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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:46 UTC
Update Date2023-02-21 17:16:34 UTC
HMDB IDHMDB0003269
Secondary Accession Numbers
  • HMDB03269
Metabolite Identification
Common NameNicotinuric acid
DescriptionNicotinuric acid is an acylglycine. Acylglycines are normally minor metabolites of fatty acids. However, the excretion of certain acylglycines is increased in several inborn errors of metabolism. In certain cases, the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acylglycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction acyl-CoA + glycine <-> CoA + N-acylglycine. Nicotinuric acid is the major detoxification product of nicotinic acid. It may serve as a simple quantitative index of hepatic biotransformation of nicotinic acid (PMID:3243933 ).
Structure
Thumb
Synonyms
ValueSource
N-(Pyridin-3-ylcarbonyl)glycineChEBI
N-NicotinylglycineChEBI
NicotinoylglycineChEBI
NicotinurateChEBI
NicotinylglycineChEBI
NicotinateGenerator
Nicotinic acidGenerator
N-(3-Pyridinylcarbonyl)-(9ci)-glycineHMDB
N-(3-Pyridinylcarbonyl)-glycineHMDB
N-Nicotinoyl-(8ci)-glycineHMDB
N-Nicotinoyl-glycineHMDB
N-NicotinurateHMDB
N-Nicotinuric acidHMDB
Nicotinoyl-glycineHMDB
Nicotinuric acid, monosodium saltHMDB
Nicotinuric acidChEBI
Chemical FormulaC8H8N2O3
Average Molecular Weight180.1607
Monoisotopic Molecular Weight180.053492132
IUPAC Name2-[(pyridin-3-yl)formamido]acetic acid
Traditional Namenicotinuric acid
CAS Registry Number583-08-4
SMILES
OC(=O)CNC(=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C8H8N2O3/c11-7(12)5-10-8(13)6-2-1-3-9-4-6/h1-4H,5H2,(H,10,13)(H,11,12)
InChI KeyZBSGKPYXQINNGF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Nicotinamide
  • Pyridine
  • Heteroaromatic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg138.07530932474
[M+H]+MetCCS_train_pos143.60830932474
[M-H]-Not Available138.075http://allccs.zhulab.cn/database/detail?ID=AllCCS00000055
[M+H]+Not Available144.146http://allccs.zhulab.cn/database/detail?ID=AllCCS00000055
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.00 +/- 1.67 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.33 (0.00 - 8.33) uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (24-38years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023135
KNApSAcK IDNot Available
Chemspider ID61774
KEGG Compound IDC05380
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNiacin
METLIN ID1499
PubChem Compound68499
PDB IDNot Available
ChEBI ID7563
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hengen N, Seiberth V, Hengen M: High-performance liquid-chromatographic determination of free nicotinic acid and its metabolite, nicotinuric acid, in plasma and urine. Clin Chem. 1978 Oct;24(10):1740-3. [PubMed:699281 ]
  2. Miyauchi Y, Sano N, Nakamura T: Simultaneous determination of nicotinic acid and its two metabolites in human plasma using solid-phase extraction in combination with high performance liquid chromatography. Int J Vitam Nutr Res. 1993;63(2):145-9. [PubMed:8407165 ]
  3. Neuvonen PJ, Roivas L, Laine K, Sundholm O: The bioavailability of sustained release nicotinic acid formulations. Br J Clin Pharmacol. 1991 Oct;32(4):473-6. [PubMed:1958442 ]
  4. Figge HL, Figge J, Souney PF, Sacks FM, Shargel L, Janosik JE, Kaul AF: Comparison of excretion of nicotinuric acid after ingestion of two controlled release nicotinic acid preparations in man. J Clin Pharmacol. 1988 Dec;28(12):1136-40. [PubMed:3243933 ]
  5. Dieterle F, Ross A, Schlotterbeck G, Senn H: Metabolite projection analysis for fast identification of metabolites in metabonomics. Application in an amiodarone study. Anal Chem. 2006 Jun 1;78(11):3551-61. [PubMed:16737207 ]
  6. Pfuhl P, Karcher U, Haring N, Baumeister A, Tawab MA, Schubert-Zsilavecz M: Simultaneous determination of niacin, niacinamide and nicotinuric acid in human plasma. J Pharm Biomed Anal. 2005 Jan 4;36(5):1045-52. [PubMed:15620531 ]

Enzymes

General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:
GLYATL3
Uniprot ID:
Q5SZD4
Molecular weight:
32703.3