Showing Compound Nicotinic acid (FDB001014)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:48 UTC

Update date

2020-09-17 15:38:56 UTC

Primary ID

FDB001014

Secondary Accession Numbers

FDB003781
FDB031056

Chemical Information

FooDB Name

Nicotinic acid

Description

Nicotinic 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.

CAS Number

59-67-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3 Pyridinecarboxylic acid	HMDB
3-Carboxylpyridine	HMDB
3-Carboxypyridine	ChEBI
3-Pyridinecarboxylate	Generator
3-Pyridinecarboxylic acid	ChEBI
3-Pyridylcarboxylate	Generator
3-Pyridylcarboxylic acid	ChEBI
Acide nicotinique	ChEBI
Acido nicotinico	ChEBI
Acidum nicotinicum	ChEBI

Showing 1 to 10 of 101 entries

Predicted Properties

Property	Value	Source
Water Solubility	83.1 g/L	ALOGPS
logP	0.29	ALOGPS
logP	-0.17	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	4.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.16 m³·mol⁻¹	ChemAxon
Polarizability	11.3 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H5NO2

IUPAC name

pyridine-3-carboxylic acid

InChI Identifier

InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)

InChI Key

PVNIIMVLHYAWGP-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1=CN=CC=C1

Average Molecular Weight

123.1094

Monoisotopic Molecular Weight

123.032028409

Classification

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridine alkaloid (CHEBI:15940 )
pyridinemonocarboxylic acid (CHEBI:15940 )
Water-soluble vitamins (C00253 )
Pyridine alkaloids (C00253 )

Ontology

Metabolism and nutrition disorders:

Hyperglycemia

Eye disorders:

Blurred vision

Disposition

Route of exposure:

Enteral:

Ingestion

Parenteral:

Intramuscular

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Alcoholism

Role

Industrial application:

Pharmaceutical industry:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	0.36	SANGSTER (1993)
Experimental pKa	pKa2 4.82 (25°)	DFC
Experimental Water Solubility	18 mg/mL at 20 oC	YALKOWSKY,SH & HE,Y (2003)
Isoelectric point	Not Available
Mass Composition	C 58.54%; H 4.09%; N 11.38%; O 25.99%	DFC
Melting Point	Mp 236° (225-227°)	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0kor-8900000000-7d3f033a49f5fad75f33	2014-09-20	View Spectrum
GC-MS	Nicotinic acid, 1 TMS, GC-MS Spectrum	splash10-053i-0900000000-5daf0093df6c21c7279f	Spectrum
GC-MS	Nicotinic acid, 1 TMS, GC-MS Spectrum	splash10-053i-0900000000-f38b6609b45de8c74565	Spectrum
GC-MS	Nicotinic acid, non-derivatized, GC-MS Spectrum	splash10-0540-0900000000-4f55c81a6cd42f1b961d	Spectrum
GC-MS	Nicotinic acid, 1 TMS, GC-MS Spectrum	splash10-057r-5900000000-00bf3662b5b9db533c0a	Spectrum
GC-MS	Nicotinic acid, 1 TMS, GC-MS Spectrum	splash10-0569-2900000000-7820ea736b03b71d2cb8	Spectrum
GC-MS	Nicotinic acid, non-derivatized, GC-MS Spectrum	splash10-0kmi-7900000000-9e4efda763cce5ddfe57	Spectrum
GC-MS	Nicotinic acid, non-derivatized, GC-MS Spectrum	splash10-053i-0900000000-5daf0093df6c21c7279f	Spectrum
GC-MS	Nicotinic acid, non-derivatized, GC-MS Spectrum	splash10-053i-0900000000-f38b6609b45de8c74565	Spectrum
GC-MS	Nicotinic acid, non-derivatized, GC-MS Spectrum	splash10-0540-0900000000-4f55c81a6cd42f1b961d	Spectrum
GC-MS	Nicotinic acid, non-derivatized, GC-MS Spectrum	splash10-057r-5900000000-00bf3662b5b9db533c0a	Spectrum
GC-MS	Nicotinic acid, non-derivatized, GC-MS Spectrum	splash10-0569-2900000000-7820ea736b03b71d2cb8	Spectrum
GC-MS	Nicotinic acid, non-derivatized, GC-MS Spectrum	splash10-0540-0900000000-a701904fe6ded0abd98f	Spectrum
Predicted GC-MS	Nicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05i0-9700000000-d7620f1dc8f42d1498b9	Spectrum
Predicted GC-MS	Nicotinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-9600000000-c3303cf4e83870b3e656	Spectrum
Predicted GC-MS	Nicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Nicotinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-1900000000-27508608b33f1fb9f221	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-003r-9100000000-a2037c9695659dceabd1	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ufr-9100000000-4a2649a83ad2a40e5194	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0kmi-7900000000-1bc47d1b1850f54fb7c2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-1900000000-a352c5ce16d4b682b052	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-ab23ecb032e387b40bd9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-02e37a1cfd3947037579	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-75d7e6658d2d6eca736e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0udi-9000000000-21a2d68d4f364c596f1d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0ab9-0900000000-a74db528f61c435876c8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-6900000000-773c08ab92ace4d48a9c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00aj-9100000000-07b12fbe942e6c7fb12d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-005a-9000000000-66e0a5ba2ca8dbba1ed5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-fbf8ba47b56d7cc7be81	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0900000000-eaf82f6ab0befde118e9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00di-0900000000-eaf82f6ab0befde118e9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-9300000000-b1a48f694fba565108a1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-1900000000-a352c5ce16d4b682b052	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-ab23ecb032e387b40bd9	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-25068c42378f72756922	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3900000000-6278a1e122005f48fcaf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9000000000-e4e41ed9bef32955889e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-4900000000-85d44ecd8ad348eeacd1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-4911305982583ae20895	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4dea4a2d4a55907605ea	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H 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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15940

Phenol-Explorer ID

Not Available

DrugBank ID

DB00627

HMDB ID

HMDB01488

CRC / DFC (Dictionary of Food Compounds) ID

BPB04-S:BPB04-S

EAFUS ID

2661

Dr. Duke ID

NICOTINIC-ACID|NIACIN

BIGG ID

34401

KNApSAcK ID

C00000208

HET ID

NIO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Niacin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti acrodynic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti amblyopic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti anginal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cataract	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti chilblain			DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti Crohn's	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE