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	approved investigational 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	Nicotinic acid β-pyridinecarboxylic acid Acide nicotinique Niacin Nikotins?ure ácido nicotínico 3-Pyridylcarboxylic acid pyridine-β-carboxylic acid Acidum Nicotinicum Niacina 3-Pyridinecarboxylic acid 3-carboxypyridine m-pyridinecarboxylic acid anti-pellagra vitamin
Brand Names	M-Natal Plus Super Stress Mega B Plus 1000mg Vit C Tab Red American Eagle Vitamin Supplement Drink Virt-C DHA Nephrocaps ahoSAN DermaNIC Natural Source Spectrum With Beta Carotene O-Cal FA multivitamin Revit Multi-vitamins and Minerals Tendera-OB Vitafol-OB Plus DHA Prenatal Supplement Plus DHA MVC-Fluoride Ni-C-E-LE Plus Nicaprin Mega Capsules Dr. AVi MULTIVITAMIN with Zinc, Real Ginger, Lemon and Lemongrass Formula Cw-caplet Prenatal, DHA Card-floe II Tab Escavite D Multivit with Fluoride Formula Cw NESTABS ABC Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA Niacin 250mg Niacor O-Cal Prenatal Vitamin Prenatal Provida DHA Select OB Lustime Unicorn Fortistress Tab Niacin Tablets 500mg USP Vita Day Tab TriStart FREE Multi Tabs B 6 Plus Complex 5 - Pwr Gtf-vitamin-minerals & Pancreatin Tab One-A-day Advance Men's Harvest Of Values All B Complex Tab Vitafol Caplet Niaspan Fct Master Key Formula 3 Tab Niaspan ER Niacin Ctr Srt 500mg Niacin 50mg Multitabs JEUNCELL Hair restorer and Hair Growth Solution Niacin Mycelized Childrens Multi-vitamin Liq Tri B3 Src 300mg Nata Komplete Multi Flow Tablets Vitamin & Mineral Formula 1 Dietary Supplement Niacin Tab 250mg Davimet with Fluoride Folivane-OB Se-Natal Prenatal Mega Antioxidant Vitamin B Compound Tab Fusion Activator Formula Tab Vitamin B Complex Suppl Antivert Tab Men's My Favorite Niacin and Inositol Tab Niacin Caps 100mg Wellness Formula Multi-Vitamin Fluoride and Iron Drops Davimet TriStart DHA Cda-21 Vitamins With Non-medicinal Probiotic Complex Vita-Rx Diabetic Vitamin Niacin 100 mg Vitafol OB Caplet Cal M Tab Vc II Nitro Vites - Tab Complete One A Day Tab Red Bull Metacinamide Tab WesCap-C-DHA Multi Vitamin-mineral Formula Niacin 500mg Hemocyte Plus Gtf Support Caplet B6 Plus Tab Cc II Gesticare DHA Phytopure Niaspan Luna Vitamin and Mineral Bar for Women Multi-actin VITAFOL Gummies Niacin 100mg Genicin Vita-S Vita B Complex Tab Concept DHA Prenatal Vitamins Plus Low Iron Puralor American Plus Energy & Vitamin Drink Mhb Niacin Tab 50mg Maxum Multi-vite Children's Chewable Tab WestGel DHA Niacin Pwr 800mg/1.25ml Adeks Tablets 24 Multivitamins + Minerals Usana Megavitamin Tablets - Tab Escavite Lq Chromemate Poly-Vi-Flor Gummies Davimet-M Multivitamins and Minerals With Betacarotene Tablets Nicazyme Mega Vitaminerals Niacin Tab 100mg Envirocomplex Lipotropic Ctr Folivane-F Multivitamin with Fluoride Niacin Tab 100mg USP Folika-T Myhephron Dialysis and Stress Supplement Reno Caps Vyo Cylate - Pwr Vitafol One Simcor Niacin 100mg Tab C-B Complex healthy mamaBE WELL ROUNDED BE WELL ROUNDED Men's 50+ 50 Plus Multi #2 Cavan Heme OB Lipo-B-C Tab Reaphirm Plant Source DHA Cool B Formula Hh Grand Master Formula Tab Daily-Vite Vitafol Fe Plus B-complex Tab One A Day Advance Adults Master Key Multi Vitamin Multi Mineral Formula 2 Niacin Tab 475mg Vitamin B + C Cap Integra F Abavite Body Rox Formula Lf Vita-vim - Tab Integra Plus Niodan 500 Mg Time Release Tablets Lip - Fac Formula Vitamin B Complex Tab Spectrum 2 Cap Iron, Vit & Min Supp Super Daily No 2 Vitafol Plus PreNatal Vitamins Plus Iron 25mg With Vit B-cmplx, Vit C, Cu & Mo Multi-Vitamin With Fluoride Cavan Prenatal American Eagle Energizer Plus Vitamin Supplement Drink Integra Innersource Tab Fusion Plus Ifb Pro Hers Vanilla Shen Min Vitamin Supplement Stress Formula Multi-B Comp + 500mg Vit C Cap Time Released Niacin 500 mg Advicor Concept OB Niacin 100 Mg Tablets Multi-force for Women Tab Niacin 100mg Tablets USP Novel Vita Hsn Formula Mega 13 Multivitamin Formula Only One - Tablet Protect Cardio AF Sveets Vita Vim Multivitamins and Minerals Tab Vita Balance 2000 Revitalize Multi-vitamin and Mineral Complex Kindervites Lutime Multi Vitamines - Liq Multivitamins and Minerals for Young Women bioJET Irospan 24/6 Lipall Plus Tab Bev 29 Tab Vtb Vitamin and Mineral Supplement Formula O.C. Multicaps PROTECT IRON Liquid Sustained Release Niacin 500mg Vitalife - Capsule Niacin Src 400mg Vege Swiss One Multivitamin W Chel Mins Tab Armax Multi-phyto Capsules Vp-heme Ob DHA Vasodyn Tab Poly-Vi-Sol B3 Timed Release Vita-vim Srt TriStart ONE Niacin Tab 500mg OB Complete 400 One Daily VITES Niacin-100 Tab 100mg Lustime Angel Prenatal Formula Tab Multivitamin with fluoride Niachrom Capsule Multi-Vitamin Iron Folate-F Vita Vim With Beta Carotene-caplet Niacin Tab 100mg Yeast Free Flush Free Niacin With Inositol Taron-C DHA Formula F L W NovaMV Multivitamin Vp-pnv-dha One A Day Advance Adults 50+ Iron Folate Plus Multi-Vitamin Fluoride Drops Niacin Inj 100mg/ml Niacin 500 Mg and Inositol B-3 500mg Continuous Released Orange Flavored Crystal Chews Tab Niacin Cap 250mg Vitamin B3 Tab 10mg USP Chewable Hi Potency B Complex W Chelated Minerals Phytovim Cap Strovite Forte Caplet Dothelle DHA Niacin-niacinamide Tab TL-Fluorivite Animal Shapes Doctor's Choice Brand for Men Provida OB Rogenic Nephrocaps-QT Multivitamins and Minerals for Young Men Formula # 7 Tab 50mg Lipovitan Extra Once A Day Folivane-Plus with Ascorbic Acid Precursors Nutra Boost Hyporyl - Tab Remedium - Liq Orl Pro Enz Tab Ultimate Tab Swiss One Timed Release Tab Vita-vim With Beta-carotene - Tab Protect Plus SO 60 Maximum Once A Day Acti-niacin Caplet 500mg Formula Cp Cap NovaFerrum Multivitamin with Iron Pediatric Drops
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