Human Metabolome Database Version 3.5

Showing metabocard for Glycylproline (HMDB00721)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:28:45 -0600
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 | PDB | 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 Reference
Urine Detected and Quantified
0.4 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.23 +/- 0.04 uM Elderly (>65 years old) Both Comment Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.086 +/- 0.016 uM Elderly (>65 years old) Both Alzheimer's disease
Urine Detected and Quantified 590.8 +/- 81.14 umol/mmol creatinine Adult (>18 years old) Not Specified Prolidase deficiency
Urine Detected and Quantified 0.0087 +/- 0.0016 umol/mmol creatinine Elderly (>65 years old) Both Alzheimer's disease
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
          DrugBank Metabolite 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
          5. Liu G, Nakayama K, Sagara Y, Awata S, Yamashita K, Manabe M, Kodama H: Characterization of prolidase activity in erythrocytes from a patient with prolidase deficiency: comparison with prolidase I and II purified from normal human erythrocytes. Clin Biochem. 2005 Jul;38(7):625-31. Pubmed: 16009141 Link_out
          6. Mock WL, Liu Y: Hydrolysis of picolinylprolines by prolidase. A general mechanism for the dual-metal ion containing aminopeptidases. J Biol Chem. 1995 Aug 4;270(31):18437-46. Pubmed: 7629169 Link_out
          7. Berardesca E, Fideli D, Bellosta M, Dyne KM, Zanaboni G, Cetta G: Blood transfusions in the therapy of a case of prolidase deficiency. Br J Dermatol. 1992 Feb;126(2):193-5. Pubmed: 1536787 Link_out
          8. Le J, Perier C, Peyroche S, Rascle F, Blanchon MA, Gonthier R, Frey J, Chamson A: Urine glycyl-L-proline increase and skin trophicity. Amino Acids. 1999;17(3):315-22. Pubmed: 10582130 Link_out

          Enzymes
          Name: Xaa-Pro dipeptidase
          Reactions: Not Available
          Gene Name: PEPD
          Uniprot ID: P12955 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA