Livestock Metabolome Database: Showing metabocard for Nicotinic acid (LMDB00337)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:36 UTC

Update Date

2016-07-20 20:53:04 UTC

Lmdb

LMDB00337

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nicotinic acid

Description

Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan (see below), but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Carboxypyridine	ChEBI
3-Pyridinecarboxylic acid	ChEBI
3-Pyridylcarboxylic acid	ChEBI
Acide nicotinique	ChEBI
Acido nicotinico	ChEBI
Acidum nicotinicum	ChEBI
Anti-pellagra vitamin	ChEBI
beta-Pyridinecarboxylic acid	ChEBI
m-Pyridinecarboxylic acid	ChEBI
Niacin	ChEBI
Nikotinsaeure	ChEBI
P.P. factor	ChEBI
Pellagra preventive factor	ChEBI
PP Factor	ChEBI
Pyridine-beta-carboxylic acid	ChEBI
Vitamin b3	ChEBI
Niacor	Kegg
Niaspan	Kegg
3-Pyridinecarboxylate	Generator
3-Pyridylcarboxylate	Generator
b-Pyridinecarboxylate	Generator
b-Pyridinecarboxylic acid	Generator
beta-Pyridinecarboxylate	Generator
Β-pyridinecarboxylate	Generator
Β-pyridinecarboxylic acid	Generator
m-Pyridinecarboxylate	Generator
Pyridine-b-carboxylate	Generator
Pyridine-b-carboxylic acid	Generator
Pyridine-beta-carboxylate	Generator
Pyridine-β-carboxylate	Generator
Pyridine-β-carboxylic acid	Generator
Nicotinate	Generator
3-Carboxylpyridine	HMDB
Akotin	HMDB
Apelagrin	HMDB
Daskil	HMDB
Efacin	HMDB
Enduracin	HMDB
Linic	HMDB
Niac	HMDB
Niacine	HMDB
Nicacid	HMDB
Nicamin	HMDB
Nicangin	HMDB
Nico-span	HMDB
Nicobid	HMDB
Nicocap	HMDB
Nicodelmine	HMDB
Nicolar	HMDB
Niconacid	HMDB
Nicosan 3	HMDB
Nicotinipca	HMDB
Nicyl	HMDB
Nyclin	HMDB
Pellagrin	HMDB
Pelonin	HMDB
Slo-niacin	HMDB
Wampocap	HMDB
Aluminum salt, niacin	HMDB
Induracin	HMDB
Niacin cobalt (2+) salt	HMDB
Niacin iron (2+) salt	HMDB
Niacin lithium salt	HMDB
Niacin magnesium salt	HMDB
Niacin sodium salt	HMDB
Nico-400	HMDB
Potassium salt, niacin	HMDB
Sodium salt, niacin	HMDB
Tosylate, niacin	HMDB
Nicotinate, lithium	HMDB
Hydrochloride, niacin	HMDB
Niacin aluminum salt	HMDB
Niacin calcium salt	HMDB
Niacin copper (2+) salt	HMDB
Niacin hydrochloride	HMDB
Niacin lithium salt, hemihydrate	HMDB
Nico400	HMDB
Tartrate, niacin	HMDB
3 Pyridinecarboxylic acid	HMDB
Lithium nicotinate	HMDB
Niacin ammonium salt	HMDB
Niacin manganese (2+) salt	HMDB
Niacin potassium salt	HMDB
Niacin tartrate	HMDB
Niacin tosylate	HMDB
Niacin zinc salt	HMDB
Nico 400	HMDB

Chemical Formula

C₆H₅NO₂

Average Molecular Weight

123.1094

Monoisotopic Molecular Weight

123.032028409

IUPAC Name

pyridine-3-carboxylic acid

Traditional Name

niacin

CAS Registry Number

59-67-6

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 Key

PVNIIMVLHYAWGP-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.

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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-053i-0900000000-5daf0093df6c21c7279f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-053i-0900000000-f38b6609b45de8c74565	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0540-0900000000-4f55c81a6cd42f1b961d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-057r-5900000000-00bf3662b5b9db533c0a	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0569-2900000000-7820ea736b03b71d2cb8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kmi-7900000000-9e4efda763cce5ddfe57	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-053i-0900000000-5daf0093df6c21c7279f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-053i-0900000000-f38b6609b45de8c74565	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0540-0900000000-4f55c81a6cd42f1b961d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-057r-5900000000-00bf3662b5b9db533c0a	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0569-2900000000-7820ea736b03b71d2cb8	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0540-0900000000-a701904fe6ded0abd98f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i0-9700000000-d7620f1dc8f42d1498b9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9600000000-c3303cf4e83870b3e656	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-1900000000-27508608b33f1fb9f221	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-003r-9100000000-a2037c9695659dceabd1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ufr-9100000000-4a2649a83ad2a40e5194	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0kmi-7900000000-1bc47d1b1850f54fb7c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-1900000000-a352c5ce16d4b682b052	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-ab23ecb032e387b40bd9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-02e37a1cfd3947037579	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-75d7e6658d2d6eca736e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0udi-9000000000-21a2d68d4f364c596f1d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0ab9-0900000000-a74db528f61c435876c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-6900000000-773c08ab92ace4d48a9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00aj-9100000000-07b12fbe942e6c7fb12d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-005a-9000000000-66e0a5ba2ca8dbba1ed5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-fbf8ba47b56d7cc7be81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0900000000-eaf82f6ab0befde118e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00di-0900000000-eaf82f6ab0befde118e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-9300000000-b1a48f694fba565108a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-1900000000-a352c5ce16d4b682b052	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-ab23ecb032e387b40bd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-25068c42378f72756922	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3900000000-6278a1e122005f48fcaf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9000000000-e4e41ed9bef32955889e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-4900000000-85d44ecd8ad348eeacd1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-4911305982583ae20895	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4dea4a2d4a55907605ea	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0kor-8900000000-7d3f033a49f5fad75f33	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Feces
Meat
Milk
Plasma
Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Milk	Detected and Quantified	0.8 mg/kg	Not Available	Bovine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	4.16 mg/kg	Not Available	Ovine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	2.7 mg/kg	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Ruminal Fluid	Detected and Quantified	21.5 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	24.7 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	32.2 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	35.7 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	37.4 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	41.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	43 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	62.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Ruminal Fluid	Detected and Quantified	24 +/- 13 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	37 +/- 8 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	37 +/- 8 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	41 +/- 12 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	43 +/- 11 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	62 +/- 17 uM	Not Available	Bovine	Saleem F, Bouatra...	details