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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:59 UTC
Update Date2022-03-07 02:53:01 UTC
HMDB IDHMDB0031547
Secondary Accession Numbers
  • HMDB31547
Metabolite Identification
Common NameL-Cyclo(alanylglycyl)
DescriptionL-Cyclo(alanylglycyl), also known as alanylglycine anhydride or cyclo(ala-gly), belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L-Cyclo(alanylglycyl) is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on L-Cyclo(alanylglycyl).
Structure
Data?1563862139
Synonyms
ValueSource
3-Methyl-2,5-dioxopiperazineChEBI
3-Methyl-2,5-piperazinedioneChEBI
Alanylglycine anhydrideChEBI
Cyclo(ala-gly)ChEBI
Cyclo(alanyl-glycyl)ChEBI
Cyclo(alanylglycyl)ChEBI
CycloglycylalanineChEBI
Glycylalanine anhydrideChEBI
3-Methyl-(S)-2,5-piperazinedioneHMDB
3-Methylpiperazine-2,5-dioneHMDB
L-3-Methyl-2,5-piperazinedioneHMDB
L-Alanylglycine anhydrideHMDB
L-Cyclo(alanyl-glycyl)HMDB
L-Glycylalanine anhydrideHMDB
L-MethyldiacipiperazineHMDB
Chemical FormulaC5H8N2O2
Average Molecular Weight128.1292
Monoisotopic Molecular Weight128.05857751
IUPAC Name3-methylpiperazine-2,5-dione
Traditional Name3-methylpiperazine-2,5-dione
CAS Registry Number4526-77-6
SMILES
CC1NC(=O)CNC1=O
InChI Identifier
InChI=1S/C5H8N2O2/c1-3-5(9)6-2-4(8)7-3/h3H,2H2,1H3,(H,6,9)(H,7,8)
InChI KeyICCHEGCKVBMSTF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • 1,4-diazinane
  • Piperazine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point247 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility250 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility22.1 g/LALOGPS
logP-1.6ALOGPS
logP-1.6ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)10.94ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.1 m³·mol⁻¹ChemAxon
Polarizability12.03 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
DarkChem[M+H]+128.36231661259
DarkChem[M-H]-120.17531661259
DeepCCS[M+H]+126.65530932474
DeepCCS[M-H]-123.75330932474
DeepCCS[M-2H]-160.13330932474
DeepCCS[M+Na]+135.16930932474
AllCCS[M+H]+127.432859911
AllCCS[M+H-H2O]+122.732859911
AllCCS[M+NH4]+131.832859911
AllCCS[M+Na]+133.132859911
AllCCS[M-H]-122.932859911
AllCCS[M+Na-2H]-125.032859911
AllCCS[M+HCOO]-127.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-Cyclo(alanylglycyl)CC1NC(=O)CNC1=O2497.6Standard polar33892256
L-Cyclo(alanylglycyl)CC1NC(=O)CNC1=O1117.6Standard non polar33892256
L-Cyclo(alanylglycyl)CC1NC(=O)CNC1=O1536.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Cyclo(alanylglycyl),1TMS,isomer #1CC1C(=O)NCC(=O)N1[Si](C)(C)C1423.3Semi standard non polar33892256
L-Cyclo(alanylglycyl),1TMS,isomer #1CC1C(=O)NCC(=O)N1[Si](C)(C)C1432.7Standard non polar33892256
L-Cyclo(alanylglycyl),1TMS,isomer #2CC1NC(=O)CN([Si](C)(C)C)C1=O1422.7Semi standard non polar33892256
L-Cyclo(alanylglycyl),1TMS,isomer #2CC1NC(=O)CN([Si](C)(C)C)C1=O1435.3Standard non polar33892256
L-Cyclo(alanylglycyl),2TMS,isomer #1CC1C(=O)N([Si](C)(C)C)CC(=O)N1[Si](C)(C)C1411.8Semi standard non polar33892256
L-Cyclo(alanylglycyl),2TMS,isomer #1CC1C(=O)N([Si](C)(C)C)CC(=O)N1[Si](C)(C)C1574.1Standard non polar33892256
L-Cyclo(alanylglycyl),1TBDMS,isomer #1CC1C(=O)NCC(=O)N1[Si](C)(C)C(C)(C)C1697.7Semi standard non polar33892256
L-Cyclo(alanylglycyl),1TBDMS,isomer #1CC1C(=O)NCC(=O)N1[Si](C)(C)C(C)(C)C1704.3Standard non polar33892256
L-Cyclo(alanylglycyl),1TBDMS,isomer #2CC1NC(=O)CN([Si](C)(C)C(C)(C)C)C1=O1699.9Semi standard non polar33892256
L-Cyclo(alanylglycyl),1TBDMS,isomer #2CC1NC(=O)CN([Si](C)(C)C(C)(C)C)C1=O1717.8Standard non polar33892256
L-Cyclo(alanylglycyl),2TBDMS,isomer #1CC1C(=O)N([Si](C)(C)C(C)(C)C)CC(=O)N1[Si](C)(C)C(C)(C)C1919.5Semi standard non polar33892256
L-Cyclo(alanylglycyl),2TBDMS,isomer #1CC1C(=O)N([Si](C)(C)C(C)(C)C)CC(=O)N1[Si](C)(C)C(C)(C)C2060.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-Cyclo(alanylglycyl) EI-B (Non-derivatized)splash10-053l-9000000000-a112f748d81443ef43d62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Cyclo(alanylglycyl) EI-B (Non-derivatized)splash10-000i-9100000000-235aec5f8d254471ac732017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Cyclo(alanylglycyl) EI-B (Non-derivatized)splash10-053l-9000000000-a112f748d81443ef43d62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Cyclo(alanylglycyl) EI-B (Non-derivatized)splash10-000i-9100000000-235aec5f8d254471ac732018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Cyclo(alanylglycyl) GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9200000000-81f0137991f4a9549c942017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Cyclo(alanylglycyl) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Cyclo(alanylglycyl) 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 - L-Cyclo(alanylglycyl) 10V, Positive-QTOFsplash10-004i-1900000000-ef58841914083a2020e92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 20V, Positive-QTOFsplash10-004i-5900000000-1248babcc12c1daf04b72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 40V, Positive-QTOFsplash10-0a4l-9000000000-6990706ff3f54b112e912015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 10V, Negative-QTOFsplash10-004i-3900000000-eb864f62f89c6f8050382015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 20V, Negative-QTOFsplash10-0006-9000000000-b9575017ddb5f3da293f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 40V, Negative-QTOFsplash10-0006-9000000000-8b70a383bfb6a721df1b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 10V, Positive-QTOFsplash10-004i-0900000000-ea63dbea5fcc8c72bee52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 20V, Positive-QTOFsplash10-002f-9400000000-347052fca3e9ef72e11d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 40V, Positive-QTOFsplash10-0006-9000000000-f4459dd06f2db29266672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 10V, Negative-QTOFsplash10-004i-4900000000-9c2129a2c0d7371bad6e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 20V, Negative-QTOFsplash10-002f-9200000000-f7f8d36b548acc43c4f62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 40V, Negative-QTOFsplash10-0006-9000000000-33f1e7be75dadd1e6d562021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008158
KNApSAcK IDNot Available
Chemspider ID96562
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107297
PDB IDNot Available
ChEBI ID144050
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .