Milk Composition Database: Showing metabocard for Niacinamide (BMDB0001406)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:45:29 UTC

Update Date

2020-06-04 20:55:32 UTC

MCDB ID

BMDB0001406

Secondary Accession Numbers

BMDB01406

Metabolite Identification

Common Name

Niacinamide

Description

Niacinamide, also known as nicotinamid or vitamin B3, belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Niacinamide exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Niacinamide exists in all living species, ranging from bacteria to humans. Niacinamide participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylmethionine and niacinamide can be converted into S-adenosylhomocysteine and 1-methylnicotinamide through the action of the enzyme nicotinamide N-methyltransferase. In addition, Niacinamide and ribose-1-arsenate can be converted into nicotinamide riboside and phosphoric acid through its interaction with the enzyme purine nucleoside phosphorylase. In cattle, niacinamide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway. Niacinamide is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Pyridinecarboxamide	ChEBI
beta-Pyridinecarboxamide	ChEBI
Niacin	ChEBI
Nicotinamid	ChEBI
Nicotinic acid amide	ChEBI
Nicotinsaeureamid	ChEBI
Nikotinamid	ChEBI
Nikotinsaeureamid	ChEBI
Vitamin b3	ChEBI
Vitamin PP	ChEBI
Nicotinamide	Kegg
b-Pyridinecarboxamide	Generator
Β-pyridinecarboxamide	Generator
Nicotinate amide	Generator
3-Carbamoylpyridine	HMDB
3-Pyridinecarboxylic acid amide	HMDB
Acid amide	HMDB
Amid kyseliny nikotinove	HMDB
Amide PP	HMDB
Aminicotin	HMDB
Amixicotyn	HMDB
Amnicotin	HMDB
Austrovit PP	HMDB
Benicot	HMDB
Delonin amide	HMDB
Dipegyl	HMDB
Dipigyl	HMDB
Endobion	HMDB
Factor PP	HMDB
Hansamid	HMDB
Inovitan PP	HMDB
m-(Aminocarbonyl)pyridine	HMDB
Mediatric	HMDB
NAM	HMDB
Nandervit-N	HMDB
Niacevit	HMDB
Niamide	HMDB
Niavit PP	HMDB
Nicamide	HMDB
Nicamina	HMDB
Nicamindon	HMDB
Nicasir	HMDB
Nicobion	HMDB
Nicofort	HMDB
Nicogen	HMDB
Nicomidol	HMDB
Nicosan 2	HMDB
Nicosylamide	HMDB
Nicota	HMDB
Nicotamide	HMDB
Nicotilamide	HMDB
Nicotililamido	HMDB
Nicotinamida	HMDB
Nicotinamidum	HMDB
Nicotine acid amide	HMDB
Nicotine amide	HMDB
Nicotinic amide	HMDB
Nicotinsaureamid	HMDB
Nicotol	HMDB
Nicotylamide	HMDB
Nicotylamidum	HMDB
Nicovel	HMDB
Nicovit	HMDB
Nicovitina	HMDB
Nicovitol	HMDB
Nicozymin	HMDB
Nictoamide	HMDB
Niko-tamin	HMDB
Niocinamide	HMDB
Niozymin	HMDB
Papulex	HMDB
Pelmin	HMDB
Pelmine	HMDB
Pelonin amide	HMDB
PP-Faktor	HMDB
Propamine a	HMDB
Pyridine-3-carboxylic acid amide	HMDB
Savacotyl	HMDB
Vi-nicotyl	HMDB
Vi-noctyl	HMDB
Witamina PP	HMDB
3 Pyridinecarboxamide	HMDB
Astra brand OF niacinamide	HMDB
b 3, Vitamin	HMDB
Niacinamide merck brand	HMDB
Pharmagenix brand OF niacinamide	HMDB
b3, Vitamin	HMDB
Enduramide	HMDB
Jenapharm, nicotinsäureamid	HMDB
Niacinamide jenapharm brand	HMDB
Niacinamide pharmagenix brand	HMDB
Jenapharm brand OF niacinamide	HMDB
Nicotinsäureamid jenapharm	HMDB
Vitamin b 3	HMDB
Merck brand OF niacinamide	HMDB
Niacinamide astra brand	HMDB
Niacinamide	ChEBI

Chemical Formula

C₆H₆N₂O

Average Molecular Weight

122.1246

Monoisotopic Molecular Weight

122.048012824

IUPAC Name

pyridine-3-carboxamide

Traditional Name

nicotinamide

CAS Registry Number

98-92-0

SMILES

NC(=O)C1=CC=CN=C1

InChI Identifier

InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)

InChI Key

DFPAKSUCGFBDDF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Nicotinamides

Alternative Parents

Substituents

Nicotinamide
Heteroaromatic compound
Primary carboxylic acid amide
Carboxamide group
Azacycle
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:17154 )
pyridinecarboxamide (CHEBI:17154 )
Water-soluble vitamins (C00153 )
Pyridine alkaloids (C00153 )
a vitamin (NIACINAMIDE )
an aliphatic amide (NIACINAMIDE )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	130 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	500 mg/mL at 25 °C	Not Available
LogP	-0.37	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.45	ALOGPS
logP	-0.39	ChemAxon
logS	-0.39	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	3.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.98 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.98 m³·mol⁻¹	ChemAxon
Polarizability	11.71 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)	splash10-004i-0900000000-acb6a21304b0c09c8472	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)	splash10-004r-0900000000-ce86dcff0153b66dd538	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)	splash10-004i-9500000000-790385e574240b8d39de	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-2910000000-d760b65bb76d6464038e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-4900000000-47c6f72d1bb5465c1376	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kor-9800000000-1809e537780b814af0c9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0kor-9800000000-c4a5ff5285417499eff8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-0e84a60cc2a2d44704f4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-acb6a21304b0c09c8472	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004r-0900000000-ce86dcff0153b66dd538	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-9500000000-790385e574240b8d39de	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-2910000000-d760b65bb76d6464038e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-4900000000-47c6f72d1bb5465c1376	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-0900000000-23a567506bfbc259e77c	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-8900000000-931c139355be3ef594f2	2016-09-22	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-2900000000-72a7c92eb2667f5b6c3f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-6486d230a4a2fd4bab0e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-6486d230a4a2fd4bab0e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0kor-9800000000-89d56b6cb7e033699d24	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-eed71abbb10ba926c13d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-3900000000-0c62aa6aba6e23b6c195	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9100000000-4357a8833611d1756c59	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-c9685717817d0081fe6d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0fc0-9000000000-ec0ccca306f38cf72a78	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-f6d71a6c467f84ddd6ab	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9100000000-62c4bd312efbfa37d1a1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-05714b528dc84942b9db	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9100000000-edb6a77c0dfdcbdacc5d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0900000000-eed71abbb10ba926c13d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-3900000000-0c62aa6aba6e23b6c195	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9100000000-4357a8833611d1756c59	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-c9685717817d0081fe6d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0fc0-9000000000-ec0ccca306f38cf72a78	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0900000000-960acce7ead55399b5db	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-2c7ec333d35eb740520a	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-9600000000-466f98885e2efba73575	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9200000000-6ef8d7e5edcdd0b02758	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-f38177aa475e58941088	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-9800000000-6a883d82fcd7c450f6ce	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-882d0c59d946a5087b9f	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0kor-9600000000-2b1c5667d92bc1b80b36	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	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, 25.16 MHz, D₂O, 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	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	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 but not Quantified	Not Applicable	PMID: 23438684	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	5.7 +/- 0.7 uM	PMID: 30994344	details
Detected and Quantified	5.4 +/- 0.4 uM	PMID: 30994344	details
Detected and Quantified	5 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	7 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	10.6 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	10.4 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	11.3 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	10.3 +/- 0.3 uM	PMID: 30994344	details
Detected and Quantified	5.6 +/- 2.5 uM	Superfoodly	details
Detected and Quantified	5.2 +/- 3.4 uM	Superfoodly	details
Detected and Quantified	7 +/- 2 uM	PMID: 27052539	details

External Links

HMDB ID

HMDB0001406

DrugBank ID

DB02701

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

17154

References

Synthesis Reference

Galat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945.

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 ]
Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Trammell SA, Yu L, Redpath P, Migaud ME, Brenner C: Nicotinamide Riboside Is a Major NAD+ Precursor Vitamin in Cow Milk. J Nutr. 2016 May;146(5):957-63. doi: 10.3945/jn.116.230078. Epub 2016 Apr 6. [PubMed:27052539 ]
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.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
Superfoodly [Link]

Showing metabocard for Niacinamide (BMDB0001406)

Structure for BMDB0001406 (Niacinamide)