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Human Metabolome Database Version 3.5

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Showing metabocard for Hexanoylglycine (HMDB00701)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:08 -0700
HMDB ID HMDB00701
Secondary Accession Numbers None
Metabolite Identification
Common Name Hexanoylglycine
Description Hexanoylglycine 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-acylglycineHexanoylglycine is a fatty acid metabolite, it appears in the urine of patients with hereditary medium-chain acyl-CoA dehydrogenase (MCAD) deficiency (PMID 2775902 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Caproylglycine
  2. Hexanoylglycine
  3. N-Caproylglycine
  4. N-Hexanoyl-Glycine
  5. N-Hexanoylglycine
Chemical Formula C8H15NO3
Average Molecular Weight 173.2096
Monoisotopic Molecular Weight 173.105193351
IUPAC Name 2-hexanamidoacetic acid
Traditional IUPAC Name hexanamidoacetic acid
CAS Registry Number 24003-67-6
SMILES CCCCCC(=O)NCC(O)=O
InChI Identifier InChI=1S/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)
InChI Key UPCKIPHSXMXJOX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Alpha Amino Acids and Derivatives
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • N Acyl Amine
  • Secondary Carboxylic Acid Amide
Direct Parent Acyl Glycines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.61 g/L ALOGPS
LogP 0.90 ALOGPS
LogP 0.71 ChemAxon
LogS -1.68 ALOGPS
pKa (strongest acidic) 4.25 ChemAxon
pKa (strongest basic) -0.95 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.4 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 43.88 ChemAxon
Polarizability 18.74 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.41 +/- 1.72 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
1.00 (0.0-2.0) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
366.0 (2.00-730.00) umol/mmol creatinine Adult (>18 years old) Both Medium chain acyl CoA dehydrogenase deficiency Not Available
Urine Detected and Quantified
Article_icon
1.6 (0.00-3.26) umol/mmol creatinine Adult (>18 years old) Both Short chain acyl -CoA dehydrogenase deficiency (SCAD) Not Available
Associated Disorders and Diseases
Disease References
Medium Chain Acyl-CoA Dehydrogenase Deficiency
    • http://www.metagene.de/program/d.prg?mp=MEDIUM%20CHAIN%20ACYL-COA%20DEHYDROGENASE%20DEFICIENCY%20(MCAD)
    Short Chain Acyl-Coa Dehydrogenase Deficiency
      • http://www.metagene.de/program/d.prg?mp=SHORT%20CHAIN%20ACYL-COA%20DEHYDROGENASE%20DEFICIENCY%20(SCAD)
      Associated OMIM IDs
      • 201450 Link_out (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022190
      KNApSAcK ID Not Available
      Chemspider ID 89859 Link_out
      KEGG Compound ID Not Available
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00701 Link_out
      Metagene Link HMDB00701 Link_out
      METLIN ID 5669 Link_out
      PubChem Compound 99463 Link_out
      PDB ID Not Available
      ChEBI ID 64390 Link_out
      References
      Synthesis Reference Toth, Eugene; Weiss, Benjamine; Banay-Schwartz, Miriam; Lajtha, Abel. Effect of glycine derivatives on behavioral changes induced by 3-mercaptopropionic acid or phencyclidine in mice. Research Communications in Psychology, Psychiatry and Behavior (1986), 11(1), 1-9.
      Material Safety Data Sheet (MSDS) Not Available
      General References
      1. Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: Stable isotope dilution analysis of n-hexanoylglycine, 3-phenylpropionylglycine and suberylglycine in human urine using chemical ionization gas chromatography/mass spectrometry selected ion monitoring. Biomed Environ Mass Spectrom. 1989 Jul;18(7):471-7. Pubmed: 2775902 Link_out
      2. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685 Link_out
      3. Chabrol B, Mancini J, Bertrand C, Vianey-Saban C, Divry P, Livet MO, Pinsard N: [Generalized epilepsy disclosing medium-chain-acyl-CoA dehydrogenase deficiency] Arch Fr Pediatr. 1993 Jun-Jul;50(6):497-500. Pubmed: 8135611 Link_out
      4. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. Pubmed: 2380628 Link_out
      5. Yamaguchi S, Shimizu N, Orii T, Fukao T, Suzuki Y, Maeda K, Hashimoto T, Previs SF, Rinaldo P: Prenatal diagnosis and neonatal monitoring of a fetus with glutaric aciduria type II due to electron transfer flavoprotein (beta-subunit) deficiency. Pediatr Res. 1991 Nov;30(5):439-43. Pubmed: 1754299 Link_out
      Enzymes
      Name: Glycine N-acyltransferase
      Reactions:
      • acyl-CoA + glycine = CoA + N-acylglycine [RN:R00395]
      Gene Name: GLYAT
      Uniprot ID: Q6IB77 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glycine N-acyltransferase-like protein 1
      Reactions:
      • acyl-CoA + glycine = CoA + N-acylglycine [RN:R00395]
      Gene Name: GLYATL1
      Uniprot ID: Q969I3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glycine N-acyltransferase-like protein 2
      Reactions:
      • acyl-CoA + glycine = CoA + N-acylglycine [RN:R00395]
      Gene Name: GLYATL2
      Uniprot ID: Q8WU03 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glycine N-acyltransferase-like protein 3
      Reactions:
        Gene Name: GLYATL3
        Uniprot ID: Q5SZD4 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA