Np mrd loader

Showing NP-Card for Nicotinic acid (NP0000614)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:01 UTC
NP-MRD IDNP0000614
Secondary Accession NumbersNone
Natural Product 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, 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000614 (Nicotinic acid)

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
Download

3D MOL for NP0000614 (Nicotinic acid)

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
Download

3D SDF for NP0000614 (Nicotinic acid)

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>
NP0000614

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000614 (Nicotinic acid)

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
Download

PDB for NP0000614 (Nicotinic acid)

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
Download

3D PDB for NP0000614 (Nicotinic acid)

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 NP0000614 (Nicotinic acid)

OC(=O)C1=CN=CC=C1
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INCHI for NP0000614 (Nicotinic acid)

InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
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View in JSmol
Synonyms
ValueSource
3-CarboxylpyridineChEBI
3-CarboxypyridineChEBI
3-Pyridinecarboxylic acidChEBI
3-Pyridylcarboxylic acidChEBI
Acide nicotiniqueChEBI
Acido nicotinicoChEBI
Acidum nicotinicumChEBI
Anti-pellagra vitaminChEBI
beta-Pyridinecarboxylic acidChEBI
m-Pyridinecarboxylic acidChEBI
NiacinChEBI
NiacorChEBI
NiaspanChEBI
NicotinsaureChEBI
NikotinsaeureChEBI
P.P. factorChEBI
Pellagra preventive factorChEBI
PP FactorChEBI
Pyridine-beta-carboxylic acidChEBI
Pyridine-carboxylique-3ChEBI
Vitamin b3ChEBI
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
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
Chemical FormulaC6H5NO2
Average Mass123.1094 Da
Monoisotopic Mass123.03203 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 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
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenserFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Ajuga taiwanensisKNApSAcK Database
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Alosa sapidissimaFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anemarrhena asphodeloidesKNApSAcK Database
Anethum graveolensFooDB
Angelica acutilobaLOTUS Database
Angelica keiskeiFooDB
Angelica sinensisKNApSAcK Database
AnguillaFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anoplopoma fimbriaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Aplodinotus grunniensFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arbutus unedoLOTUS Database
Archosargus probatocephalusFooDB
Arctium lappaFooDB
Areca catechuLOTUS Database
Aristolochia kaempferiLOTUS Database
Armoracia rusticanaFooDB
Artemia salinaLOTUS Database
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Begonia nantoensisKNApSAcK Database
Belone beloneFooDB
Benincasa hispidaKNApSAcK Database
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
BivalviaFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
BrachyuraFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea L. ssp. BotrytisKNApSAcK Database
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Brosme brosmeFooDB
Bubalus bubalisFooDB
BuccinidaeFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Callinectes sapidusFooDB
Canarium ovatumFooDB
Cancer magisterFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
Cassytha filiformisKNApSAcK Database
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catostomus commersoniiFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chanos chanosFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chionoecetes opilioFooDB
Chondrus crispusFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clinocardium nuttalliiFooDB
Clupea harengus harengusFooDB
Clupea pallasiiFooDB
ClupeinaeFooDB
Cocos nuciferaFooDB
Codonopsis pilosulaKNApSAcK Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
Colocasia escultentaPlant
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
CoregonusFooDB
Coregonus artediFooDB
Coregonus nasusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Cyprinus carpioKNApSAcK Database
Dallia pectoralisFooDB
Datura metelLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea alataKNApSAcK Database
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
EngraulidaeFooDB
Engraulis encrasicolusFooDB
Enteroctopus dofleiniFooDB
EpinephelusFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
EucheumaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eurycoma longifoliaLOTUS Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gadus morhuaFooDB
Galanthus trojanusLOTUS Database
Gallus gallusFooDB
Garcinia mangostanaFooDB
GastropodaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxKNApSAcK Database
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoidesFooDB
Homarus americanusFooDB
Homo sapiensLOTUS Database
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Ictalurus punctatusFooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Katsuwonus pelamisFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
    • DG. Criossby. The Organic Constituents of Food. I. Lettuce. J. Food Sci. 1963, 28(3):347-355
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
LaminariaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Leiostomus xanthurusFooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
Lepomis gibbosusFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lophius piscatoriusFooDB
Lopholatilus chamaeleonticepsFooDB
Lota lotaFooDB
Lotus corniculatusLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
LutjanidaeFooDB
Lycium chinenseKNApSAcK Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaKNApSAcK Database
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaKNApSAcK Database
Melanitta fuscaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Micromesistius poutassouFooDB
Micropogonias undulatusFooDB
Microstomus kittFooDB
Molva molvaFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
Morone saxatilisFooDB
MorusFooDB
Morus nigraFooDB
Mugil cephalusFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyoxocephalusFooDB
MyricaFooDB
Myristica fragransFooDB
MytilidaeFooDB
Mytilus edulisFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Nicotiana plumbaginifoliaLOTUS Database
Nicotiana tabacumKNApSAcK Database
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
Octopus vulgarisFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OncorhynchusFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
Ophiocordyceps sinensisLOTUS Database
Ophiodon elongatusFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Osmerus mordaxFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
PalinuridaeFooDB
Panax ginsengKNApSAcK Database
Pangium eduleFooDB
Panicum miliaceumFooDB
PapaverFooDB
Paralithodes camtschaticusFooDB
Parastichopus californicusFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PectinidaeFooDB
Pediomelum esculentumFooDB
Peprilus triacanthusFooDB
PerciformesFooDB
PercoideiFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus citrinopileatusLOTUS Database
Pleurotus ostreatusFooDB
PollachiusFooDB
Pollachius pollachiusFooDB
Polygonum alpinumFooDB
Pomatomus saltatrixFooDB
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
RanidaeFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Saccharina japonicaFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salmo salarFooDB
Salmo trutta forma truttaFooDB
Salmonella entericaLOTUS Database
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scomberomorus cavallaFooDB
Scomberomorus maculatusFooDB
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
SebastesFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
SepiidaeFooDB
Seriola lalandiFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
SiluriformesFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
SoleidaeFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
SpirulinaFooDB
SqualiformesFooDB
Squalus acanthiasFooDB
Stenodus leucichthysFooDB
Stenotomus chrysopsFooDB
StrombidaeFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaKNApSAcK Database
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
TeuthidaFooDB
ThelespermaFooDB
Theobroma cacaoFooDB
ThunnusFooDB
Thunnus albacaresFooDB
Thunnus thynnusFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Trachinotus carolinusFooDB
Trachurus symmetricusFooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
TunicataFooDB
Typha angustifoliaFooDB
Umbelopsis vinaceaLOTUS Database
Undaria pinnatifidaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Virola surinamensisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Xiphias gladiusFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus jujubaKNApSAcK Database
Ziziphus zizyphusFooDB
Zoarces americanusFooDB
Species Where Detected
Species NameSourceReference
Bombyx moriKNApSAcK Database
Bos taurus domesticusKNApSAcK Database
Escherichia coliKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Mortierella vinaceaKNApSAcK Database
Porphyra teneraKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point236.6 °CNot Available
Boiling Point292.47 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility18 mg/mLNot Available
LogP0.36Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility83.1 g/LALOGPS
logP0.29ALOGPS
logP-0.17ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.16 m³·mol⁻¹ChemAxon
Polarizability11.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001488
DrugBank IDDB00627
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003781
KNApSAcK IDC00000208
Chemspider ID913
KEGG Compound IDC00253
BioCyc IDNIACINE
BiGG ID34401
Wikipedia LinkNiacin
METLIN ID6272
PubChem Compound938
PDB IDNot Available
ChEBI ID15940
Good Scents IDrw1099331
References
General References
  1. Tunaru S, Kero J, Schaub A, Wufka C, Blaukat A, Pfeffer K, Offermanns S: PUMA-G and HM74 are receptors for nicotinic acid and mediate its anti-lipolytic effect. Nat Med. 2003 Mar;9(3):352-5. Epub 2003 Feb 3. [PubMed:12563315 ]
  2. Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59. [PubMed:182198 ]
  3. Salvi A, Carrupt PA, Mayer JM, Testa B: Esterase-like activity of human serum albumin toward prodrug esters of nicotinic acid. Drug Metab Dispos. 1997 Apr;25(4):395-8. [PubMed:9107536 ]
  4. Hertle H, Kiese M, Renner G: Absorption in rats, dogs, pigs, and humans of nicotinic acid after oral administration of phosphatidyl inositol pentanicotinate hydrochloride (PIN). Arzneimittelforschung. 1979;29(1):114-6. [PubMed:582105 ]
  5. Zarzycki PK, Kowalski P, Nowakowska J, Lamparczyk H: High-performance liquid chromatographic and capillary electrophoretic determination of free nicotinic acid in human plasma and separation of its metabolites by capillary electrophoresis. J Chromatogr A. 1995 Aug 11;709(1):203-8. [PubMed:7581845 ]
  6. 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 ]
  7. Santos RD: [Pharmacology of niacin or nicotinic acid]. Arq Bras Cardiol. 2005 Oct;85 Suppl 5:17-9. Epub 2006 Jan 2. [PubMed:16400392 ]
  8. Mrochek JE, Jolley RL, Young DS, Turner WJ: Metabolic response of humans to ingestion of nicotinic acid and nicotinamide. Clin Chem. 1976 Nov;22(11):1821-7. [PubMed:135660 ]
  9. Pike NB: Flushing out the role of GPR109A (HM74A) in the clinical efficacy of nicotinic acid. J Clin Invest. 2005 Dec;115(12):3400-3. [PubMed:16322787 ]
  10. Kobayashi M, Shimizu S: [Nicotinic acid and nicotinamide]. Nihon Rinsho. 1999 Oct;57(10):2211-7. [PubMed:10540864 ]
  11. Sutherland WH, Larking PW, Nye ER: Modification of nicotinic acid and prostaglandin E1 antilipolytic action in vitro. Atherosclerosis. 1976 Oct;25(1):45-53. [PubMed:186078 ]
  12. Stratford MR, Dennis MF, Hoskin P, Phillips H, Hodgkiss RJ, Rojas A: Nicotinamide pharmacokinetics in humans: effect of gastric acid inhibition, comparison of rectal vs oral administration and the use of saliva for drug monitoring. Br J Cancer. 1996 Jul;74(1):16-21. [PubMed:8679452 ]
  13. Angelin B, Einarsson K, Leijd B: Biliary lipid composition during treatment with different hypolipidaemic drugs. Eur J Clin Invest. 1979 Jun;9(3):185-90. [PubMed:113218 ]
  14. Patterson MC, Di Bisceglie AM, Higgins JJ, Abel RB, Schiffmann R, Parker CC, Argoff CE, Grewal RP, Yu K, Pentchev PG, et al.: The effect of cholesterol-lowering agents on hepatic and plasma cholesterol in Niemann-Pick disease type C. Neurology. 1993 Jan;43(1):61-4. [PubMed:8423912 ]
  15. Muller B, Kasper M, Surber C, Imanidis G: Permeation, metabolism and site of action concentration of nicotinic acid derivatives in human skin. Correlation with topical pharmacological effect. Eur J Pharm Sci. 2003 Oct;20(2):181-95. [PubMed:14550884 ]
  16. Chekalina SI, Guseva LI, Bardyechev MS: [Use of nicotinic acid and midocalm for correcting blood coagulation in patients with radiation edema of the extremities]. Med Radiol (Mosk). 1985 Aug;30(8):28-30. [PubMed:4033386 ]
  17. Gopal E, Fei YJ, Miyauchi S, Zhuang L, Prasad PD, Ganapathy V: Sodium-coupled and electrogenic transport of B-complex vitamin nicotinic acid by slc5a8, a member of the Na/glucose co-transporter gene family. Biochem J. 2005 May 15;388(Pt 1):309-16. [PubMed:15651982 ]