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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-27 01:12:24 UTC

Update Date

2022-09-22 18:34:34 UTC

HMDB ID

HMDB0242137

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Description

(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione, also known as cyclo(prolylglycyl), 17O- and 15N-labeled or cyclo(pro-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. Based on a literature review very few articles have been published on (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cyclo(prolylglycyl), 17O- and 15N-labeled	HMDB
Cyclo(pro-O-gly)	HMDB
Cyclo(pro-gly)	HMDB
Cyclo(prolyl-glycyl)	HMDB
Cyclo-(pro-gly)	HMDB
Cyclo-prolylglycine	HMDB
Cycloprolylglycine	HMDB
Cyclo(gly-O-pro)	HMDB
Cyclo(gly-pro)	HMDB
Cyclo(glycylprolyl)	HMDB
Cyclo(prolylglycyl)	HMDB
Cyclo(glycylprolyl), (L)-isomer	HMDB
Cyclo(glycyl-L-prolyl)	HMDB

Chemical Formula

C₇H₁₀N₂O₂

Average Molecular Weight

154.1665

Monoisotopic Molecular Weight

154.074227574

IUPAC Name

(8aS)-octahydropyrrolo[1,2-a]piperazine-1,4-dione

Traditional Name

(8aS)-hexahydropyrrolo[1,2-a]piperazine-1,4-dione

CAS Registry Number

Not Available

SMILES

O=C1CNC(=O)[C@@H]2CCCN12

InChI Identifier

InChI=1S/C7H10N2O2/c10-6-4-8-7(11)5-2-1-3-9(5)6/h5H,1-4H2,(H,8,11)/t5-/m0/s1

InChI Key

OWOHLURDBZHNGG-YFKPBYRVSA-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

Not Available

Not Available

Not Available

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]-	166.772	30932474
DeepCCS	[M+Na]+	142.183	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.2	32859911
AllCCS	[M-H]-	129.3	32859911
AllCCS	[M+Na-2H]-	130.2	32859911
AllCCS	[M+HCOO]-	131.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione	O=C1CNC(=O)[C@@H]2CCCN12	2650.0	Standard polar	33892256
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione	O=C1CNC(=O)[C@@H]2CCCN12	1308.3	Standard non polar	33892256
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione	O=C1CNC(=O)[C@@H]2CCCN12	1771.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TMS,isomer #1	C[Si](C)(C)N1CC(=O)N2CCC[C@H]2C1=O	1690.2	Semi standard non polar	33892256
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TMS,isomer #1	C[Si](C)(C)N1CC(=O)N2CCC[C@H]2C1=O	1646.7	Standard non polar	33892256
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TMS,isomer #1	C[Si](C)(C)N1CC(=O)N2CCC[C@H]2C1=O	2453.5	Standard polar	33892256
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC(=O)N2CCC[C@H]2C1=O	1950.7	Semi standard non polar	33892256
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC(=O)N2CCC[C@H]2C1=O	1935.6	Standard non polar	33892256
(S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CC(=O)N2CCC[C@H]2C1=O	2657.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-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 - (S)-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 - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Positive-QTOF	splash10-0a4i-0900000000-4bcafb51a4771ba53a35	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Positive-QTOF	splash10-0a4i-1900000000-01d9fcd2909c5db0f24a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Positive-QTOF	splash10-0a4i-1900000000-960260ac9b61daf622b6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Positive-QTOF	splash10-0a4i-0900000000-76f927e7cc599035c0aa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 50V, Positive-QTOF	splash10-0002-0900000000-ebbbc504a0c8b516ebd5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 30V, Positive-QTOF	splash10-0002-9400000000-b583ceeb14e83bb85c5d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 30V, Positive-QTOF	splash10-0a4i-3900000000-f842a34087a3fb2059c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 50V, Positive-QTOF	splash10-004i-9000000000-3ec5bb9c9db69d35abca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 30V, Positive-QTOF	splash10-00di-9000000000-17e4f6ea56ba777dbbf3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Positive-QTOF	splash10-0a4i-0900000000-2c49ff14e47cb122fa8f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Positive-QTOF	splash10-0a4i-0900000000-0eabc91a5fdf51914e73	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Positive-QTOF	splash10-0a4i-0900000000-ff0f354d0495dbb48624	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 20V, Positive-QTOF	splash10-0a4i-1900000000-4a5302029faef6bdb2c6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 40V, Positive-QTOF	splash10-006x-9000000000-865e8b098bc7111f5db8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 10V, Negative-QTOF	splash10-0udi-2900000000-437c010e2c5b80bb4a42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 20V, Negative-QTOF	splash10-0udl-9500000000-05338d84da56af99f759	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 40V, Negative-QTOF	splash10-0gbc-9000000000-969b67a26d712b6e8ef2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-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 - (S)-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 - (S)-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 - (S)-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 - (S)-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 - (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 40V, Negative-QTOF	splash10-0006-9200000000-8cb046900d9e25311130	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04541

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

112149

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126154

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

Kong SW, Hernandez-Ferrer C: Assessment of coverage for endogenous metabolites and exogenous chemical compounds using an untargeted metabolomics platform. Pac Symp Biocomput. 2020;25:587-598. [PubMed:31797630 ]

Showing metabocard for (S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (HMDB0242137)

MOL for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D MOL for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D SDF for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D-SDF for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

PDB for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D PDB for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

SMILES for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

INCHI for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

Structure for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D Structure for HMDB0242137 ((S)-Hexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra