General Information of MET (ID: META00436)
Name Nicotinic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
3 Pyridinecarboxylic acid; 3-Carboxylpyridine; 3-Carboxypyridine; 3-Pyridinecarboxylate; 3-Pyridinecarboxylic acid; 3-Pyridylcarboxylate; 3-Pyridylcarboxylic acid; Acide nicotinique; Acido nicotinico; Acidum nicotinicum; Akotin; Aluminum salt, niacin; Anti-pellagra vitamin; Apelagrin; Daskil; Efacin; Enduracin; Hydrochloride, niacin; Induracin; Linic; Lithium nicotinate; Niac; Niacin; Niacin aluminum salt; Niacin ammonium salt; Niacin calcium salt; Niacin cobalt (2+) salt; Niacin copper (2+) salt; Niacin hydrochloride; Niacin iron (2+) salt; Niacin lithium salt; Niacin lithium salt, hemihydrate; Niacin magnesium salt; Niacin manganese (2+) salt; Niacin potassium salt; Niacin sodium salt; Niacin tartrate; Niacin tosylate; Niacin zinc salt; Niacine; Niacor; Niaspan; Nicacid; Nicamin; Nicangin; Nico 400; Nico-400; Nico-span; Nico400; Nicobid; Nicocap; Nicodelmine; Nicolar; Niconacid; Nicosan 3; Nicotinate; Nicotinate, lithium; Nicotinipca; Nicyl; Nikotinsaeure; Nyclin; P.P. factor; PP Factor; Pellagra preventive factor; Pellagrin; Pelonin; Potassium salt, niacin; Pyridine-b-carboxylate; Pyridine-b-carboxylic acid; Pyridine-beta-carboxylic acid; Slo-niacin; Sodium salt, niacin; Tartrate, niacin; Tosylate, niacin; Vitamin b3; Wampocap; b-Pyridinecarboxylate; b-Pyridinecarboxylic acid; beta-Pyridinecarboxylic acid; m-Pyridinecarboxylate; m-Pyridinecarboxylic acid
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Carcinogenic Potency;Drug;Toxins/Pollutant;Cosmetic;Food additives;TCM Ingredients;Nicotinylsalicylic;acid;Microbial; ; Herbal Ingredients In-Vivo Metabolism
Structure Type   Pyridinecarboxylic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Pyridines and derivatives
Pyridinecarboxylic acids and derivatives
PubChem CID
938
HMDB ID
HMDB0001488
Formula
C6H5NO2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00253
DrugBank ID
DB00627
ChEBI ID
15940
FooDB ID
FDB001014
ChemSpider ID
913
METLIN ID
6272
Physicochemical Properties Molecular Weight 123.11 Topological Polar Surface Area 50.2
XlogP 0.4 Complexity 114
Heavy Atom Count 9 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Function
Nicotinic 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.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            Nicotinic acid receptor (HCAR2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Nicotinic acid addition (2 hours)
                      Induced Change HCAR2 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Diabetic acidosis [ICD-11: 5A22]
                      Details It is reported that nicotinic acid addition causes the increase of HCAR2 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Nicotinic acid concentration: increase (FC = 1.84 - 1.84)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of nicotinic acid levels compared with control group.
      Organic ion transporter (OIT)
            Solute carrier family 22 member 13 (SLC22A13) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Overexpression of SLC22A13
                      Induced Change Nicotinic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC22A13 leads to the increase of nicotinic acid levels compared with control group.
References
1 Deorphanization of GPR109B as a receptor for the beta-oxidation intermediate 3-OH-octanoic acid and its role in the regulation of lipolysis. J Biol Chem. 2009 Aug 14;284(33):21928-21933.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
3 Intestinal dehydroascorbic acid (DHA) transport mediated by the facilitative sugar transporters, GLUT2 and GLUT8. J Biol Chem. 2013 Mar 29;288(13):9092-101.

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