Showing NP-Card for Nicotinic acid (NP0000614)

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Record Information
Version2.0
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
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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
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 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