Showing metabocard for Nicotinic acid (MMDBc0000198)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:39:27 UTC
Update Date2024-09-27 21:54:25 UTC
Metabolite IDMMDBc0000198
Metabolite Identification
Common NameNicotinic acid
DescriptionNicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan (see below), but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb0acc4d08>

627
  Mrv1652309042000232D          

  9  9  0  0  0  0            999 V2000
    3.0790    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  6  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  9  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb0acc4d08>

HMDB0001488
     RDKit          3D
Nicotinic acid
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.5936   -1.2686    0.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9518   -0.1929    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6694    0.9781   -0.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997   -0.2461   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    0.9062   -0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060    0.8207   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -0.4146   -0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127   -1.5475   -0.0865 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -1.4534   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8564    1.5742    0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    1.8703   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1815    1.7291   -0.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183   -0.4023   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402   -2.3531    0.0491 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  2  0
  9  4  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
  9 14  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb0acc4d08>

627
  Mrv1652309042000232D          

  9  9  0  0  0  0            999 V2000
    3.0790    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  6  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  9  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000198

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)

> <INCHI_KEY>
PVNIIMVLHYAWGP-UHFFFAOYSA-N

> <FORMULA>
C6H5NO2

> <MOLECULAR_WEIGHT>
123.1094

> <EXACT_MASS>
123.032028409

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
11.303434426527051

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridine-3-carboxylic acid

> <ALOGPS_LOGP>
0.29

> <JCHEM_LOGP>
-0.16644564754087304

> <ALOGPS_LOGS>
-0.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.785610419861248

> <JCHEM_PKA_STRONGEST_BASIC>
4.193250855836253

> <JCHEM_POLAR_SURFACE_AREA>
50.19

> <JCHEM_REFRACTIVITY>
31.157299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
niacin

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb0acc4d08>

HMDB0001488
     RDKit          3D
Nicotinic acid
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.5936   -1.2686    0.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9518   -0.1929    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6694    0.9781   -0.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997   -0.2461   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    0.9062   -0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060    0.8207   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -0.4146   -0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127   -1.5475   -0.0865 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -1.4534   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8564    1.5742    0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    1.8703   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1815    1.7291   -0.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183   -0.4023   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402   -2.3531    0.0491 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  2  0
  9  4  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
  9 14  1  0
M  END
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PDB for #<Metabolite:0x00007fdb0acc4d08>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 627                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       5.747   2.218   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080   2.218   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       3.080  -2.402   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.414  -0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747  -0.862   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080  -0.862   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -2.402   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -3.172   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   1.448   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    6    8                                                       
CONECT    4    5    6    9                                                  
CONECT    5    4    7                                                       
CONECT    6    3    4                                                       
CONECT    7    5    8                                                       
CONECT    8    3    7                                                       
CONECT    9    1    2    4                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for #<Metabolite:0x00007fdb0acc4d08>

COMPND    HMDB0001488
HETATM    1  O1  UNL     1       2.594  -1.269   0.090  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.952  -0.193   0.000  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.669   0.978  -0.031  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.500  -0.246  -0.065  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.228   0.906  -0.162  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.606   0.821  -0.222  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.246  -0.415  -0.183  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.513  -1.548  -0.087  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.153  -1.453  -0.028  1.00  0.00           C  
HETATM   10  H1  UNL     1       2.856   1.574   0.763  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.235   1.870  -0.194  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.182   1.729  -0.299  1.00  0.00           H  
HETATM   13  H4  UNL     1      -3.318  -0.402  -0.234  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.440  -2.353   0.049  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    5    9
CONECT    5    6   11
CONECT    6    7    7   12
CONECT    7    8   13
CONECT    8    9    9
CONECT    9   14
END
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SMILES for #<Metabolite:0x00007fdb0acc4d08>

OC(=O)C1=CN=CC=C1
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INCHI for #<Metabolite:0x00007fdb0acc4d08>

InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
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Synonyms
ValueSource
3-CarboxypyridineChEBI
3-Pyridinecarboxylic acidChEBI
3-Pyridylcarboxylic acidChEBI
Acide nicotiniqueChEBI
Acido nicotinicoChEBI
Acidum nicotinicumChEBI
Anti-pellagra vitaminChEBI
beta-Pyridinecarboxylic acidChEBI
m-Pyridinecarboxylic acidChEBI
NiacinChEBI
NikotinsaeureChEBI
P.P. factorChEBI
Pellagra preventive factorChEBI
PP FactorChEBI
Pyridine-beta-carboxylic acidChEBI
Vitamin b3ChEBI
NiacorKegg
NiaspanKegg
3-PyridinecarboxylateGenerator
3-PyridylcarboxylateGenerator
b-PyridinecarboxylateGenerator
b-Pyridinecarboxylic acidGenerator
beta-PyridinecarboxylateGenerator
Β-pyridinecarboxylateGenerator
Β-pyridinecarboxylic acidGenerator
m-PyridinecarboxylateGenerator
Pyridine-b-carboxylateGenerator
Pyridine-b-carboxylic acidGenerator
Pyridine-beta-carboxylateGenerator
Pyridine-β-carboxylateGenerator
Pyridine-β-carboxylic acidGenerator
NicotinateGenerator
3-CarboxylpyridineHMDB
AkotinHMDB
ApelagrinHMDB
DaskilHMDB
EfacinHMDB
EnduracinHMDB
LinicHMDB
NiacHMDB
NiacineHMDB
NicacidHMDB
NicaminHMDB
NicanginHMDB
Nico-spanHMDB
NicobidHMDB
NicocapHMDB
NicodelmineHMDB
NicolarHMDB
NiconacidHMDB
Nicosan 3HMDB
NicotinipcaHMDB
NicylHMDB
NyclinHMDB
PellagrinHMDB
PeloninHMDB
Slo-niacinHMDB
WampocapHMDB
Aluminum salt, niacinHMDB
InduracinHMDB
Niacin cobalt (2+) saltHMDB
Niacin iron (2+) saltHMDB
Niacin lithium saltHMDB
Niacin magnesium saltHMDB
Niacin sodium saltHMDB
Nico-400HMDB
Potassium salt, niacinHMDB
Sodium salt, niacinHMDB
Tosylate, niacinHMDB
Nicotinate, lithiumHMDB
Hydrochloride, niacinHMDB
Niacin aluminum saltHMDB
Niacin calcium saltHMDB
Niacin copper (2+) saltHMDB
Niacin hydrochlorideHMDB
Niacin lithium salt, hemihydrateHMDB
Nico400HMDB
Tartrate, niacinHMDB
3 Pyridinecarboxylic acidHMDB
Lithium nicotinateHMDB
Niacin ammonium saltHMDB
Niacin manganese (2+) saltHMDB
Niacin potassium saltHMDB
Niacin tartrateHMDB
Niacin tosylateHMDB
Niacin zinc saltHMDB
Nico 400HMDB
Molecular FormulaC6H5NO2
Average Mass123.1094
Monoisotopic Mass123.032028409
IUPAC Namepyridine-3-carboxylic acid
Traditional Nameniacin
CAS Registry Number59-67-6
SMILES
OC(=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChI KeyPVNIIMVLHYAWGP-UHFFFAOYSA-N