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59-67-6 molecular structure
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pyridine-3-carboxylic acid

ChemBase ID: 509
Molecular Formular: C6H5NO2
Molecular Mass: 123.1094
Monoisotopic Mass: 123.03202841
SMILES and InChIs

SMILES:
OC(=O)c1cccnc1
Canonical SMILES:
OC(=O)c1cccnc1
InChI:
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChIKey:
PVNIIMVLHYAWGP-UHFFFAOYSA-N

Cite this record

CBID:509 http://www.chembase.cn/molecule-509.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
pyridine-3-carboxylic acid
IUPAC Systematic name
Pyridine-3-carboxylic acid
IUPAC Traditional name
niacin
Brand Name
Akotin
Anti-Pellagra Vitamin
Apelagrin
Bionic
Daskil
Davitamon PP
Diacin
Direktan
Efacin
Kyselina Nikotinova
Linic
NICO
Naotin
Niac
Nicacid
Nicangin
Nico-Span
Nicocidin
Nicocrisina
Nicodan
Nicodelmine
Nicodon
Niconacid
Niconat
Niconazid
Nicorol
Nicosan 3
Nicoside
Nicosyl
Nicotamin
Nicotene
Nicotil
Nicotinipca
Nicotinsaure
Nicovasan
Nicovasen
Nicovel
Nicyl
Nipellen
Nyclin
P.P. Factor
Pellagra Preventive Factor
Pellagramin
Pellagrin
Pelonin
Peviton
PP Factor
Sk-Niacin
Tega-Span
Tinic
Vitaplex N
Niaspan
Simcor
Synonyms
Acide Nicotinique
Acidum Nicotinicum
M-Pyridinecarboxylic Acid
NAH
Nicotine Acid
Nicotinic Acid
Pyridinecarboxylic Acid
Pyridylcarboxylic Acid
Vitamin B3
3-Pyridinecarboxylic acid
niacin
Niacin
Niacinamide
Niacin(Nicotinic acid)
Pyridine-3-carboxylic acid
3-Carboxypyridine
Nicotinic acid
Pellagra preventive factor
3-Carboxylpyridine
Akotin
Apelagrin
Niacor
Niaspan
Nicacid
Pelonin
Vitamin B5
Wampocap
β-Pyridinecarboxylic Acid
Bionic
Nicotinic acid
NICOTINIC ACID FREE ACID
3-Picolinic acid
Vitamin B3
尼可丁酸
3-吡啶甲酸
吡啶-3-羧酸
尼亚生
抗糙皮病因子
维生素 B3
烟酸
CAS Number
59-67-6
EC Number
200-441-0
MDL Number
MFCD00006391
Beilstein Number
109591
Merck Index
146525
PubChem SID
24886385
46507508
160963972
24886386
24897734
24897668
24897445
24897443
24886384
24871534
PubChem CID
938
CHEBI ID
15940
ATC CODE
C04AC01
C10AD02
CHEMBL
573
Chemspider ID
913
DrugBank ID
DB00627
Gmelin ID
3340
IUPHAR ligand ID
1588
KEGG ID
D00049
MeSH Name
Niacin
Unique Ingredient Identifier
2679MF687A
Wikipedia Title
Niacin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.7856104  H Acceptors
H Donor LogD (pH = 5.5) -1.3303725 
LogD (pH = 7.4) -2.8627489  Log P -0.16644564 
Molar Refractivity 31.1573 cm3 Polarizability 11.793079 Å3
Polar Surface Area 50.19 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.29  LOG S -0.17 
Solubility (Water) 8.31e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
18 g L-1 in water expand Show data source
18 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
White Solid expand Show data source
White, translucent crystals expand Show data source
Melting Point
189-202°C expand Show data source
233-238 °C expand Show data source
234-238 °C expand Show data source
234-238 °C (dec.) expand Show data source
236.6 expand Show data source
236.85°C (510K) expand Show data source
236-239 °C(lit.) expand Show data source
236-239(subl.)°C expand Show data source
236-239°C expand Show data source
Flash Point
193 °C expand Show data source
193°C expand Show data source
293°C(559°F) expand Show data source
379.4 °F expand Show data source
Auto Ignition Point
365 °C expand Show data source
Density
1.4 expand Show data source
1.467 expand Show data source
1.473 g cm-3 expand Show data source
Refractive Index
1.4936 expand Show data source
Vapor Pressure
5.7 x 10-6 mm Hg at 25 °C (estimated) expand Show data source
Partition Coefficient
0.219 expand Show data source
Hydrophobicity(logP)
0.4 expand Show data source
pKa
2.201 expand Show data source
pKb
11.796 expand Show data source
Isoelectric Point
4.75 expand Show data source
Dipole Moment
0.1271305813 D expand Show data source
Std enthalpy of combustion
-2.73083 MJ mol-1 expand Show data source
Std enthalpy of formation
-344.9 kJ mol-1 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
Irritant/Light Sensitive/Store under Argon expand Show data source
RTECS
QT0525000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
36 expand Show data source
R36/37/38 expand Show data source
Safety Statements
26 expand Show data source
S26, S36 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
NFPA704
NFPA 704 diagram
1
1
0
expand Show data source
GHS Hazard statements
H319 expand Show data source
GHS Precautionary statements
P280-P264-P305+P351+P338-P337+P313 expand Show data source
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Admin Routes
Intramuscular, Oral expand Show data source
Half Life
20-45 min expand Show data source
Gene Information
human ... CYP1A2(1544)rat ... Chrnb2(54239) expand Show data source
Purity
≥99% expand Show data source
≥98% expand Show data source
≥99.0% (HPLC) expand Show data source
≥99.5% expand Show data source
≥99.5% (HPLC) expand Show data source
97% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
analytical standard expand Show data source
matrix substance for MALDI-MS expand Show data source
Ph Eur expand Show data source
purum expand Show data source
SAJ special grade expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Packaging
ampule of 1000 mg expand Show data source
Suitability
meets USP testing specifications expand Show data source
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
suitable for insect cell culture expand Show data source
suitable for plant cell culture expand Show data source
Ignition Residue
<0.05% expand Show data source
≤0.05% expand Show data source
Impurities
≤0.2% water expand Show data source
Cation Traces
Ba: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Loss on Drying
≤0.2% loss on drying expand Show data source
Quality Level
PREMIUM expand Show data source
Feature
standard type water soluble vitamin expand Show data source
Analyte suitability
oligonucleotides expand Show data source
peptides expand Show data source
proteins expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia expand Show data source
Empirical Formula (Hill Notation)
C6H5NO2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02194716 external link
Cell Culture Reagent
Purity: 99+%
Crystalline
Free Acid
MP Biomedicals - 02102446 external link
Purity: 99+%
Crystalline
Free Acid
DrugBank - DB00627 external link
Item Information
Drug Groups approved; nutraceutical; investigational
Description A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has pellagra-curative, vasodilating, and antilipemic properties. [PubChem]
Indication For the treatment of type IV and V hyperlipidemia. It is indicated as ajunctive therapy.
Pharmacology Niacin and niacinamide are indicated for prevention and treatment of vitamin B3 deficiency states. Vitamin B3 (Niacin) also acts to reduce LDL cholesterol, triglycerides, and HDL cholesterol. The magnitude of individual lipid and lipoprotein responses may be influenced by the severity and type of underlying lipid abnormality. The increase in total HDL is associated with a shift in the distribution of HDL subfractions (as defined by ultra-centrifugation) with an increase in the HDL2:HDL3 ratio and an increase in apolipoprotein A-I content. Vitamin B3 (Niacin) treatment also decreases the serum levels of apolipoprotein B-100 (apo B), the major protein component of the VLDL (very low-density lipoprotein) and LDL fractions, and of lipoprotein-a, a variant form of LDL independently associated with coronary risk.
Toxicity Nicotinic acid can cause vasodilation of cutaneous blood vessels resulting in increased blood flow, principally in the face, neck and chest. This produces the niacin- or nicotinic acid-flush. The niacin-flush is thought to be mediated via the prostaglandin prostacyclin. Histamine may also play a role in the niacin-flush. Flushing is the adverse reaction first observed after intake of a large dose of nicotinic acid, and the most bothersome one. LD50 7000 mg/kg (Rat)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Both nicotinic acid and nicotinamide are efficiently absorbed from the stomach and small intestine.
Half Life 20-45 minutes.
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1744 external link
Research Area: Metabolic Disease
Biological Activity:
Niacin(Nicotinic acid) is a water-soluble vitamin belonging to the vitamin B family, which occurs in many animal and plant tissues, with antihyperlipidemic activity. Niacin is converted to its active form niacinamide, which is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and its phosphate form, NADP. These coenzymes play an important role in tissue respiration and in glycogen, lipid, amino acid, protein, and purine metabolism. [1, 2]
Sigma Aldrich - 72309 external link
Other Notes
Coenzyme and Cofactors, vol 2: Pyridine Nucleotide Coenzymes1,2
Sigma Aldrich - N4126 external link
Biochem/physiol Actions
降低肝脏极低密度脂蛋白和载脂蛋白 B 的产量。
包装
1 kg in poly bottle
5, 100, 500 g in poly bottle
Toronto Research Chemicals - N429250 external link
Nicotinic acid. It is a precursor of the coenzymes NAD and NADP. Widely distributed in nature; appreciable amounts are found in liver , fish, yeast and cereal grains. Dietary deficiency is associated with pellagra. The term “niacin” has also been applied

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://www.cancer.gov/drugdictionary/?CdrID=38351
  • •  http://en.wikipedia.org/wiki/Niacin
  • • Darby, W.J., et al.: Nutr. Rev., 33, 289 (1975)
  • • Black, A., et al.: Eur. J. Clin. Nutr., 54, 395 (1975)
  • • Cole, T., et al.: Br. Med. J., 320, 1240 (1975)
  • • Forshee, R., et al.: J. Nutr., 134, 2733 (1975)
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PATENTS

PATENTS

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INTERNET

INTERNET

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