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Human Metabolome Database Version 3.5

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Showing metabocard for Glycylproline (HMDB00721)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:11 -0700
HMDB ID HMDB00721
Secondary Accession Numbers None
Metabolite Identification
Common Name Glycylproline
Description Glycylproline is an end product of collagen metabolism that is further cleaved by prolidase (EC 3.4.13.9); the resulting proline molecules are recycled into collagen or other proteins. Prolidase deficiency is a rare autosomal recessive disease characterized by chronic ulcerative dermatitis, mental retardation, frequent infections and massive urinary excretion of iminodipeptides. The disease has been confirmed to be due to hereditary prolidase deficiency. It has been reported that the activity of the enzyme against glycylproline (Gly-Pro) is almost totally deficient in patients with prolidase deficiency, whereas the activity against other substrates is not so deficient. Some patients with prolidase deficiency have a marked urinary excretion of the iminodipeptide Glycylproline. The urine from patients with pressure sores contains significantly more Glycylproline than the urine from the control. (PMID: 16009141 Link_out, 7629169 Link_out, 1536787 Link_out, 10582130 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-(Aminoacetyl)proline
  2. 1-Glycyl-L-Proline
  3. 1-Glycylproline
  4. GLY-pro
  5. N-Glycyl-L-proline
  6. N-Glycylproline
Chemical Formula C7H12N2O3
Average Molecular Weight 172.1818
Monoisotopic Molecular Weight 172.08479226
IUPAC Name 1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid
Traditional IUPAC Name 1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid
CAS Registry Number 704-15-4
SMILES NCC(=O)N1CCCC1C(O)=O
InChI Identifier InChI=1S/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)
InChI Key KZNQNBZMBZJQJO-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/A
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • a dipeptide(Cyc)
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrolidine
  • Pyrrolidine Carboxylic Acid
  • Tertiary Carboxylic Acid Amide
Direct Parent Peptides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 155 - 158 °C 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 279 g/L ALOGPS
LogP -2.65 ALOGPS
LogP -3.7 ChemAxon
LogS 0.21 ALOGPS
pKa (strongest acidic) 3.61 ChemAxon
pKa (strongest basic) 8.13 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 83.63 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 40.99 ChemAxon
Polarizability 16.6 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 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
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.4 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.23 +/- 0.04 uM Elderly (>65 years old) Both Alzheimer's disease Probable Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.086 +/- 0.016 uM Elderly (>65 years old) Both Alzheimer's disease Not Available
Urine Detected and Quantified
Article_icon
590.8 +/- 81.14 umol/mmol creatinine Adult (>18 years old) Not Specified Prolidase deficiency Not Available
Urine Detected and Quantified
Article_icon
0.0087 +/- 0.0016 umol/mmol creatinine Elderly (>65 years old) Both Alzheimer's disease Not Available
Associated Disorders and Diseases
Disease References
Prolidase deficiency
  • Barshop BA: Metabolomic approaches to mitochondrial disease: correlation of urine organic acids. Mitochondrion. 2004 Sep;4(5-6):521-7. Epub 2004 Sep 30. Pubmed: 16120410 Link_out
  • 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
    Alzheimer's disease
    • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022202
      KNApSAcK ID Not Available
      Chemspider ID 71432 Link_out
      KEGG Compound ID Not Available
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00721 Link_out
      Metagene Link HMDB00721 Link_out
      METLIN ID 5689 Link_out
      PubChem Compound 79101 Link_out
      PDB ID Not Available
      ChEBI ID 356660 Link_out
      References
      Synthesis Reference Maruyama, Susumu; Ichimura, Toshiaki; Otsuka, Tatsuo; Yamashita, Eiichi. Long-lasting antihypertensive agents and glycylproline manufactured from collagen and/or gelatin. Jpn. Kokai Tokkyo Koho (2005), 10 pp.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
      2. Barshop BA: Metabolomic approaches to mitochondrial disease: correlation of urine organic acids. Mitochondrion. 2004 Sep;4(5-6):521-7. Epub 2004 Sep 30. Pubmed: 16120410 Link_out
      3. Krepela E, Kasafirek E, Vicar J, Kraml J: An assay of dipeptidyl peptidase IV activity in human serum and serum of pregnant women with glycyl-L-proline-1-naphthylamide and other glycyl-L-proline-arylamides as substrates. Physiol Bohemoslov. 1983;32(4):334-45. Pubmed: 6353449 Link_out
      4. 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
      Enzymes
      Name: Xaa-Pro dipeptidase
      Reactions:
      • Hydrolysis of Xaa!Pro dipeptides
      • also acts on aminoacyl-hydroxyproline analogs. No action on Pro-Pro COFACTOR Manganese [CPD:C00034] EFFECTOR Thiol [CPD:C00145]
      Gene Name: PEPD
      Uniprot ID: P12955 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA