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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:59 UTC

Update Date

2023-02-21 17:20:47 UTC

HMDB ID

HMDB0031547

Secondary Accession Numbers

HMDB31547

Metabolite Identification

Common Name

L-Cyclo(alanylglycyl)

Description

L-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methyl-2,5-dioxopiperazine	ChEBI
3-Methyl-2,5-piperazinedione	ChEBI
Alanylglycine anhydride	ChEBI
Cyclo(ala-gly)	ChEBI
Cyclo(alanyl-glycyl)	ChEBI
Cyclo(alanylglycyl)	ChEBI
Cycloglycylalanine	ChEBI
Glycylalanine anhydride	ChEBI
3-Methyl-(S)-2,5-piperazinedione	HMDB
3-Methylpiperazine-2,5-dione	HMDB
L-3-Methyl-2,5-piperazinedione	HMDB
L-Alanylglycine anhydride	HMDB
L-Cyclo(alanyl-glycyl)	HMDB
L-Glycylalanine anhydride	HMDB
L-Methyldiacipiperazine	HMDB

Chemical Formula

C₅H₈N₂O₂

Average Molecular Weight

128.1292

Monoisotopic Molecular Weight

128.05857751

IUPAC Name

3-methylpiperazine-2,5-dione

Traditional Name

3-methylpiperazine-2,5-dione

CAS Registry Number

4526-77-6

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 Key

ICCHEGCKVBMSTF-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031547)
Cytoplasm (HMDB: HMDB0031547)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031547)

Source

Endogenous

Endogenous (HMDB: HMDB0031547)

Plant

Theobroma cacao (HMDB: HMDB0031547)

Exogenous

Food

Food (HMDB: HMDB0031547)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Exogenous (HMDB: HMDB0031547)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	247 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	250 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	22.1 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.6	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	10.94	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.1 m³·mol⁻¹	ChemAxon
Polarizability	12.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.362	31661259
DarkChem	[M-H]-	120.175	31661259
DeepCCS	[M+H]+	126.655	30932474
DeepCCS	[M-H]-	123.753	30932474
DeepCCS	[M-2H]-	160.133	30932474
DeepCCS	[M+Na]+	135.169	30932474
AllCCS	[M+H]+	127.4	32859911
AllCCS	[M+H-H2O]+	122.7	32859911
AllCCS	[M+NH4]+	131.8	32859911
AllCCS	[M+Na]+	133.1	32859911
AllCCS	[M-H]-	122.9	32859911
AllCCS	[M+Na-2H]-	125.0	32859911
AllCCS	[M+HCOO]-	127.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Cyclo(alanylglycyl)	CC1NC(=O)CNC1=O	2497.6	Standard polar	33892256
L-Cyclo(alanylglycyl)	CC1NC(=O)CNC1=O	1117.6	Standard non polar	33892256
L-Cyclo(alanylglycyl)	CC1NC(=O)CNC1=O	1536.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Cyclo(alanylglycyl),1TMS,isomer #1	CC1C(=O)NCC(=O)N1[Si](C)(C)C	1423.3	Semi standard non polar	33892256
L-Cyclo(alanylglycyl),1TMS,isomer #1	CC1C(=O)NCC(=O)N1[Si](C)(C)C	1432.7	Standard non polar	33892256
L-Cyclo(alanylglycyl),1TMS,isomer #2	CC1NC(=O)CN([Si](C)(C)C)C1=O	1422.7	Semi standard non polar	33892256
L-Cyclo(alanylglycyl),1TMS,isomer #2	CC1NC(=O)CN([Si](C)(C)C)C1=O	1435.3	Standard non polar	33892256
L-Cyclo(alanylglycyl),2TMS,isomer #1	CC1C(=O)N([Si](C)(C)C)CC(=O)N1[Si](C)(C)C	1411.8	Semi standard non polar	33892256
L-Cyclo(alanylglycyl),2TMS,isomer #1	CC1C(=O)N([Si](C)(C)C)CC(=O)N1[Si](C)(C)C	1574.1	Standard non polar	33892256
L-Cyclo(alanylglycyl),1TBDMS,isomer #1	CC1C(=O)NCC(=O)N1[Si](C)(C)C(C)(C)C	1697.7	Semi standard non polar	33892256
L-Cyclo(alanylglycyl),1TBDMS,isomer #1	CC1C(=O)NCC(=O)N1[Si](C)(C)C(C)(C)C	1704.3	Standard non polar	33892256
L-Cyclo(alanylglycyl),1TBDMS,isomer #2	CC1NC(=O)CN([Si](C)(C)C(C)(C)C)C1=O	1699.9	Semi standard non polar	33892256
L-Cyclo(alanylglycyl),1TBDMS,isomer #2	CC1NC(=O)CN([Si](C)(C)C(C)(C)C)C1=O	1717.8	Standard non polar	33892256
L-Cyclo(alanylglycyl),2TBDMS,isomer #1	CC1C(=O)N([Si](C)(C)C(C)(C)C)CC(=O)N1[Si](C)(C)C(C)(C)C	1919.5	Semi standard non polar	33892256
L-Cyclo(alanylglycyl),2TBDMS,isomer #1	CC1C(=O)N([Si](C)(C)C(C)(C)C)CC(=O)N1[Si](C)(C)C(C)(C)C	2060.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - L-Cyclo(alanylglycyl) EI-B (Non-derivatized)	splash10-053l-9000000000-a112f748d81443ef43d6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Cyclo(alanylglycyl) EI-B (Non-derivatized)	splash10-000i-9100000000-235aec5f8d254471ac73	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Cyclo(alanylglycyl) EI-B (Non-derivatized)	splash10-053l-9000000000-a112f748d81443ef43d6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Cyclo(alanylglycyl) EI-B (Non-derivatized)	splash10-000i-9100000000-235aec5f8d254471ac73	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Cyclo(alanylglycyl) GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9200000000-81f0137991f4a9549c94	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Cyclo(alanylglycyl) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Cyclo(alanylglycyl) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 10V, Positive-QTOF	splash10-004i-1900000000-ef58841914083a2020e9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 20V, Positive-QTOF	splash10-004i-5900000000-1248babcc12c1daf04b7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 40V, Positive-QTOF	splash10-0a4l-9000000000-6990706ff3f54b112e91	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 10V, Negative-QTOF	splash10-004i-3900000000-eb864f62f89c6f805038	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 20V, Negative-QTOF	splash10-0006-9000000000-b9575017ddb5f3da293f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 40V, Negative-QTOF	splash10-0006-9000000000-8b70a383bfb6a721df1b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 10V, Positive-QTOF	splash10-004i-0900000000-ea63dbea5fcc8c72bee5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 20V, Positive-QTOF	splash10-002f-9400000000-347052fca3e9ef72e11d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 40V, Positive-QTOF	splash10-0006-9000000000-f4459dd06f2db2926667	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 10V, Negative-QTOF	splash10-004i-4900000000-9c2129a2c0d7371bad6e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 20V, Negative-QTOF	splash10-002f-9200000000-f7f8d36b548acc43c4f6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Cyclo(alanylglycyl) 40V, Negative-QTOF	splash10-0006-9000000000-33f1e7be75dadd1e6d56	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008158

KNApSAcK ID

Not Available

Chemspider ID

96562

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107297

PDB ID

Not Available

ChEBI ID

144050

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for L-Cyclo(alanylglycyl) (HMDB0031547)

MOL for HMDB0031547 (L-Cyclo(alanylglycyl))

3D MOL for HMDB0031547 (L-Cyclo(alanylglycyl))

3D SDF for HMDB0031547 (L-Cyclo(alanylglycyl))

3D-SDF for HMDB0031547 (L-Cyclo(alanylglycyl))

PDB for HMDB0031547 (L-Cyclo(alanylglycyl))

3D PDB for HMDB0031547 (L-Cyclo(alanylglycyl))

SMILES for HMDB0031547 (L-Cyclo(alanylglycyl))

INCHI for HMDB0031547 (L-Cyclo(alanylglycyl))

Structure for HMDB0031547 (L-Cyclo(alanylglycyl))

3D Structure for HMDB0031547 (L-Cyclo(alanylglycyl))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra