NIO

NICOTINIC ACID

Created:	1999-07-08
Last modified:	2024-10-02

Find Related PDB Entry
56 entries where NIO is found as a standalone ligand16 entries where NIO is found in a polymer sequence

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	14
Chiral Atom Count	0
Bond Count	14
Aromatic Bond Count	6

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	NICOTINIC ACID
Systematic Name (OpenEye OEToolkits)	pyridine-3-carboxylic acid
Formula	C₆ H₅ N O₂
Molecular Weight	123.109
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)c1cccnc1
SMILES	CACTVS	3.341	OC(=O)c1cccnc1
SMILES	OpenEye OEToolkits	1.5.0	c1cc(cnc1)C(=O)O
Canonical SMILES	CACTVS	3.341	OC(=O)c1cccnc1
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1cc(cnc1)C(=O)O
InChI	InChI	1.03	InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChIKey	InChI	1.03	PVNIIMVLHYAWGP-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB00627 ?
Name	Niacin
Groups	investigational approved nutraceutical
Description	Niacin is a B vitamin used to treat vitamin deficiencies as well as hyperlipidemia, dyslipidemia, hypertriglyceridemia, and to reduce the risk of myocardial infarctions.[L7550,L7553,L7556,L7559,L7562,L7565]
Synonyms	ácido nicotínico Niacin β-pyridinecarboxylic acid anti-pellagra vitamin 3-Pyridylcarboxylic acid Nicotinic acid 3-carboxypyridine Acide nicotinique 3-Pyridinecarboxylic acid pyridine-β-carboxylic acid Acidum Nicotinicum Niacina m-pyridinecarboxylic acid Nikotins?ure
Brand Names	Multi-actin Vita Balance 2000 Formula Hh Nitro Vites - Tab Nicaprin Only One - Tablet Vitamin B Complex Suppl Complex 5 - Pwr Swiss One Timed Release Tab Vita Vim With Beta Carotene-caplet Vitamin B Complex Tab Complete One A Day Tab Vita-vim With Beta-carotene - Tab Multivitamins and Minerals With Betacarotene Tablets Vitafol Plus Nutra Boost Phytopure Prenatal Harvest Of Values All B Complex Tab Cal M Tab Multi-Vitamin With Fluoride Natural Source Spectrum With Beta Carotene Davimet-M Multi-phyto Capsules OB Complete 400 Red American Eagle Vitamin Supplement Drink Simcor Animal Shapes Hyporyl - Tab Reno Caps Puralor Vitafol Caplet Acti-niacin Caplet 500mg Multi #2 Irospan 24/6 VITAFOL Gummies M-Natal Plus NESTABS ABC Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA Dothelle DHA Men's 50+ Lipo-B-C Tab Niacin 100mg Niaspan Hi Potency B Complex W Chelated Minerals Kindervites MVC-Fluoride Integra Plus Escavite D Formula F L W Grand Master Formula Tab Niacin-100 Tab 100mg Revitalize Multi-vitamin and Mineral Complex Vitamin B + C Cap bioJET Cc II Niacin Tab 100mg Multi Vitamines - Liq Usana Megavitamin Tablets - Tab Niacin 100 Mg Tablets Protect Cardio AF Nicazyme Abavite Davimet Provida OB Folivane-OB Multivit with Fluoride Lipall Plus Tab Card-floe II Tab Niacin 500 Mg and Inositol Iron Folate Plus TriStart DHA Multi-Vitamin Davimet with Fluoride Niacin Pwr 800mg/1.25ml Nephrocaps-QT Niacin Tab 100mg USP Sveets Antivert Tab B 6 Plus Ifb My Favorite Niacin and Inositol Tab Lustime Angel Bev 29 Tab Master Key Formula 3 Tab Integra Multivitamins and Minerals for Young Men Prenatal Formula Tab Extra Once A Day Prenatal Vitamins Plus Low Iron Stress Formula Multi-B Comp + 500mg Vit C Cap 24 Multivitamins + Minerals Niacin Cap 250mg Iron Folate-F Rogenic Taron-C DHA Provida DHA Folivane-Plus with Ascorbic Acid Precursors Myhephron Dialysis and Stress Supplement One A Day Advance Adults Formula Cw-caplet Multivitamins and Minerals for Young Women Vc II Niacin Tab 100mg Yeast Free Gesticare DHA Revit Multi-vitamins and Minerals Maxum Multi-vite Prenatal, DHA B6 Plus Tab Fusion Activator Formula Tab Niacin 100mg Tablets USP Super Stress Mega B Plus 1000mg Vit C Tab Niaspan Fct Niacin Tab 250mg Mega Vitaminerals Ultimate Tab Lip - Fac Formula Strovite Forte Caplet Vita Vim Multivitamins and Minerals Tab Remedium - Liq Orl Multi-Vitamin Fluoride and Iron Drops Novel Vita TL-Fluorivite Super Daily No 2 Formula Lf Master Key Multi Vitamin Multi Mineral Formula 2 Vege Swiss One Multivitamin W Chel Mins Tab Vitafol Fe Plus Niacin Tab 500mg Cavan Heme OB Fortistress Tab Vitafol OB Caplet Gtf-vitamin-minerals & Pancreatin Tab Orange Flavored Crystal Chews Tab Poly-Vi-Sol Cda-21 Vitamins With Non-medicinal Probiotic Complex Virt-C DHA Se-Natal Children's Chewable Tab NovaFerrum Multivitamin with Iron Pediatric Drops PreNatal Vitamins Plus Niacin 500mg Select OB Multi Tabs Niacin Nata Komplete O-Cal FA multivitamin Body Rox Vita-vim - Tab Iron 25mg With Vit B-cmplx, Vit C, Cu & Mo 50 Plus One A Day Advance Adults 50+ O-Cal Prenatal Vitamin PROTECT IRON Liquid Lipovitan Multivitamin with Fluoride Niacor Mega Capsules Pro Enz Tab American Eagle Energizer Plus Vitamin Supplement Drink Tri B3 Src 300mg Cavan Prenatal Gtf Support Caplet Iron, Vit & Min Supp Niacin Src 400mg C-B Complex Timed Release Vita-vim Srt WestGel DHA Multi Flow Tablets Lipotropic Ctr Multivitamin with fluoride Vitamin B Compound Tab Niacin Inj 100mg/ml Hemocyte Plus Concept DHA Niacin Ctr Srt 500mg DermaNIC Dr. AVi MULTIVITAMIN with Zinc, Real Ginger, Lemon and Lemongrass Vp-heme Ob DHA Maximum Once A Day Formula O.C. Ni-C-E-LE Plus Doctor's Choice Brand for Men Vitafol One Men's Lutime JEUNCELL Hair restorer and Hair Growth Solution NovaMV Multivitamin Vita B Complex Tab WesCap-C-DHA Sustained Release Niacin 500mg Tendera-OB Niacin Caps 100mg Vasodyn Tab Niodan 500 Mg Time Release Tablets Cool B Poly-Vi-Flor Gummies ahoSAN Fusion Plus Multi-Vitamin Fluoride Drops Vitafol-OB Plus DHA Prenatal Supplement Plus DHA Adeks Tablets Niaspan ER Multitabs Mega 13 Multivitamin Formula Genicin Vita-S Advicor Hsn Formula Mycelized Childrens Multi-vitamin Liq Vitamin & Mineral Formula 1 Dietary Supplement healthy mamaBE WELL ROUNDED BE WELL ROUNDED Niacin 50mg Niacin 250mg Vp-pnv-dha Pro Hers Vanilla Mhb Phytovim Cap Nephrocaps Prenatal Mega Antioxidant Integra F Armax B-complex Tab American Plus Energy & Vitamin Drink Flush Free Niacin With Inositol Formula Cp Cap Niacin 100mg Tab Niacin Tablets 500mg USP Red Bull B-3 500mg Continuous Released Formula # 7 Tab 50mg Daily-Vite Multi Vitamin-mineral Formula Multi-force for Women Tab Spectrum 2 Cap TriStart ONE Wellness Formula Vita Day Tab Shen Min Vitamin Supplement Escavite Lq Folivane-F Concept OB Niachrom Capsule Envirocomplex Niacin Tab 475mg Vita-Rx Diabetic Vitamin Vtb Vitamin and Mineral Supplement Vyo Cylate - Pwr Time Released Niacin 500 mg One Daily VITES Reaphirm Plant Source DHA Formula Cw B3 Chromemate Luna Vitamin and Mineral Bar for Women Metacinamide Tab Vitamin B3 Tab 10mg USP Chewable TriStart FREE Folika-T Vitalife - Capsule Multicaps Niacin-niacinamide Tab Protect Plus SO 60 Niacin 100 mg One-A-day Advance Men's Niacin Tab 50mg Innersource Tab Lustime Unicorn
Indication	Niacin is indicated to prevent vitamin deficiencies in pediatric and adult patients receiving parenteral nutrition as part of multivitamin intravenous injections.[L7550,L7553,L7556,L7559] Niacin oral tablets are indicated as a monotherapy or in combination with simvastatin or lovastatin to treat primary hyperlipidemia and mixed dyslipidemia.[L7562,L7565] It can also be used to reduce the risk of nonfatal myocardial infarctions in patients with a history of myocardial infarction and hyperlipidemia.[L7562,L7565] Niacin is also indicated with bile acid binding resins to treat atherosclerosis in patients with coronary artery disease and hyperlipidemia or to treat primary hyperlipidemia.[L7562,L7565] Finally niacin is indicated to treat severe hypertriglyceridemia.[L7562,L7565]
Categories	Agents Causing Muscle Toxicity Cardiovascular Agents Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Diet, Food, and Nutrition Food Growth Substances Hyperglycemia-Associated Agents Hypolipidemic Agents Hypolipidemic Agents Indicated for Hyperlipidemia Lipid Modifying Agents Lipid Modifying Agents, Plain Lipid Regulating Agents Micronutrients Miscellaneous Antilipemic Agents Nicotinic Acid and Derivatives Nicotinic Acids Non-statin Hypolipidemic Agents Indicated for Hyperlipidemia Noxae Organic Anion Transporting Polypeptide 2B1 Inhibitors Peripheral Vasodilators Physiological Phenomena Pyridines Thyroxine-binding globulin inhibitors Toxic Actions Vasodilating Agents Vitamin B Complex Vitamins
ATC-Code	C10AD02 C10AD52 C10BA01 C04AC01
CAS number	59-67-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Hydroxycarboxylic acid receptor 3	MNRHHLQDHFLEIDKKNCCVFRDDFIAKVLPPVLGLEFIFGLLGNGLALW...	unknown	agonist
Diacylglycerol O-acyltransferase 2	MKTLIAAYSGVLRGERQAEADRSQRSHGGPALSREGSGRWGTGSSILSAL...	unknown	inhibitor
Hydroxycarboxylic acid receptor 2	MNRHHLQDHFLEIDKKNCCVFRDDFIVKVLPPVLGLEFIFGLLGNGLALW...	unknown	agonist
Nicotinate-nucleotide pyrophosphorylase [carboxylating]	MDAEGLALLLPPVTLAALVDSWLREDCPGLNYAALVSGAGPSQAALWAKS...	unknown	binder
Nicotinamide N-methyltransferase	MESGFTSKDTYLSHFNPRDYLEKYYKFGSRHSAESQILKHLLKNLFKIFC...	unknown	binder
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	inhibitor
Thyroxine-binding globulin	MSPFLYLVLLVLGLHATIHCASPEGKVTACHSSQPNATLYKMSSINADFA...	unknown	inhibitor
Organic cation/carnitine transporter 2	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	inhibitor
Monocarboxylate transporter 1	MPPAVGGPVGYTPPDGGWGWAVVIGAFISIGFSYAFPKSITVFFKEIEGI...	unknown	substrate
Sodium-coupled monocarboxylate transporter 1	MDTPRGIGTFVVWDYVVFAGMLVISAAIGIYYAFAGGGQQTSKDFLMGGR...	unknown
Monocarboxylate transporter 4	MGGAVVDEGPTGVKAPDGGWGWAVLFGCFVITGFSYAFPKAVSVFFKELI...	unknown
View More

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682