3.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1521   -5.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6960   -7.2118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0226   -2.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4540   -2.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9821   -4.7039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1679   -3.3894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4691   -2.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  2  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  1  0  0  0
  8 13  1  6  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
  7  8  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011648

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1,3-4,7-9,11,14-16H,2,5H2,(H2,12,17)/t7-,8-,9-,11-/m1/s1

> <INCHI_KEY>
MAKBMGXNXXXBFE-TURQNECASA-N

> <FORMULA>
C11H16N2O5

> <MOLECULAR_WEIGHT>
256.2551

> <EXACT_MASS>
256.105921632

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
24.924657413187198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydropyridine-3-carboxamide

> <ALOGPS_LOGP>
-1.94

> <JCHEM_LOGP>
-2.091022263

> <ALOGPS_LOGS>
-0.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.93250853693095

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.558402582027185

> <JCHEM_PKA_STRONGEST_BASIC>
3.8875677369836095

> <JCHEM_POLAR_SURFACE_AREA>
116.25

> <JCHEM_REFRACTIVITY>
61.837300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
reduced nicotinamide riboside

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011648
     RDKit          3D
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.9934   -0.1672    2.1520 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185   -0.3871    2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0270   -0.8712    3.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.0924    0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -0.3259    0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175   -0.0674   -0.3067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709   -0.3564   -0.2275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3895    0.0056   -1.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767   -0.3670   -0.9769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7207    0.1238   -1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9912   -0.2653   -1.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8464    0.2506    0.3957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4746   -0.6147    1.2804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004    0.3951    0.8539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1844   -0.2489    2.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624    0.4717   -1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6519    0.7149   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516    0.4668   -0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4073    0.1232    3.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6107   -0.2890    1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -0.7416    1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8873   -1.4472   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720   -1.4718   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4791   -0.2721   -2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6743    1.2210   -1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3630   -0.8887   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3605    1.2363    0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3857   -0.8734    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    1.4606    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929    0.4060    2.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    0.6678   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    1.1337   -2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067   -0.3178   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188    1.3879   -0.0645 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18  4  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  7 22  1  1
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 14 29  1  1
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      22.885 -10.762   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      24.309  -8.668   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0      21.637  -9.866   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      22.412 -12.228   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.655  -7.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.983  -7.885   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.403 -10.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.868 -12.228   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      23.315 -13.469   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      25.655  -6.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.983  -6.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.951 -10.282   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      19.966 -13.462   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      24.309  -5.565   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.981  -5.559   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.633  -8.781   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      28.313  -6.327   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      27.009  -3.951   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12    8                                                  
CONECT    8    4   13    7                                                  
CONECT    9    4                                                            
CONECT   10    5   14   15                                                  
CONECT   11    6   14                                                       
CONECT   12    7   16                                                       
CONECT   13    8                                                            
CONECT   14   10   11                                                       
CONECT   15   10   17   18                                                  
CONECT   16   12                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0011648
HETATM    1  N1  UNL     1       4.993  -0.167   2.152  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.618  -0.387   2.049  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.027  -0.871   3.069  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.834  -0.092   0.844  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.543  -0.326   0.821  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.718  -0.067  -0.307  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.671  -0.356  -0.228  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.390   0.006  -1.363  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.677  -0.367  -0.977  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.721   0.124  -1.949  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.991  -0.265  -1.534  1.00  0.00           O  
HETATM   12  C7  UNL     1      -2.846   0.251   0.396  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.475  -0.615   1.280  1.00  0.00           O  
HETATM   14  C8  UNL     1      -1.400   0.395   0.854  1.00  0.00           C  
HETATM   15  O5  UNL     1      -1.184  -0.249   2.065  1.00  0.00           O  
HETATM   16  C9  UNL     1       1.362   0.472  -1.449  1.00  0.00           C  
HETATM   17  C10 UNL     1       2.652   0.715  -1.454  1.00  0.00           C  
HETATM   18  C11 UNL     1       3.552   0.467  -0.316  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.407   0.123   3.058  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.611  -0.289   1.337  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.102  -0.742   1.731  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.887  -1.447  -0.062  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.672  -1.472  -0.888  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.479  -0.272  -2.950  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.674   1.221  -1.994  1.00  0.00           H  
HETATM   26  H8  UNL     1      -5.363  -0.889  -2.236  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.361   1.236   0.336  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.386  -0.873   0.994  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.178   1.461   0.896  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.293   0.406   2.806  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.724   0.668  -2.311  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.080   1.134  -2.379  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.307  -0.318  -0.610  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.119   1.388  -0.065  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3    4
CONECT    4    5    5   18
CONECT    5    6   21
CONECT    6    7   16
CONECT    7    8   14   22
CONECT    8    9
CONECT    9   10   12   23
CONECT   10   11   24   25
CONECT   11   26
CONECT   12   13   14   27
CONECT   13   28
CONECT   14   15   29
CONECT   15   30
CONECT   16   17   17   31
CONECT   17   18   32
CONECT   18   33   34
END

HMDB0011648
     RDKit          3D
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.9934   -0.1672    2.1520 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185   -0.3871    2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0270   -0.8712    3.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.0924    0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -0.3259    0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175   -0.0674   -0.3067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709   -0.3564   -0.2275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3895    0.0056   -1.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767   -0.3670   -0.9769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7207    0.1238   -1.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9912   -0.2653   -1.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8464    0.2506    0.3957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4746   -0.6147    1.2804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004    0.3951    0.8539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1844   -0.2489    2.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624    0.4717   -1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6519    0.7149   -1.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516    0.4668   -0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4073    0.1232    3.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6107   -0.2890    1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -0.7416    1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8873   -1.4472   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720   -1.4718   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4791   -0.2721   -2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6743    1.2210   -1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3630   -0.8887   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3605    1.2363    0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3857   -0.8734    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    1.4606    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929    0.4060    2.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    0.6678   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796    1.1337   -2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067   -0.3178   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188    1.3879   -0.0645 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18  4  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  7 22  1  1
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 14 29  1  1
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Reduced nicotinamide riboside	ChEBI
1-(b-D-Ribofuranosyl)-1,4-dihydronicotinamide	Generator
1-(Β-D-ribofuranosyl)-1,4-dihydronicotinamide	Generator

Chemical Formula

C₁₁H₁₆N₂O₅

Average Molecular Weight

256.2551

Monoisotopic Molecular Weight

256.105921632

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,4-dihydropyridine-3-carboxamide

Traditional Name

reduced nicotinamide riboside

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C11H16N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1,3-4,7-9,11,14-16H,2,5H2,(H2,12,17)/t7-,8-,9-,11-/m1/s1

InChI Key

MAKBMGXNXXXBFE-TURQNECASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
N-substituted nicotinamide
Pentose monosaccharide
Dihydropyridine
Hydropyridine
Monosaccharide
Vinylogous amide
Tetrahydrofuran
Carboxamide group
Secondary alcohol
Primary carboxylic acid amide
Carboxylic acid derivative
Enamine
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Alcohol
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dihydropyridine (CHEBI:55458 )
pyridine nucleoside (CHEBI:55458 )

Ontology

Not Available

Endogenous (HMDB: HMDB0011648)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	80.5 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.1	ChemAxon
logS	-0.5	ALOGPS
pKa (Strongest Acidic)	12.56	ChemAxon
pKa (Strongest Basic)	3.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.84 m³·mol⁻¹	ChemAxon
Polarizability	24.92 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
DarkChem	[M+H]+	158.141	31661259
DarkChem	[M-H]-	155.843	31661259
DeepCCS	[M+H]+	155.81	30932474
DeepCCS	[M-H]-	153.414	30932474
DeepCCS	[M-2H]-	187.606	30932474
DeepCCS	[M+Na]+	163.021	30932474
AllCCS	[M+H]+	159.0	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	162.3	32859911
AllCCS	[M+Na]+	163.3	32859911
AllCCS	[M-H]-	157.4	32859911
AllCCS	[M+Na-2H]-	157.3	32859911
AllCCS	[M+HCOO]-	157.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	1.79 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4484 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.08 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	160.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1101.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	236.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	68.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	250.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	261.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	551.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	633.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	94.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1064.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	542.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	346.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	292.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide	NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	4004.8	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide	NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2093.9	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide	NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2606.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(N)=O)=C2)[C@H](O)[C@@H]1O	2530.4	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(N)=O)=C2)[C@@H]1O	2550.7	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=CCC(C(N)=O)=C1	2542.8	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,1TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=CC1	2592.8	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(N)=O)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2539.6	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(N)=O)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2528.2	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TMS,isomer #3	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)C=CC1	2579.0	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	2541.8	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TMS,isomer #5	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C=CC1	2575.4	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TMS,isomer #6	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C=CC1	2574.2	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TMS,isomer #7	C[Si](C)(C)N(C(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=CC1)[Si](C)(C)C	2651.5	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(N)=O)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2516.2	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=CC1	2587.4	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TMS,isomer #3	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=CC1	2569.4	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O	2693.6	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TMS,isomer #5	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=CC1	2571.7	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	2682.5	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	2692.4	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=CC1	2576.3	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=CC1	2514.5	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=CC1	3217.1	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2710.9	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2632.6	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	3147.6	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2691.2	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2607.2	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	3095.0	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2686.6	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2618.8	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	3094.3	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2694.3	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2667.1	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2979.1	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(N)=O)=C2)[C@H](O)[C@@H]1O	2769.5	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(N)=O)=C2)[C@@H]1O	2785.2	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=CCC(C(N)=O)=C1	2768.1	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=CC1	2835.4	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(N)=O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2971.1	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(N)=O)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2951.9	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=CC1	3042.7	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	2962.2	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=CC1	3026.6	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=CC1	3018.4	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=CC1)[Si](C)(C)C(C)(C)C	3015.8	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(N)=O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3167.8	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=CC1	3227.3	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=CC1	3220.3	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O	3250.6	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=CC1	3203.6	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O	3234.6	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3232.9	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[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)C=CC1	3391.7	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[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)C=CC1	3345.3	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([C@@H]2O[C@H](CO[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)C=CC1	3477.2	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3415.9	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3439.9	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3417.2	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3405.5	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3418.7	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3373.4	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(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	3403.0	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(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	3429.0	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CCC(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	3368.6	Standard polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3589.2	Semi standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3607.4	Standard non polar	33892256
1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CCC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3315.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-9530000000-4d6ac885182221a2aa89	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-6859800000-1a270761d5d36bc8a099	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 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 - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 10V, Positive-QTOF	splash10-0a4l-0190000000-bdc634b8a50f94b7870a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 20V, Positive-QTOF	splash10-0a4i-6890000000-ab6e26f5e654c6811266	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 40V, Positive-QTOF	splash10-056r-6900000000-5629c3568948565f5b4e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 10V, Negative-QTOF	splash10-0a4i-1290000000-49126d2627802aa8069d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 20V, Negative-QTOF	splash10-00dr-2930000000-2f9086897c3a523ff340	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 40V, Negative-QTOF	splash10-0006-9200000000-d2c4dffcef36a3083d75	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 10V, Negative-QTOF	splash10-0a4i-0090000000-51f92fb4ea398fb5eb47	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 20V, Negative-QTOF	splash10-0ac0-7910000000-75b65c4ba937a2b996e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 40V, Negative-QTOF	splash10-0006-9400000000-f87d7c7a1d4c264a9b1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 10V, Positive-QTOF	splash10-057i-1910000000-be783114ea0197565e8a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 20V, Positive-QTOF	splash10-0a7i-5970000000-d3c1ca153f39f41e5d41	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide 40V, Positive-QTOF	splash10-0a59-9500000000-5a95eff6714627a2985b	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028341

KNApSAcK ID

Not Available

Chemspider ID

9681931

KEGG Compound ID

C15497

BioCyc ID

CPD-7229

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11507134

PDB ID

Not Available

ChEBI ID

55458

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bogan KL, Brenner C: Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition. Annu Rev Nutr. 2008;28:115-30. doi: 10.1146/annurev.nutr.28.061807.155443. [PubMed:18429699 ]
Magni G, Orsomando G, Raffelli N, Ruggieri S: Enzymology of mammalian NAD metabolism in health and disease. Front Biosci. 2008 May 1;13:6135-54. [PubMed:18508649 ]
Wielgus-Kutrowska B, Kulikowska E, Wierzchowski J, Bzowska A, Shugar D: Nicotinamide riboside, an unusual, non-typical, substrate of purified purine-nucleoside phosphorylases. Eur J Biochem. 1997 Jan 15;243(1-2):408-14. [PubMed:9030766 ]

Enzymes

Enzyme Details

1. Ribosyldihydronicotinamide dehydrogenase [quinone]

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO2
Uniprot ID:: P16083
Molecular weight:: 25918.4

Reactions

1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide + a quinone → 1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone	details

Showing metabocard for 1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide (HMDB0011648)

MOL for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

3D MOL for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

3D SDF for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

3D-SDF for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

PDB for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

3D PDB for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

SMILES for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

INCHI for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

Structure for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

3D Structure for HMDB0011648 (1-(beta-D-Ribofuranosyl)-1,4-dihydronicotinamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions