MiMeDB: Showing metabocard for Nicotinic acid ribonucleoside (MMDBc0000617)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:13 UTC

Update Date

2022-08-31 06:10:24 UTC

Metabolite ID

MMDBc0000617

Metabolite Identification

Common Name

Nicotinic acid ribonucleoside

Description

Nicotinic acid ribonucleoside (CAS: 17720-18-2) 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). Nicotinic acid ribonucleoside is involved in the nicotinate and nicotinamide metabolism pathways. Nicotinic acid ribonucleoside can be reversibly converted into nicotinate and nicotinate D-ribonucleoside by purine-nucleoside phosphorylase (EC 2.4.2.1) and 5'-nucleotidase (EC 3.1.3.5), respectively.

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>
MMDBc0000617

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₁H₁₄NO₆

Average Mass

256.232

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-009f-9640000000-9ecd90015c00728b3b07	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0fa9-9442740000-0573803f81575b22f5c8	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-c2d0a64c0eb3d4ae2bfa	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0490000000-bb44dd196c6e9a647df7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zgu-9600000000-d17b549da8f5e8b2dd2b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-384ec325284b36db888b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-2190000000-5ab972cf9d81893b8388	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9510000000-8e2f234fa7933273a714	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06e9-1950000000-ae12a3b253bcd6d48ccc	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9510000000-cb2cf76989881501793c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-9d7edc1ec5f0c17e5711	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191677	5'-nucleotidase	Unknown	P21589	Homo sapiens
MMDBp0191680	Cytosolic 5'-nucleotidase 1B	Unknown	Q96P26	Homo sapiens
MMDBp0191681	Cytosolic 5'-nucleotidase 1A	Unknown	Q9BXI3	Homo sapiens
MMDBp0191682	5'(3')-deoxyribonucleotidase, cytosolic type	Unknown	Q8TCD5	Homo sapiens
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo sapiens
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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001756	Adenosine triphosphate	ADP	Not Available	Nicotinate D-Ribonucleoside Kinase	VMH	30371894
MMDBr0001773	Hydrogen Ion	Nicotinic acid ribonucleoside	Not Available	Nucleotide Phosphatase	VMH	30371894
MMDBr0007509	Hydrogen Ion	Nicotinic acid ribonucleoside	Not Available	Nucleotide phosphatase	VMH	30371894
MMDBr0007921	Water	Nicotinic acid ribonucleoside	Not Available	Nicotinate D-Ribonucleotide Phosphohydrolase	VMH	30371894
MMDBr0019611	Nicotinic acid ribonucleoside	Hydrogen Ion	Nicotinamide riboside kinase	Phosphorylation	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	Firmicutes	354	Human ; Human feces; Human stool; 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	152	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	Metabolic reconstruction
Bacteria	Actinobacteria	103	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Feces	Detected but not Quantified	Infant (0-1 year old)	NULL	Normal	HMDB	24628373
Human Feces	Detected but not Quantified	Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
Human Feces	Detected but not Quantified	Infant (0-1 year old)	Not Specified	Normal	HMDB	24628373
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	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0006809

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

References

Synthesis Reference

Not Available

General References

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

Showing metabocard for Nicotinic acid ribonucleoside (MMDBc0000617)

MOL for #<Metabolite:0x00007f5a9cb1b6d0>

3D MOL for #<Metabolite:0x00007f5a9cb1b6d0>

3D SDF for #<Metabolite:0x00007f5a9cb1b6d0>

3D-SDF for #<Metabolite:0x00007f5a9cb1b6d0>

PDB for #<Metabolite:0x00007f5a9cb1b6d0>

3D PDB for #<Metabolite:0x00007f5a9cb1b6d0>

SMILES for #<Metabolite:0x00007f5a9cb1b6d0>

INCHI for #<Metabolite:0x00007f5a9cb1b6d0>

Structure for #<Metabolite:0x00007f5a9cb1b6d0>

3D Structure for #<Metabolite:0x00007f5a9cb1b6d0>