Showing NP-Card for Niacinamide (NP0000925)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:41:09 UTC
NP-MRD IDNP0000925
Secondary Accession NumbersNone
Natural Product Identification
Common NameNiacinamide
DescriptionNiacinamide, also known as nicotinamide (NAM), is a form of vitamin B3 found in food and used as a dietary supplement and medication. Niacinamide belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. The structure of nicotinamide consists of a pyridine ring to which a primary amide group is attached in the meta position. It is an amide of nicotinic acid. As an aromatic compound, it undergoes electrophilic substitution reactions and transformations of its two functional groups. Niacinamide and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide and phosphate by the enzyme nicotinamide phosphoribosyltransferase. In humans, niacinamide is involved in the metabolic disorder called the nad+ signalling pathway (cancer). Niacinamide is an odorless tasting compound. Outside of the human body, niacinamide is found, on average, in the highest concentration within a few different foods, such as common sages, cow milk, and cocoa beans and in a lower concentration in common pea. Niacinamide has also been detected, but not quantified in several different foods, such as yardlong beans, roselles, apples, oyster mushrooms, and swiss chards. Niacinamide occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables. It is commonly added to cereals and other foods. Many multivitamins contain 20–30 mg of vitamin B3 and it is also available in higher doses. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000925 (Niacinamide)

  Mrv1652309042000222D          

  9  9  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
Download

3D MOL for NP0000925 (Niacinamide)

HMDB0001406
     RDKit          3D
Niacinamide
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.6884   -0.1205    0.1412 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    0.6582   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002    1.7424   -0.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2596    0.1906   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8422    0.9222   -0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102    0.4452   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103   -0.7385    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -1.4104    0.7817 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0321   -0.9897    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414    0.2561    0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8038   -1.0763   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6387    1.8393   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793    1.0035   -0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3086   -1.1382    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -1.5839    0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 10  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0000925 (Niacinamide)

  Mrv1652309042000222D          

  9  9  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000925

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)

> <INCHI_KEY>
DFPAKSUCGFBDDF-UHFFFAOYSA-N

> <FORMULA>
C6H6N2O

> <MOLECULAR_WEIGHT>
122.1246

> <EXACT_MASS>
122.048012824

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.711267443233845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridine-3-carboxamide

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-0.3937863166666665

> <ALOGPS_LOGS>
-0.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.38576188771524

> <JCHEM_PKA_STRONGEST_BASIC>
3.634895404358332

> <JCHEM_POLAR_SURFACE_AREA>
55.980000000000004

> <JCHEM_REFRACTIVITY>
32.979499999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nicotinamide

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0000925 (Niacinamide)

HMDB0001406
     RDKit          3D
Niacinamide
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.6884   -0.1205    0.1412 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    0.6582   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002    1.7424   -0.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2596    0.1906   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8422    0.9222   -0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102    0.4452   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103   -0.7385    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -1.4104    0.7817 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0321   -0.9897    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414    0.2561    0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8038   -1.0763   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6387    1.8393   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793    1.0035   -0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3086   -1.1382    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -1.5839    0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 10  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
M  END
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PDB for NP0000925 (Niacinamide)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0000925 (Niacinamide)

COMPND    HMDB0001406
HETATM    1  N1  UNL     1       2.688  -0.121   0.141  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.616   0.658  -0.335  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.800   1.742  -0.955  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.260   0.191  -0.101  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.842   0.922  -0.552  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.110   0.445  -0.310  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.310  -0.738   0.366  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.234  -1.410   0.782  1.00  0.00           N  
HETATM    9  C6  UNL     1       0.032  -0.990   0.573  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.341   0.256   0.841  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.804  -1.076  -0.227  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.639   1.839  -1.075  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.979   1.004  -0.655  1.00  0.00           H  
HETATM   14  H5  UNL     1      -3.309  -1.138   0.571  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.882  -1.584   0.937  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3    3    4
CONECT    4    5    5    9
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8   14
CONECT    8    9    9
CONECT    9   15
END
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SMILES for NP0000925 (Niacinamide)

NC(=O)C1=CC=CN=C1
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INCHI for NP0000925 (Niacinamide)

InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
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View in JSmol
Synonyms
Chemical FormulaC6H6N2O
Average Mass122.1246 Da
Monoisotopic Mass122.04801 Da
IUPAC Namepyridine-3-carboxamide
Traditional Namenicotinamide
CAS Registry Number98-92-0
SMILES
NC(=O)C1=CC=CN=C1
InChI Identifier
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
InChI KeyDFPAKSUCGFBDDF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-22View Spectrum
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-03View Spectrum
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
Alternative Parents
Substituents
  • Nicotinamide
  • Heteroaromatic compound
  • Primary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • 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 Point130 °CNot Available
Boiling Point334.41 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility500 mg/mL at 25 °CNot Available
LogP-0.37Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility50.1 g/LALOGPS
logP-0.45ALOGPS
logP-0.39ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)13.39ChemAxon
pKa (Strongest Basic)3.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.98 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.98 m³·mol⁻¹ChemAxon
Polarizability11.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001406
DrugBank IDDB02701
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012485
KNApSAcK IDC00000209
Chemspider ID911
KEGG Compound IDC00153
BioCyc IDNIACINAMIDE
BiGG ID34058
Wikipedia LinkNicotinamide
METLIN ID1497
PubChem Compound936
PDB IDNot Available
ChEBI ID17154
Good Scents IDrw1068911
References
General References