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

WebGL does not seem to be available.

This can be caused by an outdated browser, graphics card driver issue, or bad weather. Sometimes, just restarting the browser helps. Also, make sure hardware acceleration is enabled in your browser.

For a list of supported browsers, refer to http://caniuse.com/#feat=webgl.

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 data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

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

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

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