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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10) Show 10 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-08-12 13:40:35 UTC

Update Date

2022-09-22 18:34:19 UTC

HMDB ID

HMDB0006809

Secondary Accession Numbers

HMDB06809

Metabolite Identification

Common Name

Nicotinic acid ribonucleoside

Description

Nicotinate D-ribonucleoside, also known as nicotinic acid riboside or beta-D-ribosylnicotinate, 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). Nicotinate D-ribonucleoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinate D-ribonucleoside exists in all living species, ranging from bacteria to humans. Within humans, nicotinate D-ribonucleoside participates in a number of enzymatic reactions. In particular, nicotinate D-ribonucleoside can be converted into nicotinic acid mononucleotide; which is catalyzed by the enzyme nicotinamide riboside kinase 1. In addition, nicotinate D-ribonucleoside can be biosynthesized from nicotinic acid mononucleotide; which is mediated by the enzyme cytosolic purine 5'-nucleotidase. A pyridine nucleoside consisting of nicotinic acid with a beta-D-ribofuranosyl moiety at the 1-position. In humans, nicotinate D-ribonucleoside is involved in nicotinate and nicotinamide metabolism.

Structure

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

HMDB0006809
     RDKit          3D
Nicotinic acid ribonucleoside
 32 33  0  0  0  0  0  0  0  0999 V2000
    2.7042    1.3920    2.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3952    0.8885    1.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    0.9408    1.6039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    0.2761    0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224   -0.2790   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888   -0.8568   -1.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -0.8687   -1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8027   -0.3239   -0.8381 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6514   -0.3307   -0.8867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0759    0.8783   -0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4115    0.6226   -0.0391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0215    1.7338    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236    2.9098    0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -0.6761    0.6998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5707   -1.3278    0.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430   -1.4165   -0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7989   -2.4155   -0.8087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3840    0.2515    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371    1.8598    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -0.2400   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -1.2904   -2.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0097   -1.3224   -2.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0172   -0.4239   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9562    0.4574   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    1.5022    0.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    1.8601    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9516    3.1011   -0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244   -0.5279    1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436   -2.1335    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799   -1.8150    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066   -3.1131   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    0.6870    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 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
  3 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  6
 11 24  1  6
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  1
 15 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  1  0
M  CHG  1   8   1
M  END


  Mrv1652307172022202D          

 18 19  0  0  0  0            999 V2000
10000.197910001.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.986010001.5454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4541 9999.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.169810000.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.544510000.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8301 9999.6947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.544510000.9308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.974710000.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2603 9999.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2603 9998.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9747 9998.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6892 9998.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6892 9999.6944    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10001.0744 9999.6119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.407010000.0969    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.661910000.8815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.486910000.8815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.741810000.0969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  9  5  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  0  0  0  0
 16  1  1  6  0  0  0
 15 13  1  1  0  0  0
 17  2  1  6  0  0  0
 18  3  1  1  0  0  0
M  CHG  1  13   1
M  END
> <DATABASE_ID>
HMDB0006809

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO6/c13-5-7-8(14)9(15)10(18-7)12-3-1-2-6(4-12)11(16)17/h1-4,7-10,13-15H,5H2/p+1/t7-,8-,9-,10-/m1/s1

> <INCHI_KEY>
PUEDDPCUCPRQNY-ZYUZMQFOSA-O

> <FORMULA>
C11H14NO6

> <MOLECULAR_WEIGHT>
256.232

> <EXACT_MASS>
256.082112185

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.20731172269263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.87

> <JCHEM_LOGP>
-5.313839270138412

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.72231566472464

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.757903592223079

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9841642628693164

> <JCHEM_POLAR_SURFACE_AREA>
111.10000000000002

> <JCHEM_REFRACTIVITY>
59.012299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.34e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006809
     RDKit          3D
Nicotinic acid ribonucleoside
 32 33  0  0  0  0  0  0  0  0999 V2000
    2.7042    1.3920    2.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3952    0.8885    1.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    0.9408    1.6039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    0.2761    0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224   -0.2790   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888   -0.8568   -1.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -0.8687   -1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8027   -0.3239   -0.8381 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6514   -0.3307   -0.8867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0759    0.8783   -0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4115    0.6226   -0.0391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0215    1.7338    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236    2.9098    0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -0.6761    0.6998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5707   -1.3278    0.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430   -1.4165   -0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7989   -2.4155   -0.8087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3840    0.2515    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371    1.8598    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -0.2400   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -1.2904   -2.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0097   -1.3224   -2.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0172   -0.4239   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9562    0.4574   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    1.5022    0.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    1.8601    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9516    3.1011   -0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244   -0.5279    1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436   -2.1335    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799   -1.8150    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066   -3.1131   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    0.6870    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 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
  3 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  6
 11 24  1  6
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  1
 15 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  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    8667.0368669.567   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8670.3748669.551   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8671.2488666.097   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8672.5848666.864   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8662.0838666.864   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8660.7508666.097   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8662.0838668.404   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8664.7538666.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.4198666.096   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.4198664.556   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.7538663.786   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.0878664.556   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8666.0878666.096   0.000  0.00  0.00           N+1
HETATM   14  O   UNK     0    8668.6728665.942   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8667.4268666.848   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.9028668.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.4428668.312   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.9188666.848   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3    4   18                                                       
CONECT    4    3                                                            
CONECT    5    6    7    9                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    9   13                                                       
CONECT    9    8   10    5                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   15                                                  
CONECT   14   15   18                                                       
CONECT   15   16   14   13                                                  
CONECT   16   15   17    1                                                  
CONECT   17   16   18    2                                                  
CONECT   18   17   14    3                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0006809
HETATM    1  O1  UNL     1       2.704   1.392   2.389  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.395   0.888   1.473  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.776   0.941   1.604  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.757   0.276   0.322  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.522  -0.279  -0.687  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.889  -0.857  -1.774  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.520  -0.869  -1.830  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.803  -0.324  -0.838  1.00  0.00           N1+
HETATM    9  C6  UNL     1      -0.651  -0.331  -0.887  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.076   0.878  -0.339  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.411   0.623  -0.039  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.022   1.734   0.787  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.924   2.910   0.026  1.00  0.00           O  
HETATM   14  C9  UNL     1      -2.345  -0.676   0.700  1.00  0.00           C  
HETATM   15  O5  UNL     1      -3.571  -1.328   0.587  1.00  0.00           O  
HETATM   16  C10 UNL     1      -1.243  -1.416  -0.020  1.00  0.00           C  
HETATM   17  O6  UNL     1      -1.799  -2.415  -0.809  1.00  0.00           O  
HETATM   18  C11 UNL     1       1.384   0.251   0.243  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.237   1.860   1.572  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.606  -0.240  -0.588  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.504  -1.290  -2.562  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.010  -1.322  -2.683  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.017  -0.424  -1.917  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.956   0.457  -0.979  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.086   1.502   0.939  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.470   1.860   1.723  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.952   3.101  -0.120  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.124  -0.528   1.759  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.644  -2.134   1.136  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.480  -1.815   0.694  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.107  -3.113  -0.916  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.771   0.687   1.034  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   19
CONECT    4    5    5   18
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8   22
CONECT    8    9   18   18
CONECT    9   10   16   23
CONECT   10   11
CONECT   11   12   14   24
CONECT   12   13   25   26
CONECT   13   27
CONECT   14   15   16   28
CONECT   15   29
CONECT   16   17   30
CONECT   17   31
CONECT   18   32
END

HMDB0006809
     RDKit          3D
Nicotinic acid ribonucleoside
 32 33  0  0  0  0  0  0  0  0999 V2000
    2.7042    1.3920    2.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3952    0.8885    1.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    0.9408    1.6039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    0.2761    0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224   -0.2790   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8888   -0.8568   -1.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -0.8687   -1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8027   -0.3239   -0.8381 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6514   -0.3307   -0.8867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0759    0.8783   -0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4115    0.6226   -0.0391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0215    1.7338    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236    2.9098    0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -0.6761    0.6998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5707   -1.3278    0.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2430   -1.4165   -0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7989   -2.4155   -0.8087 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3840    0.2515    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371    1.8598    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -0.2400   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -1.2904   -2.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0097   -1.3224   -2.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0172   -0.4239   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9562    0.4574   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    1.5022    0.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    1.8601    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9516    3.1011   -0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244   -0.5279    1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6436   -2.1335    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799   -1.8150    0.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066   -3.1131   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    0.6870    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 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
  3 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  6
 11 24  1  6
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  1
 15 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  1  0
M  CHG  1   8   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Nicotinic acid riboside	ChEBI
beta-D-Ribosylnicotinate	Kegg
Nicotinate riboside	Generator
b-D-Ribosylnicotinate	Generator
b-D-Ribosylnicotinic acid	Generator
beta-D-Ribosylnicotinic acid	Generator
Β-D-ribosylnicotinate	Generator
Β-D-ribosylnicotinic acid	Generator
Nicotinic acid D-ribonucleoside	Generator
D-Ribosylnicotinate	HMDB
Nicotinic acid ribose	HMDB
Ribosylnicotinate	HMDB
Nicotinate ribonucleoside	HMDB
Nicotinate ribose	HMDB
Nicotinic acid ribonucleoside	HMDB
3-Carboxy-1-beta-D-ribofuranosylpyridinium	HMDB
3-Carboxy-1-β-D-ribofuranosylpyridinium	HMDB
Nicotinic riboside	HMDB

Chemical Formula

C₁₁H₁₄NO₆

Average Molecular Weight

256.232

Monoisotopic Molecular Weight

256.082112185

IUPAC Name

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

Traditional Name

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

CAS Registry Number

4013-06-3

SMILES

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

InChI Identifier

InChI=1S/C11H13NO6/c13-5-7-8(14)9(15)10(18-7)12-3-1-2-6(4-12)11(16)17/h1-4,7-10,13-15H,5H2/p+1/t7-,8-,9-,10-/m1/s1

InChI Key

PUEDDPCUCPRQNY-ZYUZMQFOSA-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
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Monosaccharide
Pyridine
Pyridinium
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Alcohol
Primary alcohol
Organic nitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridine nucleoside (CHEBI:27748 )

Ontology

Not Available

Feces (PMID: 24628373)

Source

Endogenous

Endogenous (HMDB: HMDB0006809)

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

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nicotinate and Nicotinamide Metabolism (HMDB: HMDB0006809)
Nicotinate and Nicotinamide Metabolism (PathBank: SMP0121074)
NAD Metabolism (PathBank: SMP0002338)

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	5.34 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-5.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.76	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.01 m³·mol⁻¹	ChemAxon
Polarizability	24.21 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]+	158.685	31661259
DarkChem	[M-H]-	155.628	31661259
DeepCCS	[M+H]+	156.1	30932474
DeepCCS	[M-H]-	153.705	30932474
DeepCCS	[M-2H]-	187.548	30932474
DeepCCS	[M+Na]+	162.522	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.6	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.5	32859911
AllCCS	[M-H]-	156.3	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	155.7	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. Predicted by Afia on May 17, 2022.	1.53 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5046 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.54 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	156.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1038.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	214.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	72.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	262.2 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	281.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	225.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	620.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	53.7 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	932.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	401.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	198.6 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	206.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nicotinic acid ribonucleoside	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)[N+]1=CC=CC(=C1)C(O)=O	3596.1	Standard polar	33892256
Nicotinic acid ribonucleoside	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)[N+]1=CC=CC(=C1)C(O)=O	2120.8	Standard non polar	33892256
Nicotinic acid ribonucleoside	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)[N+]1=CC=CC(=C1)C(O)=O	2343.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nicotinic acid ribonucleoside,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@H](O)[C@@H]1O	2435.3	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1[N+]1=CC=CC(C(=O)O)=C1	2439.4	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@@H]1O	2438.3	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,1TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=C1	2354.2	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O	2378.6	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2410.2	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2405.5	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@@H]1O[Si](C)(C)C	2399.9	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	2371.6	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TMS,isomer #6	C[Si](C)(C)OC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2370.7	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2402.6	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2397.8	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2390.1	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,3TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2385.2	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2414.9	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@H](O)[C@@H]1O	2686.1	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1[N+]1=CC=CC(C(=O)O)=C1	2674.6	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@@H]1O	2686.3	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=C1	2622.8	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O	2879.2	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2911.9	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2910.9	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	2893.9	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	2881.1	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	2898.5	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3107.8	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3103.4	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3115.7	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C[N+]([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)=C1	3101.0	Semi standard non polar	33892256
Nicotinic acid ribonucleoside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)O[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	3262.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinic acid ribonucleoside GC-MS (Non-derivatized) - 70eV, Positive	splash10-009f-9640000000-9ecd90015c00728b3b07	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinic acid ribonucleoside GC-MS (4 TMS) - 70eV, Positive	splash10-0fa9-9442740000-0573803f81575b22f5c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinic acid ribonucleoside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinic acid ribonucleoside 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 - Nicotinic acid ribonucleoside 10V, Positive-QTOF	splash10-0a4i-0090000000-384ec325284b36db888b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinic acid ribonucleoside 20V, Positive-QTOF	splash10-002b-2190000000-5ab972cf9d81893b8388	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinic acid ribonucleoside 40V, Positive-QTOF	splash10-0006-9510000000-8e2f234fa7933273a714	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinic acid ribonucleoside 10V, Negative-QTOF	splash10-0a4i-0190000000-c2d0a64c0eb3d4ae2bfa	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinic acid ribonucleoside 20V, Negative-QTOF	splash10-0a4i-0490000000-bb44dd196c6e9a647df7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinic acid ribonucleoside 40V, Negative-QTOF	splash10-0zgu-9600000000-d17b549da8f5e8b2dd2b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinic acid ribonucleoside 10V, Positive-QTOF	splash10-06e9-1950000000-ae12a3b253bcd6d48ccc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinic acid ribonucleoside 20V, Positive-QTOF	splash10-001i-9510000000-cb2cf76989881501793c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinic acid ribonucleoside 40V, Positive-QTOF	splash10-001i-9100000000-9d7edc1ec5f0c17e5711	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nicotinate and nicotinamide metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024094

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161234

PDB ID

Not Available

ChEBI ID

27748

Food Biomarker Ontology

Not Available

VMH ID

NICRNS

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

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

Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + 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

Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + 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

Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + 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

Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + 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

Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphate	details

Enzyme Details

6. Cytosolic 5'-nucleotidase 3

General function:: Involved in magnesium ion binding
Specific function:: Can act both as nucleotidase and as phosphotransferase.
Gene Name:: NT5C3
Uniprot ID:: Q9H0P0
Molecular weight:: 33914.91

Reactions

Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphate	details

Enzyme Details

7. Cytosolic purine 5'-nucleotidase

General function:: Involved in 5'-nucleotidase activity
Specific function:: May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:: NT5C2
Uniprot ID:: P49902
Molecular weight:: 64969.2

Reactions

Nicotinic acid mononucleotide + Water → Nicotinic acid ribonucleoside + Phosphate	details

Enzyme Details

8. Purine nucleoside phosphorylase

General function:: Involved in purine-nucleoside phosphorylase activity
Specific function:: The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:: PNP
Uniprot ID:: P00491
Molecular weight:: 32117.69

Reactions

Nicotinic acid ribonucleoside + Phosphate → Nicotinic acid + Ribose 1-phosphate + Hydrogen Ion	details

Enzyme Details

9. Nicotinamide riboside kinase 1

General function:: Involved in ATP binding
Specific function:: Catalyzes the phosphorylation of nicotinamide riboside (NR) and nicotinic acid riboside (NaR) to form nicotinamide mononucleotide (NMN) and nicotinic acid mononucleotide (NaMN). The enzyme also phosphorylates the antitumor drugs tiazofurin and 3-deazaguanosine.
Gene Name:: NMRK1
Uniprot ID:: Q9NWW6
Molecular weight:: 20152.76

Reactions

Adenosine triphosphate + Nicotinic acid ribonucleoside → ADP + nicotinate beta-D-ribonucleotide	details
Nicotinic acid mononucleotide + ADP → Nicotinic acid ribonucleoside + Adenosine triphosphate	details

Enzyme Details

10. Nicotinamide riboside kinase 2

General function:: Nucleotide transport and metabolism
Specific function:: Catalyzes the phosphorylation of nicotinamide riboside (NR) and nicotinic acid riboside (NaR) to form nicotinamide mononucleotide (NMN) and nicotinic acid mononucleotide (NaMN). Reduces laminin matrix deposition and cell adhesion to laminin, but not to fibronectin. Involved in the regulation of PXN at the protein level and of PXN tyrosine phosphorylation. May play a role in the regulation of terminal myogenesis.
Gene Name:: NMRK2
Uniprot ID:: Q9NPI5
Molecular weight:: 26045.335

Reactions

Adenosine triphosphate + Nicotinic acid ribonucleoside → ADP + nicotinate beta-D-ribonucleotide	details
Nicotinic acid mononucleotide + ADP → Nicotinic acid ribonucleoside + Adenosine triphosphate	details

Showing metabocard for Nicotinic acid ribonucleoside (HMDB0006809)

MOL for HMDB0006809 (Nicotinic acid ribonucleoside)

3D MOL for HMDB0006809 (Nicotinic acid ribonucleoside)

3D SDF for HMDB0006809 (Nicotinic acid ribonucleoside)

3D-SDF for HMDB0006809 (Nicotinic acid ribonucleoside)

PDB for HMDB0006809 (Nicotinic acid ribonucleoside)

3D PDB for HMDB0006809 (Nicotinic acid ribonucleoside)

SMILES for HMDB0006809 (Nicotinic acid ribonucleoside)

INCHI for HMDB0006809 (Nicotinic acid ribonucleoside)

Structure for HMDB0006809 (Nicotinic acid ribonucleoside)

3D Structure for HMDB0006809 (Nicotinic acid ribonucleoside)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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