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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-10-29 15:23:07 UTC
Update Date2021-09-14 15:47:52 UTC
HMDB IDHMDB0011178
Secondary Accession Numbers
  • HMDB11178
Metabolite Identification
Common NameProlylglycine
DescriptionProlylglycine is a dipeptide composed of proline and glycine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. It is found in urine (PMID: 3782411 ).
Structure
Data?1582752876
Synonyms
ValueSource
L-Pro-glyChEBI
L-ProlinylglycineChEBI
P-GChEBI
PGChEBI
Pro-glyChEBI
L-ProlylglycineHMDB
N-L-ProlylglycineHMDB
N-ProlylglycineHMDB
NSC 89175HMDB
p-g DipeptideHMDB
PG DipeptideHMDB
Proline glycine dipeptideHMDB
Proline-glycine dipeptideHMDB
Prolyl-glycineHMDB
ProlylglycineChEBI
Chemical FormulaC7H12N2O3
Average Molecular Weight172.1818
Monoisotopic Molecular Weight172.08479226
IUPAC Name2-{[(2S)-pyrrolidin-2-yl]formamido}acetic acid
Traditional NamePro-Gly
CAS Registry Number2578-57-6
SMILES
OC(=O)CNC(=O)[C@@H]1CCCN1
InChI Identifier
InChI=1S/C7H12N2O3/c10-6(11)4-9-7(12)5-2-1-3-8-5/h5,8H,1-4H2,(H,9,12)(H,10,11)/t5-/m0/s1
InChI KeyRNKSNIBMTUYWSH-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-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.91 g/LALOGPS
logP-2.9ALOGPS
logP-3.7ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.87 m³·mol⁻¹ChemAxon
Polarizability16.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+130.88330932474
DeepCCS[M-H]-128.44530932474
DeepCCS[M-2H]-164.08630932474
DeepCCS[M+Na]+139.33830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ProlylglycineOC(=O)CNC(=O)[C@@H]1CCCN12822.8Standard polar33892256
ProlylglycineOC(=O)CNC(=O)[C@@H]1CCCN11674.5Standard non polar33892256
ProlylglycineOC(=O)CNC(=O)[C@@H]1CCCN11837.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prolylglycine,1TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)[C@@H]1CCCN11797.3Semi standard non polar33892256
Prolylglycine,1TMS,isomer #2C[Si](C)(C)N(CC(=O)O)C(=O)[C@@H]1CCCN11774.7Semi standard non polar33892256
Prolylglycine,1TMS,isomer #3C[Si](C)(C)N1CCC[C@H]1C(=O)NCC(=O)O1826.0Semi standard non polar33892256
Prolylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1)[Si](C)(C)C1752.7Semi standard non polar33892256
Prolylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1)[Si](C)(C)C1785.9Standard non polar33892256
Prolylglycine,2TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1)[Si](C)(C)C2574.8Standard polar33892256
Prolylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CNC(=O)[C@@H]1CCCN1[Si](C)(C)C1795.5Semi standard non polar33892256
Prolylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CNC(=O)[C@@H]1CCCN1[Si](C)(C)C1817.0Standard non polar33892256
Prolylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CNC(=O)[C@@H]1CCCN1[Si](C)(C)C2468.9Standard polar33892256
Prolylglycine,2TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)[C@@H]1CCCN1[Si](C)(C)C1737.5Semi standard non polar33892256
Prolylglycine,2TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)[C@@H]1CCCN1[Si](C)(C)C1825.8Standard non polar33892256
Prolylglycine,2TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)[C@@H]1CCCN1[Si](C)(C)C2315.9Standard polar33892256
Prolylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1[Si](C)(C)C)[Si](C)(C)C1792.6Semi standard non polar33892256
Prolylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1[Si](C)(C)C)[Si](C)(C)C1889.2Standard non polar33892256
Prolylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1[Si](C)(C)C)[Si](C)(C)C2145.6Standard polar33892256
Prolylglycine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)[C@@H]1CCCN12045.6Semi standard non polar33892256
Prolylglycine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)[C@@H]1CCCN12018.2Semi standard non polar33892256
Prolylglycine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1CCC[C@H]1C(=O)NCC(=O)O2078.1Semi standard non polar33892256
Prolylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1)[Si](C)(C)C(C)(C)C2227.7Semi standard non polar33892256
Prolylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1)[Si](C)(C)C(C)(C)C2205.9Standard non polar33892256
Prolylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1)[Si](C)(C)C(C)(C)C2609.8Standard polar33892256
Prolylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C2292.2Semi standard non polar33892256
Prolylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C2225.0Standard non polar33892256
Prolylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C2575.8Standard polar33892256
Prolylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C2247.9Semi standard non polar33892256
Prolylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C2233.0Standard non polar33892256
Prolylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C2509.8Standard polar33892256
Prolylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2481.7Semi standard non polar33892256
Prolylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2476.8Standard non polar33892256
Prolylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2492.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Prolylglycine GC-MS (2 TMS)splash10-0006-2900000000-89799a6272194efe9d082014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prolylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 10V, Positive-QTOFsplash10-00di-6900000000-24972ffd24ebd14480862019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 20V, Positive-QTOFsplash10-00di-9000000000-f5860fa130816fb7c4632019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 40V, Positive-QTOFsplash10-00dl-9000000000-97f3a107affd584af8712019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 10V, Negative-QTOFsplash10-00di-0900000000-1add648393301d0feba12019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 20V, Negative-QTOFsplash10-00di-7900000000-b60a3bc21d3dd4103fff2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 40V, Negative-QTOFsplash10-00dl-9000000000-bc534a481231b926bd6c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 10V, Positive-QTOFsplash10-006t-9000000000-2e9e8efc641c3dfd18bb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 20V, Positive-QTOFsplash10-00di-9000000000-8f982a38658d827f57dc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 40V, Positive-QTOFsplash10-00di-9000000000-98be7b4ea7f8297650852021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 10V, Negative-QTOFsplash10-00di-1900000000-6445b0236efd5117342d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 20V, Negative-QTOFsplash10-00r2-9100000000-55c1fb3d336df678f0bd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolylglycine 40V, Negative-QTOFsplash10-014l-9000000000-834448a15433650416162021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.31 +/- 0.16 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00011257
Chemspider ID4932143
KEGG Compound IDNot Available
BioCyc IDCPD0-2182
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6426709
PDB IDNot Available
ChEBI ID61695
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. [PubMed:3782411 ]