Milk Composition Database: Showing metabocard for Nicotinic acid (BMDB0001488)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:46:38 UTC

Update Date

2020-06-04 20:49:49 UTC

MCDB ID

BMDB0001488

Secondary Accession Numbers

BMDB01488

Metabolite Identification

Common Name

Nicotinic acid

Description

Nicotinic 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

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	236.6 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18 mg/mL	Not Available
LogP	0.36	SANGSTER (1993)

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0569-2900000000-7820ea736b03b71d2cb8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kmi-7900000000-9e4efda763cce5ddfe57	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-053i-0900000000-5daf0093df6c21c7279f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-053i-0900000000-f38b6609b45de8c74565	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0540-0900000000-4f55c81a6cd42f1b961d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-057r-5900000000-00bf3662b5b9db533c0a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0569-2900000000-7820ea736b03b71d2cb8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0540-0900000000-a701904fe6ded0abd98f	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i0-9700000000-d7620f1dc8f42d1498b9	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9600000000-c3303cf4e83870b3e656	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-1900000000-27508608b33f1fb9f221	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-003r-9100000000-a2037c9695659dceabd1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ufr-9100000000-4a2649a83ad2a40e5194	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0kmi-7900000000-1bc47d1b1850f54fb7c2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-1900000000-a352c5ce16d4b682b052	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-ab23ecb032e387b40bd9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-02e37a1cfd3947037579	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-75d7e6658d2d6eca736e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0udi-9000000000-21a2d68d4f364c596f1d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0ab9-0900000000-a74db528f61c435876c8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-6900000000-773c08ab92ace4d48a9c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00aj-9100000000-07b12fbe942e6c7fb12d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-005a-9000000000-66e0a5ba2ca8dbba1ed5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-fbf8ba47b56d7cc7be81	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0900000000-eaf82f6ab0befde118e9	2012-08-31	View Spectrum
LC-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
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-9300000000-b1a48f694fba565108a1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-1900000000-a352c5ce16d4b682b052	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-ab23ecb032e387b40bd9	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-25068c42378f72756922	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3900000000-6278a1e122005f48fcaf	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9000000000-e4e41ed9bef32955889e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-4900000000-85d44ecd8ad348eeacd1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-4911305982583ae20895	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4dea4a2d4a55907605ea	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0kor-8900000000-7d3f033a49f5fad75f33	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View 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)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	32 uM	PMID: 17558655	details
Detected and Quantified	7.067 uM	USDA Food Co...	details
Detected and Quantified	7.067 uM	USDA Food Co...	details
Detected and Quantified	7.554 uM	USDA Food Co...	details
Detected and Quantified	7.148 uM	USDA Food Co...	details
Detected and Quantified	3.493 uM	USDA Food Co...	details
Detected and Quantified	8.123 uM	USDA Food Co...	details
Detected and Quantified	7.311 uM	USDA Food Co...	details
Detected and Quantified	7.554 uM	USDA Food Co...	details
Detected and Quantified	8.204 uM	USDA Food Co...	details
Detected and Quantified	7.392 uM	USDA Food Co...	details
Detected and Quantified	7.635 uM	USDA Food Co...	details
Detected and Quantified	7.635 uM	USDA Food Co...	details
Detected and Quantified	8.529 uM	Fooddata+, T...	details
Detected and Quantified	7.311 uM	Fooddata+, T...	details
Detected and Quantified	6.823 uM	USDA Food Co...	details
Detected and Quantified	8.204 uM	USDA Food Co...	details
Detected and Quantified	7.311 uM	USDA Food Co...	details
Detected and Quantified	8.204 uM	USDA Food Co...	details
Detected and Quantified	7.473 uM	USDA Food Co...	details
Detected and Quantified	7.473 uM	USDA Food Co...	details
Detected and Quantified	7.311 uM	Fooddata+, T...	details
Detected and Quantified	7.392 uM	Fooddata+, T...	details
Detected and Quantified	7.311 uM	Fooddata+, T...	details
Detected and Quantified	7.229 uM	USDA Food Co...	details
Detected and Quantified	7.229 uM	USDA Food Co...	details
Detected and Quantified	7.473 uM	Fooddata+, T...	details
Detected and Quantified	7.067 uM	Fooddata+, T...	details
Detected and Quantified	8.935 uM	Fooddata+, T...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	6.498 uM	Park, Y. W; Juáre...	details
Detected and Quantified	6.823 - 7.148 uM	PMID: 22081685	details

External Links

HMDB ID

HMDB0001488

DrugBank ID

DB00627

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15940

References

Synthesis Reference

McElvain, 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)

Download (PDF)

General References

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 ]
Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S. [PubMed:22081685 ]
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.
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.
USDA Food Composition Databases [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Nicotinic acid (BMDB0001488)

Structure for BMDB0001488 (Nicotinic acid)