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Showing NP-Card for Nicotinuric acid (NP0000996)

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Record Information
Version2.0
Created at2006-05-22 15:12:46 UTC
Updated at2021-06-29 00:47:43 UTC
NP-MRD IDNP0000996
Secondary Accession NumbersNone
Natural Product Identification
Common NameNicotinuric acid
DescriptionNicotinuric acid is an acylglycine. Acylglycines are normally minor metabolites of fatty acids. However, the excretion of certain acylglycines is increased in several inborn errors of metabolism. In certain cases, the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acylglycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) Which is an enzyme that catalyzes the chemical reaction acyl-CoA + glycine <-> CoA + N-acylglycine. Nicotinuric acid is the major detoxification product of nicotinic acid. It may serve as a simple quantitative index of hepatic biotransformation of nicotinic acid (PMID: 3243933 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000996 (Nicotinuric acid)


  Mrv1652303262019362D          

 13 13  0  0  0  0            999 V2000
    2.5006    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
Download

3D MOL for NP0000996 (Nicotinuric acid)

HMDB0003269
     RDKit          3D
Nicotinuric acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    3.3661    1.3302    0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    0.4586   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139    0.2310   -0.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -0.3075   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337    0.0883   -0.1187 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535   -0.5313   -0.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -1.4426   -1.4413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852   -0.2031   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110   -0.8509   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6856   -0.5699   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8124    0.4113    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322    1.0736    1.3469 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807    0.7683    0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039    0.9678   -0.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287   -0.1518   -1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999   -1.4098   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101    0.8342    0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663   -1.6153   -1.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5813   -1.0578   -0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7878    0.6766    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    1.3002    1.2861 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 13 21  1  0
M  END
Download

3D SDF for NP0000996 (Nicotinuric acid)


  Mrv1652303262019362D          

 13 13  0  0  0  0            999 V2000
    2.5006    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CNC(=O)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8N2O3/c11-7(12)5-10-8(13)6-2-1-3-9-4-6/h1-4H,5H2,(H,10,13)(H,11,12)

> <INCHI_KEY>
ZBSGKPYXQINNGF-UHFFFAOYSA-N

> <FORMULA>
C8H8N2O3

> <MOLECULAR_WEIGHT>
180.1607

> <EXACT_MASS>
180.053492132

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.928535256595644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(pyridin-3-yl)formamido]acetic acid

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
-1.4619292061489206

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.920864763325042

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9431722902833104

> <JCHEM_PKA_STRONGEST_BASIC>
3.7257917456440506

> <JCHEM_POLAR_SURFACE_AREA>
79.28999999999999

> <JCHEM_REFRACTIVITY>
43.960800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nicotinuric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000996 (Nicotinuric acid)

HMDB0003269
     RDKit          3D
Nicotinuric acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    3.3661    1.3302    0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    0.4586   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9139    0.2310   -0.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061   -0.3075   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337    0.0883   -0.1187 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535   -0.5313   -0.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -1.4426   -1.4413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852   -0.2031   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110   -0.8509   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6856   -0.5699   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8124    0.4113    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322    1.0736    1.3469 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807    0.7683    0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039    0.9678   -0.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287   -0.1518   -1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999   -1.4098   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101    0.8342    0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663   -1.6153   -1.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5813   -1.0578   -0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7878    0.6766    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    1.3002    1.2861 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 13 21  1  0
M  END
Download

PDB for NP0000996 (Nicotinuric acid)

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  O   UNK     0       4.668   1.155   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.334  -1.155   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -0.667   2.695   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       0.667   0.385   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      -4.668   0.385   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.001   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.334   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.667   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.000   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.334   1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.668  -1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.000  -1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.334  -1.925   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    6    8                                                       
CONECT    5   10   11                                                       
CONECT    6    4    7                                                       
CONECT    7    1    2    6                                                  
CONECT    8    3    4    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    5    9                                                       
CONECT   11    5   13                                                       
CONECT   12    9   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0000996 (Nicotinuric acid)

COMPND    HMDB0003269
HETATM    1  O1  UNL     1       3.366   1.330   0.789  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.605   0.459  -0.077  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.914   0.231  -0.467  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.506  -0.307  -0.665  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.234   0.088  -0.119  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.054  -0.531  -0.556  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.148  -1.443  -1.441  1.00  0.00           O  
HETATM    8  C4  UNL     1      -1.285  -0.203  -0.066  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.411  -0.851  -0.537  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.686  -0.570  -0.101  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.812   0.411   0.855  1.00  0.00           C  
HETATM   12  N2  UNL     1      -2.732   1.074   1.347  1.00  0.00           N  
HETATM   13  C8  UNL     1      -1.481   0.768   0.890  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.604   0.968  -0.461  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.429  -0.152  -1.777  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.600  -1.410  -0.471  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.210   0.834   0.598  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.266  -1.615  -1.288  1.00  0.00           H  
HETATM   19  H6  UNL     1      -4.581  -1.058  -0.449  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.788   0.677   1.238  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.626   1.300   1.286  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6   17
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   12   20
CONECT   12   13   13
CONECT   13   21
END
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SMILES for NP0000996 (Nicotinuric acid)

OC(=O)CNC(=O)C1=CN=CC=C1
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INCHI for NP0000996 (Nicotinuric acid)

InChI=1S/C8H8N2O3/c11-7(12)5-10-8(13)6-2-1-3-9-4-6/h1-4H,5H2,(H,10,13)(H,11,12)
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View in JSmol
Synonyms
ValueSource
N-(Pyridin-3-ylcarbonyl)glycineChEBI
N-NicotinylglycineChEBI
NicotinoylglycineChEBI
NicotinurateChEBI
NicotinylglycineChEBI
NicotinateGenerator
Nicotinic acidGenerator
N-(3-Pyridinylcarbonyl)-(9ci)-glycineHMDB
N-(3-Pyridinylcarbonyl)-glycineHMDB
N-Nicotinoyl-(8ci)-glycineHMDB
N-Nicotinoyl-glycineHMDB
N-NicotinurateHMDB
N-Nicotinuric acidHMDB
Nicotinoyl-glycineHMDB
Nicotinuric acid, monosodium saltHMDB
Nicotinuric acidChEBI
Chemical FormulaC8H8N2O3
Average Mass180.1607 Da
Monoisotopic Mass180.05349 Da
IUPAC Name2-[(pyridin-3-yl)formamido]acetic acid
Traditional Namenicotinuric acid
CAS Registry Number583-08-4
SMILES
OC(=O)CNC(=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C8H8N2O3/c11-7(12)5-10-8(13)6-2-1-3-9-4-6/h1-4H,5H2,(H,10,13)(H,11,12)
InChI KeyZBSGKPYXQINNGF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
Lates calcariferLOTUS Database
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Nicotinamide
  • Pyridine
  • Heteroaromatic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.49 g/LALOGPS
logP-0.23ALOGPS
logP-1.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.94ChemAxon
pKa (Strongest Basic)3.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.96 m³·mol⁻¹ChemAxon
Polarizability16.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003269
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023135
KNApSAcK IDNot Available
Chemspider ID61774
KEGG Compound IDC05380
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNiacin
METLIN ID1499
PubChem Compound68499
PDB IDNot Available
ChEBI ID7563
Good Scents IDNot Available
References
General References
  1. Hengen N, Seiberth V, Hengen M: High-performance liquid-chromatographic determination of free nicotinic acid and its metabolite, nicotinuric acid, in plasma and urine. Clin Chem. 1978 Oct;24(10):1740-3. [PubMed:699281 ]
  2. Miyauchi Y, Sano N, Nakamura T: Simultaneous determination of nicotinic acid and its two metabolites in human plasma using solid-phase extraction in combination with high performance liquid chromatography. Int J Vitam Nutr Res. 1993;63(2):145-9. [PubMed:8407165 ]
  3. Neuvonen PJ, Roivas L, Laine K, Sundholm O: The bioavailability of sustained release nicotinic acid formulations. Br J Clin Pharmacol. 1991 Oct;32(4):473-6. [PubMed:1958442 ]
  4. Figge HL, Figge J, Souney PF, Sacks FM, Shargel L, Janosik JE, Kaul AF: Comparison of excretion of nicotinuric acid after ingestion of two controlled release nicotinic acid preparations in man. J Clin Pharmacol. 1988 Dec;28(12):1136-40. [PubMed:3243933 ]
  5. Pfuhl P, Karcher U, Haring N, Baumeister A, Tawab MA, Schubert-Zsilavecz M: Simultaneous determination of niacin, niacinamide and nicotinuric acid in human plasma. J Pharm Biomed Anal. 2005 Jan 4;36(5):1045-52. [PubMed:15620531 ]