Showing metabocard for Nicotinic acid (BMDB0001488)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:38 UTC
Update Date2020-06-04 20:49:49 UTC
BMDB IDBMDB0001488
Secondary Accession Numbers
  • BMDB01488
Metabolite Identification
Common NameNicotinic acid
DescriptionNicotinic acid, also known as niacin or nicotinate, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Nicotinic acid is a drug which is used for the treatment of type iv and v hyperlipidemia. it is indicated as ajunctive therapy. Nicotinic acid exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Nicotinic acid exists in all living species, ranging from bacteria to humans. Nicotinic acid and ribose 1-phosphate can be biosynthesized from nicotinate D-ribonucleoside through the action of the enzyme purine nucleoside phosphorylase. In cattle, nicotinic acid is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway. Nicotinic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-CarboxypyridineChEBI
3-Pyridinecarboxylic acidChEBI
3-Pyridylcarboxylic acidChEBI
Acide nicotiniqueChEBI
Acido nicotinicoChEBI
Acidum nicotinicumChEBI
Anti-pellagra vitaminChEBI
beta-Pyridinecarboxylic acidChEBI
m-Pyridinecarboxylic acidChEBI
NiacinChEBI
NikotinsaeureChEBI
P.P. factorChEBI
Pellagra preventive factorChEBI
PP FactorChEBI
Pyridine-beta-carboxylic acidChEBI
Vitamin b3ChEBI
NiacorKegg
NiaspanKegg
3-PyridinecarboxylateGenerator
3-PyridylcarboxylateGenerator
b-PyridinecarboxylateGenerator
b-Pyridinecarboxylic acidGenerator
beta-PyridinecarboxylateGenerator
Β-pyridinecarboxylateGenerator
Β-pyridinecarboxylic acidGenerator
m-PyridinecarboxylateGenerator
Pyridine-b-carboxylateGenerator
Pyridine-b-carboxylic acidGenerator
Pyridine-beta-carboxylateGenerator
Pyridine-β-carboxylateGenerator
Pyridine-β-carboxylic acidGenerator
NicotinateGenerator
3-CarboxylpyridineHMDB
AkotinHMDB
ApelagrinHMDB
DaskilHMDB
EfacinHMDB
EnduracinHMDB
LinicHMDB
NiacHMDB
NiacineHMDB
NicacidHMDB
NicaminHMDB
NicanginHMDB
Nico-spanHMDB
NicobidHMDB
NicocapHMDB
NicodelmineHMDB
NicolarHMDB
NiconacidHMDB
Nicosan 3HMDB
NicotinipcaHMDB
NicylHMDB
NyclinHMDB
PellagrinHMDB
PeloninHMDB
Slo-niacinHMDB
WampocapHMDB
Aluminum salt, niacinHMDB
InduracinHMDB
Niacin cobalt (2+) saltHMDB
Niacin iron (2+) saltHMDB
Niacin lithium saltHMDB
Niacin magnesium saltHMDB
Niacin sodium saltHMDB
Nico-400HMDB
Potassium salt, niacinHMDB
Sodium salt, niacinHMDB
Tosylate, niacinHMDB
Nicotinate, lithiumHMDB
Hydrochloride, niacinHMDB
Niacin aluminum saltHMDB
Niacin calcium saltHMDB
Niacin copper (2+) saltHMDB
Niacin hydrochlorideHMDB
Niacin lithium salt, hemihydrateHMDB
Nico400HMDB
Tartrate, niacinHMDB
3 Pyridinecarboxylic acidHMDB
Lithium nicotinateHMDB
Niacin ammonium saltHMDB
Niacin manganese (2+) saltHMDB
Niacin potassium saltHMDB
Niacin tartrateHMDB
Niacin tosylateHMDB
Niacin zinc saltHMDB
Nico 400HMDB
Chemical FormulaC6H5NO2
Average Molecular Weight123.1094
Monoisotopic Molecular Weight123.032028409
IUPAC Namepyridine-3-carboxylic acid
Traditional Nameniacin
CAS Registry Number59-67-6
SMILES
OC(=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChI KeyPVNIIMVLHYAWGP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point236.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.0 mg/mLNot Available
LogP0.36SANGSTER (1993)
Predicted Properties
PropertyValueSource
logP0.29ALOGPS
logP-0.17ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.16 m³·mol⁻¹ChemAxon
Polarizability11.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Adipose Tissue
  • Colostrum
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Milk
  • Muscle
  • Ruminal Fluid
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.0669 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.0669 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.554 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.148 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3.493 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.123 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.311 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.554 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.204 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.392 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.635 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.635 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.529 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.311 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified6.823 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.204 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.311 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.204 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.473 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.473 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.311 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.392 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.311 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified6.498 uMNot SpecifiedNot SpecifiedNormal
    • Park, Y. W; Juáre...
 details
MilkDetected and Quantified7.229 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.229 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.473 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.0669 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.935 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified32.492 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified6.823 - 7.148 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified43 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified62.1 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified41.1 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified37.4 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified60 +/- 10 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified37.45 +/- 7.48 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified18-46 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified24.7 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified35.7 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified32.2 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified21.5 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
 details
Ruminal FluidDetected and Quantified43 +/- 11 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified62 +/- 17 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified41 +/- 12 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified37 +/- 8 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified41.1 +/- 11.8 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
 details
HMDB IDHMDB0001488
DrugBank IDDB00627
Phenol Explorer Compound IDNot Available
FooDB IDFDB001014
KNApSAcK IDC00000208
Chemspider ID913
KEGG Compound IDC00253
BioCyc IDNIACINE
BiGG ID34401
Wikipedia LinkNiacin
METLIN ID6272
PubChem Compound938
PDB IDNot Available
ChEBI ID15940
References
Synthesis ReferenceMcElvain, S. M.; Goese, M. A. Preparation of nicotinic acid from pyridine. Journal of the American Chemical Society (1941), 63 2283-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. [PubMed:17558655 ]
  2. Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S. [PubMed:22081685 ]
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  4. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
  5. USDA Food Composition Databases [Link]
  6. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

Enzyme Details
1. Diacylglycerol O-acyltransferase 2
General function:
Involved in diacylglycerol O-acyltransferase activity
Specific function:
Essential acyltransferase that catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for synthesis and storage of intracellular triglycerides. Probably plays a central role in cytosolic lipid accumulation. In liver, is primarily responsible for incorporating endogenously synthesized fatty acids into triglycerides. Functions also as an acyl-CoA retinol acyltransferase (ARAT) (By similarity).
Gene Name:
DGAT2
Uniprot ID:
Q70VZ8
Molecular weight:
40896.0