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Showing metabocard for Nicotinuric acid (HMDB0003269)

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enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:46 UTC
Update Date2023-02-21 17:16:34 UTC
HMDB IDHMDB0003269
Secondary Accession Numbers
  • HMDB03269
Metabolite 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
Data?1676999794
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003269 (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
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3D MOL for HMDB0003269 (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 HMDB0003269 (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>
HMDB0003269

> <DATABASE_NAME>
hmdb

> <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 HMDB0003269 (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
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PDB for HMDB0003269 (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 HMDB0003269 (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 HMDB0003269 (Nicotinuric acid)

OC(=O)CNC(=O)C1=CN=CC=C1
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INCHI for HMDB0003269 (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 JSmolView NMR AssignmentsView Stereo Labels
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 Molecular Weight180.1607
Monoisotopic Molecular Weight180.053492132
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg138.07530932474
[M+H]+MetCCS_train_pos143.60830932474
[M-H]-Not Available138.075http://allccs.zhulab.cn/database/detail?ID=AllCCS00000055
[M+H]+Not Available144.146http://allccs.zhulab.cn/database/detail?ID=AllCCS00000055
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.5931661259
DarkChem[M-H]-133.6431661259
DeepCCS[M+H]+136.79230932474
DeepCCS[M-H]-134.30530932474
DeepCCS[M-2H]-170.01530932474
DeepCCS[M+Na]+144.67330932474
AllCCS[M+H]+138.432859911
AllCCS[M+H-H2O]+134.232859911
AllCCS[M+NH4]+142.332859911
AllCCS[M+Na]+143.532859911
AllCCS[M-H]-137.032859911
AllCCS[M+Na-2H]-137.832859911
AllCCS[M+HCOO]-138.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.2.22 minutes32390414
Predicted by Siyang on May 30, 20229.2158 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.48 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid187.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid788.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid288.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid62.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid162.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid43.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid252.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid277.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)351.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid578.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid38.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid916.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid181.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid189.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate602.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA258.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water244.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Nicotinuric acidOC(=O)CNC(=O)C1=CN=CC=C12702.3Standard polar33892256
Nicotinuric acidOC(=O)CNC(=O)C1=CN=CC=C11725.6Standard non polar33892256
Nicotinuric acidOC(=O)CNC(=O)C1=CN=CC=C11830.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nicotinuric acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CN=C11886.7Semi standard non polar33892256
Nicotinuric acid,1TMS,isomer #2C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CN=C11834.2Semi standard non polar33892256
Nicotinuric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C1821.7Semi standard non polar33892256
Nicotinuric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C1850.8Standard non polar33892256
Nicotinuric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C2263.9Standard polar33892256
Nicotinuric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CN=C12137.1Semi standard non polar33892256
Nicotinuric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CN=C12069.6Semi standard non polar33892256
Nicotinuric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C2287.6Semi standard non polar33892256
Nicotinuric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C2243.7Standard non polar33892256
Nicotinuric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C2500.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Nicotinuric acid GC-MS (2 TMS)splash10-0a4i-3950000000-4ea0184fb844e85c5f602014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nicotinuric acid GC-MS (Non-derivatized)splash10-0a4i-3950000000-4ea0184fb844e85c5f602017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nicotinuric acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0930000000-19848b215ab8a91b37d62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nicotinuric acid GC-EI-TOF (Non-derivatized)splash10-0a4i-0920000000-e5bc4a37c92cbe93c9262017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicotinuric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2900000000-27b6ba467f5df3c907722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicotinuric acid GC-MS (1 TMS) - 70eV, Positivesplash10-052r-6900000000-cbc193435481d138180a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicotinuric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicotinuric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001r-0900000000-28e9d6d719938b6ef2a02012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0550-4900000000-4b12baba3c8ed421aab42012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9000000000-ca65b11ed6964f642d972012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 10V, Positive-QTOFsplash10-001r-0900000000-2ea65649864830c4592d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 20V, Negative-QTOFsplash10-004i-9000000000-c350dfa18b26e812ddf62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 40V, Negative-QTOFsplash10-004i-9000000000-92176234045453c39e182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 10V, Negative-QTOFsplash10-004i-9400000000-2b06c9e150d173834b2b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 30V, Positive-QTOFsplash10-055r-5900000000-cbb63a133a2eca67da762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 10V, Positive-QTOFsplash10-001r-0900000000-a2d292d8b97e3068c1ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 10V, Positive-QTOFsplash10-001r-0900000000-01757174ec4bbbfe91872021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 0V, Positive-QTOFsplash10-001i-0900000000-e7ce537e2a3e5805fada2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 10V, Negative-QTOFsplash10-004r-7900000000-974123ca1d682fc003222021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 20V, Negative-QTOFsplash10-004i-9000000000-004cb59bf827d018b54c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 35V, Positive-QTOFsplash10-000i-0900000000-77b3ad5bcf7e7cd59a412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 30V, Positive-QTOFsplash10-0as0-8900000000-7572e92ecd0721514f7a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 30V, Negative-QTOFsplash10-004i-9000000000-42435d8b862daaa250fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 40V, Negative-QTOFsplash10-004i-9000000000-498fb0561add994d8bac2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 0V, Positive-QTOFsplash10-001i-0900000000-3ed1d19790df24452b112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotinuric acid 40V, Positive-QTOFsplash10-004i-9100000000-486a1f42c2a814cf32d52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinuric acid 10V, Positive-QTOFsplash10-001i-0900000000-7691658645b49efa12182015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinuric acid 20V, Positive-QTOFsplash10-01q0-1900000000-90da23067cff9198189d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinuric acid 40V, Positive-QTOFsplash10-0kai-9400000000-b6fb3beff4d893a45c9a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinuric acid 10V, Negative-QTOFsplash10-004i-0900000000-2e3fc586dec1a239f5802015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinuric acid 20V, Negative-QTOFsplash10-004i-2900000000-2e3ff3323d46a1520f5d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotinuric acid 40V, Negative-QTOFsplash10-004i-9200000000-053af4d9ef684962e67b2015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.00 +/- 1.67 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.33 (0.00 - 8.33) uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (24-38years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. Dieterle F, Ross A, Schlotterbeck G, Senn H: Metabolite projection analysis for fast identification of metabolites in metabonomics. Application in an amiodarone study. Anal Chem. 2006 Jun 1;78(11):3551-61. [PubMed:16737207 ]
  6. 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 ]

Enzymes

Enzyme Details
1. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Enzyme Details
2. Glycine N-acyltransferase-like protein 1
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
Enzyme Details
3. Glycine N-acyltransferase-like protein 2
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055
Enzyme Details
4. Glycine N-acyltransferase-like protein 3
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:
GLYATL3
Uniprot ID:
Q5SZD4
Molecular weight:
32703.3