P. aeruginosa Metabolome Database: nicotinate (PAMDB110777)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110777

Identification

Name:

nicotinate

Description:

A pyridinemonocarboxylate that is the conjugate base of nicotinic acid, arising from deprotonation of the carboxy group; major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

3-pyridinecarboxylic acid
nicotinic acid
wampocap
nicolar
nicocap
nicobid
nico-400-
nicamin
niacin
niacine
vitamin B₃
3-pyridinecarboxylate
pyridine-3-carboxylate

Chemical Formula:

C₆H₄NO₂

Average Molecular Weight:

122.1

Monoisotopic Molecular Weight:

123.0320284099

InChI Key:

PVNIIMVLHYAWGP-UHFFFAOYSA-M

InChI:

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

CAS number:

59-67-6

IUPAC Name:

pyridine-3-carboxylate

Traditional IUPAC Name:

niacin

SMILES:

C1(C=CC(C([O-])=O)=CN=1)

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These 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

Charge:

-1

Melting point:

236.6 °C

Experimental Properties:

Property	Value	Reference
Melting Point	236.6 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18.0 mg/mL	Not Available
LogP	0.36	SANGSTER (1993)

Predicted Properties

Property	Value	Source
Water Solubility	83.1 mg/mL	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

Pathways:

Nicotinate and Nicotinamide Metabolism pae00760

Spectra

Spectra:

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

References

References:

Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. Physiological genomics 29, Pubmed: 17190852
Galassi L, Di Stefano M, Brunetti L, Orsomando G, Amici A, Ruggieri S, Magni G (2012)Characterization of human nicotinate phosphoribosyltransferase: Kinetic studies, structure prediction and functional analysis by site-directed mutagenesis. Biochimie 94, Pubmed: 21742010
Jeanguenin L, Lara-Núñez A, Rodionov DA, Osterman AL, Komarova NY, Rentsch D, Gregory JF, Hanson AD (2012)Comparative genomics and functional analysis of the NiaP family uncover nicotinate transporters from bacteria, plants, and mammals. Functional & integrative genomics 12, Pubmed: 21953179

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)

Links

External Links:

Resource	Link
CAS	59-67-6
ChEBI	32544
ChemSpider	912
HMDB	HMDB01488
IAF1260	34401
KEGG	C00253
MetaboLights	MTBLC32544
PubChem	937

nicotinate (PAMDB110777)

Structure for nicotinate (PAMDB110777)