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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:25 UTC
HMDB IDHMDB0000721
Secondary Accession Numbers
  • HMDB00721
Metabolite Identification
Common NameGlycylproline
DescriptionGlycylproline is a dipeptide composed of glycine and proline, and 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. Patients with this disease have reportedly decreased prolidase enzyme activity against glycylproline (Gly-Pro). The enzyme's activity against other substrates is not as affected. Some patients with prolidase deficiency have a marked urinary excretion of glycylproline. Patients with pressure sores contain significantly more urinary glycylproline than the control (PMID: 16009141 , 7629169 , 1536787 , 10582130 ).
Structure
Data?1563860665
Synonyms
ValueSource
1-(Aminoacetyl)prolineChEBI
1-GlycylprolineChEBI
Gly-L-proChEBI
GPChEBI
N-Glycyl-L-prolineChEBI
N-GlycylprolineChEBI
Glycyl-L-prolineHMDB
(S)-1-(2-Aminoacetyl)pyrrolidine-2-carboxylic acidHMDB
1-Glycyl-L-prolineHMDB
g-p DipeptideHMDB
GP DipeptideHMDB
Gly-proHMDB
Glycine proline dipeptideHMDB
Glycine-proline dipeptideHMDB
Glycyl-prolineHMDB
NSC 97929HMDB
GlycylprolineChEBI
Chemical FormulaC7H12N2O3
Average Molecular Weight172.1818
Monoisotopic Molecular Weight172.08479226
IUPAC Name(2S)-1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid
Traditional Nameglycylproline
CAS Registry Number704-15-4
SMILES
NCC(=O)N1CCC[C@H]1C(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)/t5-/m0/s1
InChI KeyKZNQNBZMBZJQJO-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Proline or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility279 g/LALOGPS
logP-2.6ALOGPS
logP-3.7ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)8.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.63 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.99 m³·mol⁻¹ChemAxon
Polarizability16.75 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2901000000-1b9ae10ce7fa6c3ddfbaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1901000000-f37ccc8ccf214e97d6b6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1901000000-f37ccc8ccf214e97d6b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1900000000-9da065ddc26b31b36592JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01b9-5900000000-583b4cb589c2ec738f36JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-7bdaea720328b0c3851eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1900000000-6987035260ca993cd43eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac0-9600000000-c74cee61fd2ec534af77JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-48d0c933c8b6f78e839fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0900000000-55b1206a1419a41e86ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-3900000000-6739642d8410a9a177edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-16170c56a5433313b0aaJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected and Quantified0 - 16.17 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 16.17 umol/mmol creatinineInfant (1 - 6 months old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 16.17 umol/mmol creatinineInfant (6 months - <1 year old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 16.17 umol/mmol creatinineChildren (1 - 2 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 16.17 umol/mmol creatinineChildren (2 - 4 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 16.17 umol/mmol creatinineChildren (4 - 13 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 16.17 umol/mmol creatinineAdolescent (13 - 21 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 16.17 umol/mmol creatinineAdult (>21 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified1.4-2.8 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified1.1-2.0 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified61.403 +/- 24.479 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.23 +/- 0.04 uMElderly (>65 years old)Both
Alzheimer's disease
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.086 +/- 0.016 uMElderly (>65 years old)BothAlzheimer's disease details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified590.8 +/- 81.14 umol/mmol creatinineAdult (>18 years old)Not SpecifiedProlidase deficiency details
UrineDetected and Quantified0.0087 +/- 0.0016 umol/mmol creatinineElderly (>65 years old)BothAlzheimer's disease details
UrineDetected and Quantified46.339 +/- 42.779 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Prolidase deficiency
  1. 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 ]
  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 ]
Alzheimer's disease
  1. 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 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022202
KNApSAcK IDNot Available
Chemspider ID2282246
KEGG Compound IDNot Available
BioCyc IDCPD-10814
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3013625
PDB IDNot Available
ChEBI ID70744
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceMaruyama, 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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]

Enzymes

General function:
Involved in cellular process
Specific function:
Splits dipeptides with a prolyl or hydroxyprolyl residue in the C-terminal position. Plays an important role in collagen metabolism because the high level of iminoacids in collagen
Gene Name:
PEPD
Uniprot ID:
P12955
Molecular weight:
54547.8
References
  1. Yuan J, Li T, Yin XB, Guo L, Jiang X, Jin W, Yang X, Wang E: Characterization of prolidase activity using capillary electrophoresis with tris(2,2'-bipyridyl)ruthenium(II) electrochemiluminescence detection and application to evaluate collagen degradation in diabetes mellitus. Anal Chem. 2006 May 1;78(9):2934-8. [PubMed:16642978 ]