Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:20:58 UTC

Update Date

2021-09-26 23:06:10 UTC

HMDB ID

HMDB0253141

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Description

Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione, also known as cyclo(gly-O-pro) or cyclo(glycylprolyl), 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. Based on a literature review very few articles have been published on Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cyclo(gly-O-pro)	MeSH
Cyclo(gly-pro)	MeSH
Cyclo(glycyl-L-prolyl)	MeSH
Cyclo(glycylprolyl)	MeSH
Cyclo(glycylprolyl), (L)-isomer	MeSH

Chemical Formula

C₇H₁₀N₂O₂

Average Molecular Weight

154.169

Monoisotopic Molecular Weight

154.07422757

IUPAC Name

octahydropyrrolo[1,2-a]piperazine-1,4-dione

Traditional Name

hexahydropyrrolo[1,2-a]piperazine-1,4-dione

CAS Registry Number

Not Available

SMILES

O=C1CNC(=O)C2CCCN12

InChI Identifier

InChI=1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)

InChI Key

OWOHLURDBZHNGG-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
N-alkylpiperazine
1,4-diazinane
Piperazine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.6	ALOGPS
logP	-1.4	ChemAxon
logS	0.11	ALOGPS
pKa (Strongest Acidic)	11.35	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37.79 m³·mol⁻¹	ChemAxon
Polarizability	15.12 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M-2H]-	166.916	30932474
DeepCCS	[M+Na]+	142.067	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	130.1	32859911
AllCCS	[M+Na-2H]-	131.1	32859911
AllCCS	[M+HCOO]-	132.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione	O=C1CNC(=O)C2CCCN12	2704.2	Standard polar	33892256
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione	O=C1CNC(=O)C2CCCN12	1247.7	Standard non polar	33892256
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione	O=C1CNC(=O)C2CCCN12	1769.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TMS,isomer #1	C[Si](C)(C)N1CC(=O)N2CCCC2C1=O	1695.7	Semi standard non polar	33892256
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TMS,isomer #1	C[Si](C)(C)N1CC(=O)N2CCCC2C1=O	1641.3	Standard non polar	33892256
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TMS,isomer #1	C[Si](C)(C)N1CC(=O)N2CCCC2C1=O	2403.4	Standard polar	33892256
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC(=O)N2CCCC2C1=O	1933.1	Semi standard non polar	33892256
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC(=O)N2CCCC2C1=O	1935.3	Standard non polar	33892256
Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC(=O)N2CCCC2C1=O	2614.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9400000000-71a4c134589c616209a9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 6V, Positive-QTOF	splash10-0a4i-1900000000-960260ac9b61daf622b6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Positive-QTOF	splash10-0a4i-0900000000-a88018c8bb2fc754b615	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 20V, Positive-QTOF	splash10-0ab9-7900000000-5536909a75162e2059c4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 40V, Positive-QTOF	splash10-00di-9000000000-a717ab0d5df61dc6844a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Negative-QTOF	splash10-0udi-0900000000-e02e71c66ee7cff07ec0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 20V, Negative-QTOF	splash10-0udi-4900000000-6e3033002877228e612a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 40V, Negative-QTOF	splash10-0006-9200000000-8cb046900d9e25311130	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

167952

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193540

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (HMDB0253141)

MOL for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D MOL for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D SDF for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D-SDF for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

PDB for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D PDB for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

SMILES for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

INCHI for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

Structure for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D Structure for HMDB0253141 (Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra