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Record Information
Version3.6
Creation Date2006-05-22 15:12:46 UTC
Update Date2016-02-11 01:06:09 UTC
HMDB IDHMDB03269
Secondary Accession NumbersNone
Metabolite Identification
Common NameNicotinuric acid
DescriptionNicotinuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines 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. Acyl glycines 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
Nicotinuric acidChEBI
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
Chemical FormulaC8H8N2O3
Average Molecular Weight180.1607
Monoisotopic Molecular Weight180.053492132
IUPAC Name2-(pyridin-3-ylformamido)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 KeyInChIKey=ZBSGKPYXQINNGF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These 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
  • Pyridine carboxylic acid or derivatives
  • Nicotinamide
  • Pyridine
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.49 mg/mLALOGPS
logP-0.23ALOGPS
logP-1.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.94ChemAxon
pKa (Strongest Basic)3.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.29 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.96 m3·mol-1ChemAxon
Polarizability16.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-3950000000-4ea0184fb844e85c5f60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001r-0900000000-28e9d6d719938b6ef2a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0550-4900000000-4b12baba3c8ed421aab4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-ca65b11ed6964f642d97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-7691658645b49efa1218View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-1900000000-90da23067cff9198189dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9400000000-b6fb3beff4d893a45c9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-2e3fc586dec1a239f580View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-2e3ff3323d46a1520f5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-053af4d9ef684962e67bView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023135
KNApSAcK IDNot Available
Chemspider ID61774
KEGG Compound IDC05380
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03269
Metagene LinkHMDB03269
METLIN ID1499
PubChem Compound68499
PDB IDNot Available
ChEBI ID7563
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [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. [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. [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. [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. [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. [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