Compound: nicotinic acid
SMILES: O=C(O)c1cnccc1
InChIKey: PVNIIMVLHYAWGP-UHFFFAOYSA-N
Synonyms: nicotinic acid, niacin, 59-67-6, Pyridine-3-carboxylic acid, 3-pyridinecarboxylic acid, 3-Carboxypyridine, vitamin B3, wampocap, Apelagrin, Pellagrin, Akotin, Daskil, Efacin, Niaspan, Pelonin, Linic, nicolar, Nicotinipca, Nicacid, Nicangin, Niconacid, Nyclin, Nicyl, Acidum nicotinicum, Nico-Span, Direktan, Nicodelmine, Pellagramin, Bionic, Diacin, Peviton, Niac, Nicosan 3, Davitamon PP, Vitaplex N, nicamin, nicobid, nicocap, Tega-Span, Enduracin, Nicocidin, Nicocrisina, Niconazid, Nicotamin, Nicovasan, Nicovasen, Nicodon, Niconat, Nicorol, Nicosyl, Nicotene, Nicotil, Nipellen, SK-Niacin, Naotin, Niacor, Tinic, 3-Carboxylpyridine, Nicotine acid, Slo-niacin, Acide nicotinique, NICO, Nicotinsaure, Nicagin, Pyridine-beta-carboxylic acid, Acido nicotinico, anti-Pellagra vitamin, PP Factor, Kyselina nikotinova, P.P. factor, S115, 3-Pyridylcarboxylic acid, m-Pyridinecarboxylic acid, Pellagra preventive factor, niacine, Pyridine-carboxylique-3, EPA Pesticide Chemical Code 056701, Niacin extended release, Nikotinsaeure, SR 4390, beta-pyridinecarboxylic acid, NIASPAN TITRATION STARTER PACK, NSC-169454, Niacin (USP), Niacin [USP], DTXSID1020932, VITAMIN B-3, 2679MF687A, DTXCID10932, CHEBI:15940, NSC169454, 3 Pyridinecarboxylic Acid, Niacin Td, Niaspan ER, Tartrate, Niacin, Tosylate, Niacin, Nicotinate, Lithium, Sodium Salt, Niacin, Hydrochloride, Niacin, Aluminum Salt, Niacin, Nico400, Potassium Salt, Niacin, Nico 400, RefChem:927738, hydron;pyridine-3-carboxylate, CHEBI:176839, Jeuncell Hair Restorer and Hair Growth Solution, 200-441-0, 681-634-0, 3-Picolinic acid, Nico-400, Caswell No. 598, Nicotinsaure [German], MFCD00006391, Kyselina nikotinova [Czech], CCRIS 1902, Acide nicotinique [INN-French], Acido nicotinico [INN-Spanish], Acidum nicotinicum [INN-Latin], HSDB 3134, Pyridine-carboxylique-3 [French], AI3-18994, Pyridinecarboxylic acid, 3-, BRN 0109591, Nicotinic acid [INN], NAH, CHEMBL573, MLS000069603, Pyridine-.beta.-carboxylic acid, P.P. factor-pellagra preventive factor, CAS-59-67-6, pyridine, 3-carboxy-, NCGC00016268-02, SMR000059024, [5, 6-3H]-niacin, Niacin [USAN], Nicotinicacid, Niacin (nicotinic acid), SR-01000722017, EINECS 200-441-0, NSC 169454, Nicotinic Acid;, UNII-2679MF687A, preventative factor, Nicotinic acid RS, antipellagra vitamin, Nicotinic acid CRS, Niaspan (TN), 3-Pyridylcarboxylate, 3PyrCOOH, [3H]nicotinic acid, Niacor (TN), [3H]-Nicotinic acid, Spectrum_001063, pyridinium-3-carboxylate, NIACIN [VANDF], NIACIN [HSDB], Nicotinic acid (Niacin), 5-pyridinecarboxylic acid, NIACIN [FCC], NIACIN [USP-RS], Opera_ID_1346, Prestwick0_000881, Prestwick1_000881, Prestwick2_000881, Prestwick3_000881, Pyridine-3-carbonic acid, Spectrum2_000006, Spectrum3_000515, Spectrum4_000965, Spectrum5_001287, Nicotinamide Impurity 16, 3-Pyridyl carboxylic acid, Nicotinic acid-13C1 ), Nicotinic acid-d3(major), WLN: T6NJ CVQ, 3-pyridine carboxylic acid, bmse000104, Nicotinic acid, >=98%, Nicotinic acid, USP grade, EC 200-441-0, SCHEMBL1433, NICOTINIC ACID [MI], Oprea1_514398, VITAMIN B3 [VANDF], BSPBio_000662, BSPBio_002069, KBioGR_001309, KBioSS_001543, NIACIN [ORANGE BOOK], NICOTINIC ACID [JAN], 5-22-02-00057 (Beilstein Handbook Reference), Nicotinic acid (Vitamin B3), BIDD:GT0644, DivK1c_000695, Nicotinic acid (JP18/INN), SCHEMBL308467, SCHEMBL309891, SCHEMBL333960, SCHEMBL658420, SIMCOR COMPONENT NIACIN, SPECTRUM1500430, .beta.-Pyridinecarboxylic acid, SPBio_000011, SPBio_002881, ADVICOR COMPONENT NIACIN, NIACIN [USP MONOGRAPH], NICOTINIC ACID [VANDF], BPBio1_000730, GTPL1588, GTPL1594, orb1310206, orb3139920, SCHEMBL2045277, NICOTINIC ACID [MART.], NICOTINIC ACID [WHO-DD], NICOTINIC ACID [WHO-IP], SCHEMBL29349574, BDBM23515, HMS502C17, KBio1_000695, KBio2_001543, KBio2_004111, KBio2_006679, KBio3_001569, ABT-919, MSK1518, NICOTINIC ACID [EMA EPAR], NINDS_000695, HMS1570B04, HMS1920P17, HMS2091H22, HMS2097B04, HMS2236A05, HMS3259K21, HMS3371E07, HMS3655K08, HMS3714B04, HMS5079H22, Pharmakon1600-01500430, Nicotinic acid, analytical standard, HCA98714, HY-B0143, STR00112, Tox21_110337, Tox21_201420, Tox21_302904, AC8691, BBL037343, CCG-38340, EBC-00528, NICOTINIC ACID [EP IMPURITY], Nicotinic acid, for synthesis, 99%, NSC757241, s1744, SBB004279, STK301803, NICOTINIC ACID [EP MONOGRAPH], AKOS000118980, Nicotinic acid, >=99.5% (HPLC), Tox21_110337_1, CS-1946, DB00627, FN16182, NC00524, Nicotinic Acid 1.0 mg/ml in Methanol, NSC-757241, PS-4255, SDCCGMLS-0066610.P001, IDI1_000695, NCGC00016268-01, NCGC00016268-03, NCGC00016268-04, NCGC00016268-05, NCGC00016268-08, NCGC00016268-09, NCGC00016268-13, NCGC00094734-01, NCGC00094734-02, NCGC00256537-01, NCGC00258971-01, AC-22484, ACIDUM NICOTINICUM [WHO-IP LATIN], BP-21419, NCI60_001041, Nicotinic acid, plant cell culture tested, ST097540, SY011111, SBI-0051456.P003, DB-007765, Nicotinic Acid [Matrix for MALDI-TOF/MS], AB00052050, N0082, N1103, Nicotinic acid 10 microg/mL in Acetonitrile, Nicotinic acid, purum, >=99.0% (HPLC), NS00003500, SW197229-3, EN300-16693, C00253, D00049, Nicotinic acid(Discontinued,See C4X-200016), Nicotinic acid, SAJ special grade, >=99.5%, AB00052050-13, AB00052050_14, AB00052050_15, Nicotinic acid, meets USP testing specifications, AC-907/25014105, AE-641/00368010, F214893, L001199, METHYL NICOTINATE IMPURITY A [EP IMPURITY], Nicorandil Impurity 3; Nicotinamide EP Impurity A, Q134658, SR-01000722017-2, SR-01000722017-3, SR-01000722017-4, BRD-K60237333-001-26-3, BRD-K60237333-001-27-1, BRD-K60237333-001-28-9, Z56755709, 3DDB011E-F3A6-45B6-A2D2-77B2A6E8936E, F2191-0082, Niacin, United States Pharmacopeia (USP) Reference Standard, Nicotinic acid, certified reference material, TraceCERT(R), Nicotinic acid, European Pharmacopoeia (EP) Reference Standard, Nicotinic acid, matrix substance for MALDI-MS, >=99.5% (HPLC), InChI=1/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9, Nicotinic acid, for inorganic trace analysis, >=99.999% (metals basis), Niacin (Nicotinic Acid), Pharmaceutical Secondary Standard; Certified Reference Material, 101113-41-1, Nicotinic acid, BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture, >=98%
Theoretical properties:
molecular_formula: C6H5NO2
molecular_weight: 123.11 g/mol
exact_mass: 123.032028402 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 9
topological_polar_surface_area: 50.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Needles from alcohol or water
color: Needles from alcohol or water
odor: Odorless
boiling_point: Sublimes (NTP, 1992)
melting_point: 457 °F (NTP, 1992)
density: 1.473 (NTP, 1992) - Denser than water; will sink
solubility: 10 to 50 mg/mL at 63 °F (NTP, 1992)
flash_point: 193 °C (379 °F) - closed cup
vapor_pressure: 0.0000057 [mmHg]
Descriptions:
{"pubchem": "Nicotinic acid is a pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group. It has a role as a metabolite, a vasodilator agent, an antilipemic drug, an antidote, a mouse metabolite, a plant metabolite, an Escherichia coli metabolite, a human urinary metabolite and an EC 3.5.1.19 (nicotinamidase) inhibitor. It is a vitamin B3, a pyridine alkaloid and a pyridinemonocarboxylic acid. It is a conjugate acid of a nicotinate.", "chebi": "A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.", "chembl": "NIACIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Nicotinic acid, or niacin, is an organic compound and a vitamer of vitamin B3, an essential human nutrient. It is produced by plants and animals from the amino acid tryptophan.\nNicotinic acid is also a prescription medication. Amounts far in excess of the recommended dietary intake for vitamin functions will lower blood triglycerides and low density lipoprotein cholesterol (LDL-C), and raise blood high density lipoprotein cholesterol (HDL-C, often referred to as \"good\" cholesterol). There are two forms: immediate-release and sustained-release nicotinic acid. Initial prescription amounts are 500 mg/day, increased over time until a therapeutic effect is achieved. Immediate-release doses can be as high as 3,000 mg/day; sustained-release as high as 2,000 mg/day. Despite the proven lipid changes, nicotinic acid has not been found useful for decreasing the risk of cardiovascular disease in those already prescribed a statin drug. A 2010 review had concluded that nicotinic acid was effective as a mono-therapy, but a 2017 review incorporating twice as many trials concluded that prescription nicotinic acid, while affecting lipid levels, did not reduce all-cause mortality, cardiovascular mortality, myocardial infarctions, nor fatal or non-fatal strokes. Prescription nicotinic acid was shown to cause hepatotoxicity and increase risk of type 2 diabetes. Nicotinic acid prescriptions in the United States had peaked in 2009 at 9.4 million, declining to 800 thousand by 2020. In 2023, it was the 288th most commonly prescribed medication in the US, with more than 500,000 prescriptions.\nNicotinic acid has the formula C6H5NO2 and belongs to the group of the pyridinecarboxylic acids. As the precursor for nicotinamide adenine dinucleotide and nicotinamide adenine dinucleotide phosphate, it is involved in DNA repair.\nExtra-terrestrial nicotinic acid has been found in carbonaceous chondrite meteorites and in sample-returns from the asteroids 162173 Ryugu and 101955 Bennu."}