Record Information
Version1.0
Created at2020-04-17 18:50:23 UTC
Updated at2020-12-07 19:11:16 UTC
CannabisDB IDCDB004918
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNicotinic acid
DescriptionNicotinic acid, also known as niacin or 3-carboxypyridine, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group. Nicotinic acid is a strong basic compound (based on its pKa). 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 its interaction with the enzyme purine nucleoside phosphorylase. In humans, nicotinic acid is involved in nicotinate and nicotinamide metabolism. Outside of the human body, Nicotinic acid is found, on average, in the highest concentration within a few different foods, such as beers, leavening agents, and yellowfin tuna and in a lower concentration in greater sturgeons, groundcherries, and muskmelons. Nicotinic acid has also been detected, but not quantified in, several different foods, such as chinese bayberries, pineappple sages, green vegetables, brassicas, and cupuaçus. This could make nicotinic acid a potential biomarker for the consumption of these foods. Nicotinic acid is a potentially toxic compound. Nicotinic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight123.11
Monoisotopic Molecular Weight123.032
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point236.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0kor-8900000000-7d3f033a49f5fad75f332014-09-20View Spectrum
GC-MSNicotinic acid, 1 TMS, GC-MS Spectrumsplash10-053i-0900000000-5daf0093df6c21c7279fSpectrum
GC-MSNicotinic acid, 1 TMS, GC-MS Spectrumsplash10-053i-0900000000-f38b6609b45de8c74565Spectrum
GC-MSNicotinic acid, non-derivatized, GC-MS Spectrumsplash10-0540-0900000000-4f55c81a6cd42f1b961dSpectrum
GC-MSNicotinic acid, 1 TMS, GC-MS Spectrumsplash10-057r-5900000000-00bf3662b5b9db533c0aSpectrum
GC-MSNicotinic acid, 1 TMS, GC-MS Spectrumsplash10-0569-2900000000-7820ea736b03b71d2cb8Spectrum
GC-MSNicotinic acid, non-derivatized, GC-MS Spectrumsplash10-0kmi-7900000000-9e4efda763cce5ddfe57Spectrum
GC-MSNicotinic acid, non-derivatized, GC-MS Spectrumsplash10-053i-0900000000-5daf0093df6c21c7279fSpectrum
GC-MSNicotinic acid, non-derivatized, GC-MS Spectrumsplash10-053i-0900000000-f38b6609b45de8c74565Spectrum
GC-MSNicotinic acid, non-derivatized, GC-MS Spectrumsplash10-0540-0900000000-4f55c81a6cd42f1b961dSpectrum
GC-MSNicotinic acid, non-derivatized, GC-MS Spectrumsplash10-057r-5900000000-00bf3662b5b9db533c0aSpectrum
GC-MSNicotinic acid, non-derivatized, GC-MS Spectrumsplash10-0569-2900000000-7820ea736b03b71d2cb8Spectrum
GC-MSNicotinic acid, non-derivatized, GC-MS Spectrumsplash10-0540-0900000000-a701904fe6ded0abd98fSpectrum
Predicted GC-MSNicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i0-9700000000-d7620f1dc8f42d1498b9Spectrum
Predicted GC-MSNicotinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9600000000-c3303cf4e83870b3e656Spectrum
Predicted GC-MSNicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1900000000-27508608b33f1fb9f2212012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-9100000000-a2037c9695659dceabd12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ufr-9100000000-4a2649a83ad2a40e51942012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0kmi-7900000000-1bc47d1b1850f54fb7c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-1900000000-a352c5ce16d4b682b0522012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-ab23ecb032e387b40bd92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-02e37a1cfd39470375792012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-75d7e6658d2d6eca736e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0udi-9000000000-21a2d68d4f364c596f1d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0ab9-0900000000-a74db528f61c435876c82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-6900000000-773c08ab92ace4d48a9c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00aj-9100000000-07b12fbe942e6c7fb12d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-005a-9000000000-66e0a5ba2ca8dbba1ed52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-fbf8ba47b56d7cc7be812012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-0900000000-eaf82f6ab0befde118e92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00di-0900000000-eaf82f6ab0befde118e92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9300000000-b1a48f694fba565108a12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-a352c5ce16d4b682b0522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-ab23ecb032e387b40bd92017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-25068c42378f727569222016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-6278a1e122005f48fcaf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9000000000-e4e41ed9bef32955889e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4900000000-85d44ecd8ad348eeacd12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-4911305982583ae208952016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4dea4a2d4a55907605ea2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Nicotinate-nucleotide pyrophosphorylase [carboxylating]QPRT16p11.2Q15274 details
Nicotinamide N-methyltransferaseNNMT11q23.1P40261 details
G-protein coupled receptor 109BGPR109B12q24.31P49019 details
G-protein coupled receptor 109AGPR109A12q24.31Q8TDS4 details
Purine nucleoside phosphorylasePNP14q13.1P00491 details
Nicotinate phosphoribosyltransferaseNAPRT18q24.3Q6XQN6 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Monocarboxylate transporter 1SLC16A11p12P53985 details
Solute carrier family 22 member 5SLC22A55q31O76082 details
Solute carrier organic anion transporter family member 2B1SLCO2B111q13O94956 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 2D6CYP2D622q13.1P10635 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
G-protein coupled receptor 109BGPR109B12q24.31P49019 details
G-protein coupled receptor 109AGPR109A12q24.31Q8TDS4 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001488
DrugBank IDDB00627
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001014
KNApSAcK IDC00000208
Chemspider ID913
KEGG Compound IDC00253
BioCyc IDNIACINE
BiGG ID34401
Wikipedia LinkNiacin
METLIN ID6272
PubChem Compound938
PDB IDNot Available
ChEBI ID15940
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 12 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
QPRT
Uniprot ID:
Q15274
Molecular weight:
30815.28
General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the N-methylation of nicotinamide and other pyridines to form pyridinium ions. This activity is important for biotransformation of many drugs and xenobiotic compounds.
Gene Name:
NNMT
Uniprot ID:
P40261
Molecular weight:
29573.705
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for 3-OH-octanoid acid mediates a negative feedback regulation of adipocyte lipolysis to counteract prolipolytic influences under conditions of physiological or pathological increases in beta-oxidation rates. Acts as a low affinity receptor for nicotinic acid. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet
Gene Name:
GPR109B
Uniprot ID:
P49019
Molecular weight:
44495.0
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Acts as a high affinity receptor for both nicotinic acid (also known as niacin) and (D)-beta-hydroxybutyrate and mediates increased adiponectin secretion and decreased lipolysis through G(i)-protein-mediated inhibition of adenylyl cyclase. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet. Mediates nicotinic acid-induced apoptosis in mature neutrophils. Receptor activation by nicotinic acid results in reduced cAMP levels which may affect activity of cAMP-dependent protein kinase A and phosphorylation of target proteins, leading to neutrophil apoptosis. The rank order of potency for the displacement of nicotinic acid binding is 5- methyl pyrazole-3-carboxylic acid = pyridine-3-acetic acid > acifran > 5-methyl nicotinic acid = acipimox >> nicotinuric acid = nicotinamide
Gene Name:
GPR109A
Uniprot ID:
Q8TDS4
Molecular weight:
41849.1
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69
General function:
Involved in nicotinate phosphoribosyltransferase activity
Specific function:
Catalyzes the conversion of nicotinic acid (NA) to NA mononucleotide (NaMN). Essential for NA to increase cellular NAD levels and prevent oxidative stress of the cells.
Gene Name:
NAPRT1
Uniprot ID:
Q6XQN6
Molecular weight:
57577.575

Transporters

General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular weight:
53957.7
General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular weight:
76697.9

Only showing the first 10 proteins. There are 12 proteins in total.