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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:23:21 UTC

Update Date

2021-09-26 22:57:02 UTC

HMDB ID

HMDB0247382

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate

Description

2,5-dioxopyrrolidin-1-yl 2-(acetylsulfanyl)acetate belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring. Based on a literature review very few articles have been published on 2,5-dioxopyrrolidin-1-yl 2-(acetylsulfanyl)acetate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,5-dioxopyrrolidin-1-yl 2-(acetylthio)acetate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 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


  Mrv1652309112102232D          

 15 15  0  0  0  0            999 V2000
    2.4489   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -3.3644    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -4.1894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213   -2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357   -3.3644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4894   -3.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6609   -2.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0414   -3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289   -4.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8220   -4.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2089   -4.7369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247382

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)SCC(=O)ON1C(=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H9NO5S/c1-5(10)15-4-8(13)14-9-6(11)2-3-7(9)12/h2-4H2,1H3

> <INCHI_KEY>
FLCQLSRLQIPNLM-UHFFFAOYSA-N

> <FORMULA>
C8H9NO5S

> <MOLECULAR_WEIGHT>
231.22

> <EXACT_MASS>
231.020143568

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.922239724390053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dioxopyrrolidin-1-yl 2-(acetylsulfanyl)acetate

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
-0.7865873473333331

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.70656722495593

> <JCHEM_PKA_STRONGEST_BASIC>
-6.032083087118271

> <JCHEM_POLAR_SURFACE_AREA>
80.75

> <JCHEM_REFRACTIVITY>
50.4945

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dioxopyrrolidin-1-yl (acetylsulfanyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       4.571  -6.280   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.905  -5.510   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.905  -3.970   0.000  0.00  0.00           O+0
HETATM    4  S   UNK     0       7.239  -6.280   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       8.572  -5.510   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.906  -6.280   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.906  -7.820   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.240  -5.510   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      12.573  -6.280   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      13.980  -5.654   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.300  -4.147   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      15.011  -6.798   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.241  -8.132   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.734  -7.812   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.590  -8.842   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,5-Dioxopyrrolidin-1-yl 2-(acetylsulfanyl)acetic acid	Generator
2,5-Dioxopyrrolidin-1-yl 2-(acetylsulphanyl)acetate	Generator
2,5-Dioxopyrrolidin-1-yl 2-(acetylsulphanyl)acetic acid	Generator
2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetic acid	Generator
HSATA	MeSH
N-Hydroxysuccinimide S-acetylthioacetate	MeSH
N-Succinimidyl-S-acetylthioacetate	MeSH
S-Acetylthioacetic acid N-hydroxysuccinimide ester	MeSH
SATA	MeSH

Chemical Formula

C₈H₉NO₅S

Average Molecular Weight

231.22

Monoisotopic Molecular Weight

231.020143568

IUPAC Name

2,5-dioxopyrrolidin-1-yl 2-(acetylsulfanyl)acetate

Traditional Name

2,5-dioxopyrrolidin-1-yl (acetylsulfanyl)acetate

CAS Registry Number

Not Available

SMILES

CC(=O)SCC(=O)ON1C(=O)CCC1=O

InChI Identifier

InChI=1S/C8H9NO5S/c1-5(10)15-4-8(13)14-9-6(11)2-3-7(9)12/h2-4H2,1H3

InChI Key

FLCQLSRLQIPNLM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Pyrrolidones

Direct Parent

Pyrrolidine-2-ones

Alternative Parents

Substituents

2-pyrrolidone
Dicarboximide
Carboxylic acid salt
Lactam
Thiocarboxylic acid ester
Carbothioic s-ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Thiocarboxylic acid or derivatives
Sulfenyl compound
Azacycle
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic salt
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	0.09	ALOGPS
logP	-0.79	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	17.71	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	80.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	50.49 m³·mol⁻¹	ChemAxon
Polarizability	20.92 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
DeepCCS	[M+H]+	137.614	30932474
DeepCCS	[M-H]-	134.852	30932474
DeepCCS	[M-2H]-	170.967	30932474
DeepCCS	[M+Na]+	146.506	30932474
AllCCS	[M+H]+	146.8	32859911
AllCCS	[M+H-H2O]+	143.2	32859911
AllCCS	[M+NH4]+	150.2	32859911
AllCCS	[M+Na]+	151.1	32859911
AllCCS	[M-H]-	147.1	32859911
AllCCS	[M+Na-2H]-	147.6	32859911
AllCCS	[M+HCOO]-	148.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate	CC(=O)SCC(=O)ON1C(=O)CCC1=O	3035.6	Standard polar	33892256
2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate	CC(=O)SCC(=O)ON1C(=O)CCC1=O	1869.1	Standard non polar	33892256
2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate	CC(=O)SCC(=O)ON1C(=O)CCC1=O	2004.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ou-9400000000-25b3268330f189783aea	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 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 - 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 10V, Positive-QTOF	splash10-001i-1190000000-d9f6600993d59e685caa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 20V, Positive-QTOF	splash10-0006-9100000000-9f79517d9e4090911bc7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 40V, Positive-QTOF	splash10-0006-9300000000-d2fd74bb30a3f9262f5a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 10V, Negative-QTOF	splash10-000x-9320000000-3b59d02944662236ebca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 20V, Negative-QTOF	splash10-00dm-9000000000-f270bfd6a94ec975eeb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate 40V, Negative-QTOF	splash10-00di-9000000000-92f317aca0e25c2b2c43	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

113145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate (HMDB0247382)

MOL for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

3D MOL for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

3D SDF for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

3D-SDF for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

PDB for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

3D PDB for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

SMILES for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

INCHI for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

Structure for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

3D Structure for HMDB0247382 (2,5-Dioxopyrrolidin-1-yl 2-(acetylthio)acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra