MiMeDB: Showing metabocard for Nicotinamide riboside (MMDBc0000372)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:20 UTC

Update Date

2024-10-15 16:56:32 UTC

Metabolite ID

MMDBc0000372

Metabolite Identification

Common Name

Nicotinamide riboside

Description

Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Nicotinamide riboside was originally identified as a nutrient in milk. It is a useful compound for the elevation of NAD+ levels in humans. Nicotinamide riboside has recently been discovered to be an NAD(+) precursor that is converted into nicotinamide mononucleotide by specific nicotinamide riboside kinases, Nrk1 and Nrk2. It has been shown that exogenous nicotinamide riboside promotes Sir2-dependent repression of recombination, improves gene silencing, and extends the lifespan of certain animal models without calorie restriction (PMID: 17482543 ). Supplementation in mammalian cells and mouse tissues increases NAD(+) levels and activates SIRT1 and SIRT3, culminating in enhanced oxidative metabolism and protection against high-fat diet-induced metabolic abnormalities (PMID: 22682224 ). Recent data suggest that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD+ synthesis (PMID: 18429699 ). Nicotinamide riboside kinase has an essential role in the phosphorylation of nicotinamide riboside and the cancer drug tiazofurin (PMID: 15137942 ).

Structure

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

HMDB0000855
     RDKit          3D
Nicotinamide riboside
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.3008   -0.5595   -0.0748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507   -0.9690   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687   -2.1002   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.0501    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.1554    0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592    2.0265    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    1.6407    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    0.4474    0.5408 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7997    0.1162    0.4427 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5204    0.9145   -0.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687    0.2943   -0.4129 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6540    0.7735   -1.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    2.1347   -1.4028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400   -1.1841   -0.4392 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1814   -1.7577    0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.2644   -0.1306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7482   -2.2785    0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.3599    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6060    0.2862   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988   -1.0552    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.4419    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    2.9892    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    2.3556    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3311    0.1445    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    0.6163    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    0.2907   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    0.4575   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356    2.3433   -0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970   -1.6770   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -1.3881    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452   -1.3669   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -3.0975    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -1.3205   -0.2719 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
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  2  0
 18  4  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  1
 11 25  1  1
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  6
 15 30  1  0
 16 31  1  6
 17 32  1  0
 18 33  1  0
M  CHG  1   8   1
M  END


  Mrv1652309042000132D          

 18 19  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6674   -2.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -2.1349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -2.9195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4125   -2.9195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4521   -1.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -3.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -3.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -4.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  1  1  0  0  0  0
  4  3  2  0  0  0  0
  7  4  1  1  0  0  0
  4  5  1  0  0  0  0
  6  2  1  0  0  0  0
  5  6  2  0  0  0  0
  6 17  1  0  0  0  0
  7  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  6  0  0  0
 10 14  1  1  0  0  0
 10 11  1  0  0  0  0
 11 13  1  6  0  0  0
 14 15  1  0  0  0  0
 17 16  2  0  0  0  0
 17 18  1  0  0  0  0
M  CHG  1   4   1
M  END
> <DATABASE_ID>
MMDBc0000372

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1

> <INCHI_KEY>
JLEBZPBDRKPWTD-TURQNECASA-O

> <FORMULA>
C11H15N2O5

> <MOLECULAR_WEIGHT>
255.2472

> <EXACT_MASS>
255.0980966

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.829741468645594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.27

> <JCHEM_LOGP>
-6.120781883805078

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.990744651010578

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.390918005504384

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6264200820796249

> <JCHEM_POLAR_SURFACE_AREA>
116.89

> <JCHEM_REFRACTIVITY>
60.83450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000855
     RDKit          3D
Nicotinamide riboside
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.3008   -0.5595   -0.0748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507   -0.9690   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687   -2.1002   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.0501    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.1554    0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592    2.0265    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    1.6407    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    0.4474    0.5408 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7997    0.1162    0.4427 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5204    0.9145   -0.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687    0.2943   -0.4129 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6540    0.7735   -1.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    2.1347   -1.4028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400   -1.1841   -0.4392 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1814   -1.7577    0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.2644   -0.1306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7482   -2.2785    0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.3599    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6060    0.2862   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988   -1.0552    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.4419    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    2.9892    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    2.3556    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3311    0.1445    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    0.6163    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    0.2907   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    0.4575   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356    2.3433   -0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970   -1.6770   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -1.3881    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452   -1.3669   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -3.0975    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -1.3205   -0.2719 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
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  2  0
 18  4  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  1
 11 25  1  1
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  6
 15 30  1  0
 16 31  1  6
 17 32  1  0
 18 33  1  0
M  CHG  1   8   1
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+1
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.246  -3.985   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.246  -3.985   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -5.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.770  -5.450   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.711  -3.509   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.675  -6.696   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.675  -6.696   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.049  -8.103   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.001   0.770   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    4                                                       
CONECT    4    3    7    5                                                  
CONECT    5    4    6                                                       
CONECT    6    2    5   17                                                  
CONECT    7    4    9    8                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11   12                                                  
CONECT   10    8   14   11                                                  
CONECT   11    9   10   13                                                  
CONECT   12    9                                                            
CONECT   13   11                                                            
CONECT   14   10   15                                                       
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17    6   16   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0000855
HETATM    1  N1  UNL     1      -5.301  -0.559  -0.075  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.951  -0.969  -0.210  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.669  -2.100  -0.703  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.910  -0.050   0.236  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.245   1.155   0.761  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.259   2.026   1.184  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.922   1.641   1.060  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.583   0.447   0.541  1.00  0.00           N1+
HETATM    9  C6  UNL     1       0.800   0.116   0.443  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.520   0.915  -0.429  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.769   0.294  -0.413  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.654   0.774  -1.536  1.00  0.00           C  
HETATM   13  O3  UNL     1       3.837   2.135  -1.403  1.00  0.00           O  
HETATM   14  C9  UNL     1       2.540  -1.184  -0.439  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.181  -1.758   0.673  1.00  0.00           O  
HETATM   16  C10 UNL     1       1.039  -1.264  -0.131  1.00  0.00           C  
HETATM   17  O5  UNL     1       0.748  -2.278   0.747  1.00  0.00           O  
HETATM   18  C11 UNL     1      -1.567  -0.360   0.146  1.00  0.00           C  
HETATM   19  H1  UNL     1      -5.606   0.286  -0.592  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.999  -1.055   0.510  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.296   1.442   0.851  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.532   2.989   1.603  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.190   2.356   1.404  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.331   0.145   1.419  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.261   0.616   0.539  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.651   0.291  -1.377  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.303   0.458  -2.527  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.836   2.343  -0.443  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.797  -1.677  -1.378  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.109  -1.388   0.767  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.545  -1.367  -1.117  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.420  -3.098   0.345  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.311  -1.320  -0.272  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    7   22
CONECT    7    8   23
CONECT    8    9   18   18
CONECT    9   10   16   24
CONECT   10   11
CONECT   11   12   14   25
CONECT   12   13   26   27
CONECT   13   28
CONECT   14   15   16   29
CONECT   15   30
CONECT   16   17   31
CONECT   17   32
CONECT   18   33
END

HMDB0000855
     RDKit          3D
Nicotinamide riboside
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.3008   -0.5595   -0.0748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507   -0.9690   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687   -2.1002   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.0501    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.1554    0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592    2.0265    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    1.6407    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    0.4474    0.5408 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7997    0.1162    0.4427 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5204    0.9145   -0.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687    0.2943   -0.4129 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6540    0.7735   -1.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    2.1347   -1.4028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400   -1.1841   -0.4392 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1814   -1.7577    0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.2644   -0.1306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7482   -2.2785    0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.3599    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6060    0.2862   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988   -1.0552    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.4419    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    2.9892    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    2.3556    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3311    0.1445    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    0.6163    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    0.2907   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    0.4575   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356    2.3433   -0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970   -1.6770   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -1.3881    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452   -1.3669   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -3.0975    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -1.3205   -0.2719 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
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  2  0
 18  4  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  1
 11 25  1  1
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  6
 15 30  1  0
 16 31  1  6
 17 32  1  0
 18 33  1  0
M  CHG  1   8   1
M  END

Synonyms

Value	Source
1-(beta-D-Ribofuranosyl)nicotinamide	ChEBI
beta-Nicotinamide D-riboside	ChEBI
Nicotinamide ribonucleoside	ChEBI
Nicotinamide ribose	ChEBI
Nicotinamide-beta-riboside	ChEBI
N-Ribosylnicotinamide	Kegg
1-(b-D-Ribofuranosyl)nicotinamide	Generator
1-(Β-D-ribofuranosyl)nicotinamide	Generator
b-Nicotinamide D-riboside	Generator
Β-nicotinamide D-riboside	Generator
Nicotinamide-b-riboside	Generator
Nicotinamide-β-riboside	Generator
1-b-D-Ribosyl-3-pyridinecarboxamide	HMDB
1-beta-D-Ribosyl-3-pyridinecarboxamide	HMDB
1-beta-delta-Ribosyl-3-pyridinecarboxamide	HMDB
3-(Aminocarbonyl)-1-beta-D-ribofuranosyl-pyridinium	HMDB
3-(Aminocarbonyl)-1-beta-delta-ribofuranosyl-pyridinium	HMDB
Ribosylnicotinamide	HMDB
SRT-647	HMDB
SRT 647	HMDB

Molecular Formula

C₁₁H₁₅N₂O₅

Average Mass

255.2472

Monoisotopic Mass

255.0980966

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1

InChI Key

JLEBZPBDRKPWTD-TURQNECASA-O

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
Pentose monosaccharide
Nicotinamide
Pyridine carboxylic acid or derivatives
Monosaccharide
Pyridine
Pyridinium
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Carboxamide group
Primary carboxylic acid amide
Organoheterocyclic compound
Oxacycle
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-glycosylnicotinamide (CHEBI:15927 )
pyridine nucleoside (CHEBI:15927 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.45 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-6.1	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.39	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.83 m³·mol⁻¹	ChemAxon
Polarizability	24.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191677	5'-nucleotidase	Unknown	P21589	Homo sapiens
MMDBp0191680	Cytosolic 5'-nucleotidase 1B	Unknown	Q96P26	Homo sapiens
MMDBp0191681	Cytosolic 5'-nucleotidase 1A	Unknown	Q9BXI3	Homo sapiens
MMDBp0191682	5'(3')-deoxyribonucleotidase, cytosolic type	Unknown	Q8TCD5	Homo sapiens
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo sapiens
MMDBp0191809	Ribosyldihydronicotinamide dehydrogenase [quinone]	Unknown	P16083	Homo sapiens
MMDBp0193860	Cytosolic 5'-nucleotidase 3	Enzyme	Q9H0P0	Homo sapiens
MMDBp0193932	Cytosolic purine 5'-nucleotidase	Unknown	P49902	Homo sapiens
MMDBp0193933	Purine nucleoside phosphorylase	Enzyme	P00491	Homo sapiens
MMDBp0193958	Nicotinamide riboside kinase 1	Unknown	Q9NWW6	Homo sapiens
MMDBp0195629	Nicotinamide riboside kinase 2	Unknown	Q9NPI5	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018373	Nicotinamide riboside	NMN	Trifunctional NAD biosynthesis/regulator protein NadR	Synthesis	PathBank	31602464
MMDBr0019605	Nicotinamide riboside	Nicotinamide ribotide	Nicotinamide riboside kinase	Phosphorylation	PathBank	31602464
MMDBr0019609	Nicotinamide riboside	D-Ribose	Uridine nucleosidase	Hydrolysis of a nucleotide	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Verrucomicrobia	2	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	342	Human stool; Human ; Human feces; Human pleural fluid plaque; Pig ; Human urine; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Cattle ; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	127	Human ; Human feces; Human appendix biopsy; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	162	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	15	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	108	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	25	Human stool; Human ; Human feces; Human pleural fluid plaque; Pig ; Human urine; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Cattle ; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	8	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified				HMDB

External Links

HMDB ID

HMDB0000855

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022281

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Nicotinamide riboside

METLIN ID

5818

PubChem Compound

439924

PDB ID

Not Available

ChEBI ID

15927

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Schalk-Hihi C, Zhang YZ, Markham GD: The conformation of NADH bound to inosine 5'-monophosphate dehydrogenase determined by transferred nuclear Overhauser effect spectroscopy. Biochemistry. 1998 May 19;37(20):7608-16. doi: 10.1021/bi980214h. [PubMed:9585576 ]
Wall KA, Klis M, Kornet J, Coyle D, Ame JC, Jacobson MK, Slama JT: Inhibition of the intrinsic NAD+ glycohydrolase activity of CD38 by carbocyclic NAD analogues. Biochem J. 1998 Nov 1;335 ( Pt 3):631-6. doi: 10.1042/bj3350631. [PubMed:9794804 ]
Pankiewicz KW, Watanabe KA, Lesiak-Watanabe K, Goldstein BM, Jayaram HN: The chemistry of nicotinamide adenine dinucleotide (NAD) analogues containing C-nucleosides related to nicotinamide riboside. Curr Med Chem. 2002 Apr;9(7):733-41. doi: 10.2174/0929867024606920. [PubMed:11966436 ]
Magni G, Amici A, Emanuelli M, Orsomando G, Raffaelli N, Ruggieri S: Enzymology of NAD+ homeostasis in man. Cell Mol Life Sci. 2004 Jan;61(1):19-34. doi: 10.1007/s00018-003-3161-1. [PubMed:14704851 ]
Bieganowski P, Brenner C: Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD+ in fungi and humans. Cell. 2004 May 14;117(4):495-502. doi: 10.1016/s0092-8674(04)00416-7. [PubMed:15137942 ]
Belenky P, Racette FG, Bogan KL, McClure JM, Smith JS, Brenner C: Nicotinamide riboside promotes Sir2 silencing and extends lifespan via Nrk and Urh1/Pnp1/Meu1 pathways to NAD+. Cell. 2007 May 4;129(3):473-84. doi: 10.1016/j.cell.2007.03.024. [PubMed:17482543 ]
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 ]
Canto C, Houtkooper RH, Pirinen E, Youn DY, Oosterveer MH, Cen Y, Fernandez-Marcos PJ, Yamamoto H, Andreux PA, Cettour-Rose P, Gademann K, Rinsch C, Schoonjans K, Sauve AA, Auwerx J: The NAD(+) precursor nicotinamide riboside enhances oxidative metabolism and protects against high-fat diet-induced obesity. Cell Metab. 2012 Jun 6;15(6):838-47. doi: 10.1016/j.cmet.2012.04.022. [PubMed:22682224 ]
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 ]

Showing metabocard for Nicotinamide riboside (MMDBc0000372)

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