Common NameNicotinamide
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
Molecular FormulaC6H6N2O
Average Mass122.12460
Monoisotopic Mass122.04801
IUPAC Namepyridine-3-carboxamide
Traditional NameNicotinamide
CAS Registry Number98-92-0
SMILESNC(=O)c1cccnc1
InChI IdentifierInChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
InChI KeyDFPAKSUCGFBDDF-UHFFFAOYSA-N
CHEBI IDCHEBI:17154
HMDB IDHMDB0001406
Pathways
NameSMPDB/PathBank
Nicotinate and nicotinamide metabolism
StateNot Available
Water Solubility5.01e+01 g/l
logP-0.45
logS-0.39
pKa (Strongest Acidic)13.39
pKa (Strongest Basic)3.63
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area55.98 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity32.98 m³·mol⁻¹
Polarizability11.71

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