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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:18:58 UTC

Update Date

2021-09-26 23:13:41 UTC

HMDB ID

HMDB0257379

Secondary Accession Numbers

None

Metabolite Identification

Common Name

S-(1,2-dichlorovinyl)-L-cysteine sulfoxide

Description

2-amino-3-(1,2-dichloroethenesulfinyl)propanoic acid belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Based on a literature review very few articles have been published on 2-amino-3-(1,2-dichloroethenesulfinyl)propanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). S-(1,2-dichlorovinyl)-l-cysteine sulfoxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically S-(1,2-dichlorovinyl)-L-cysteine sulfoxide 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

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       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       2.310  -0.206   0.000  0.00  0.00           N+0
HETATM    7  S   UNK     0       4.977   1.334   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       8.978   2.104   0.000  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0       6.311   3.644   0.000  0.00  0.00          Cl+0
CONECT    1    2    7                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Amino-3-(1,2-dichloroethenesulfinyl)propanoate	Generator
2-Amino-3-(1,2-dichloroethenesulphinyl)propanoate	Generator
2-Amino-3-(1,2-dichloroethenesulphinyl)propanoic acid	Generator
S-(1,2-Dichlorovinyl)-L-cysteine sulphoxide	Generator

Chemical Formula

C₅H₇Cl₂NO₃S

Average Molecular Weight

232.08

Monoisotopic Molecular Weight

230.9523697

IUPAC Name

2-amino-3-(1,2-dichloroethenesulfinyl)propanoic acid

Traditional Name

2-amino-3-(1,2-dichloroethenesulfinyl)propanoic acid

CAS Registry Number

Not Available

SMILES

NC(CS(=O)C(Cl)=CCl)C(O)=O

InChI Identifier

InChI=1S/C5H7Cl2NO3S/c6-1-4(7)12(11)2-3(8)5(9)10/h1,3H,2,8H2,(H,9,10)

InChI Key

MSOVYRJYSIWWPY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

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

Alternative Parents

Substituents

Alpha-amino acid
Sulfoxide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Vinyl chloride
Vinyl halide
Sulfinyl compound
Haloalkene
Chloroalkene
Amine
Organic oxygen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

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	-1.2	ALOGPS
logP	-2.2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.26	ChemAxon
pKa (Strongest Basic)	8.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	46.49 m³·mol⁻¹	ChemAxon
Polarizability	19.68 Å³	ChemAxon
Number of Rings	0	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]+	139.347	30932474
DeepCCS	[M-H]-	135.518	30932474
DeepCCS	[M-2H]-	172.711	30932474
DeepCCS	[M+Na]+	148.287	30932474
AllCCS	[M+H]+	145.6	32859911
AllCCS	[M+H-H2O]+	142.2	32859911
AllCCS	[M+NH4]+	148.7	32859911
AllCCS	[M+Na]+	149.6	32859911
AllCCS	[M-H]-	142.0	32859911
AllCCS	[M+Na-2H]-	143.8	32859911
AllCCS	[M+HCOO]-	145.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide	NC(CS(=O)C(Cl)=CCl)C(O)=O	2687.9	Standard polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide	NC(CS(=O)C(Cl)=CCl)C(O)=O	1559.7	Standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide	NC(CS(=O)C(Cl)=CCl)C(O)=O	1967.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TMS,isomer #1	C[Si](C)(C)NC(CS(=O)C(Cl)=CCl)C(=O)O[Si](C)(C)C	1901.0	Semi standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TMS,isomer #1	C[Si](C)(C)NC(CS(=O)C(Cl)=CCl)C(=O)O[Si](C)(C)C	2138.8	Standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TMS,isomer #1	C[Si](C)(C)NC(CS(=O)C(Cl)=CCl)C(=O)O[Si](C)(C)C	2207.9	Standard polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TMS,isomer #2	C[Si](C)(C)N(C(CS(=O)C(Cl)=CCl)C(=O)O)[Si](C)(C)C	2031.4	Semi standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TMS,isomer #2	C[Si](C)(C)N(C(CS(=O)C(Cl)=CCl)C(=O)O)[Si](C)(C)C	2224.5	Standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TMS,isomer #2	C[Si](C)(C)N(C(CS(=O)C(Cl)=CCl)C(=O)O)[Si](C)(C)C	2427.2	Standard polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CS(=O)C(Cl)=CCl)N([Si](C)(C)C)[Si](C)(C)C	2025.9	Semi standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CS(=O)C(Cl)=CCl)N([Si](C)(C)C)[Si](C)(C)C	2314.8	Standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CS(=O)C(Cl)=CCl)N([Si](C)(C)C)[Si](C)(C)C	2142.5	Standard polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CS(=O)C(Cl)=CCl)C(=O)O[Si](C)(C)C(C)(C)C	2358.8	Semi standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CS(=O)C(Cl)=CCl)C(=O)O[Si](C)(C)C(C)(C)C	2680.5	Standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CS(=O)C(Cl)=CCl)C(=O)O[Si](C)(C)C(C)(C)C	2412.8	Standard polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CS(=O)C(Cl)=CCl)C(=O)O)[Si](C)(C)C(C)(C)C	2454.0	Semi standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CS(=O)C(Cl)=CCl)C(=O)O)[Si](C)(C)C(C)(C)C	2700.6	Standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CS(=O)C(Cl)=CCl)C(=O)O)[Si](C)(C)C(C)(C)C	2513.6	Standard polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CS(=O)C(Cl)=CCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2684.7	Semi standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CS(=O)C(Cl)=CCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2999.6	Standard non polar	33892256
S-(1,2-dichlorovinyl)-L-cysteine sulfoxide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CS(=O)C(Cl)=CCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2430.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-(1,2-dichlorovinyl)-L-cysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-2dae1f98bf4e601cc2e2	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(1,2-dichlorovinyl)-L-cysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(1,2-dichlorovinyl)-L-cysteine sulfoxide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(1,2-dichlorovinyl)-L-cysteine sulfoxide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(1,2-dichlorovinyl)-L-cysteine sulfoxide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(1,2-dichlorovinyl)-L-cysteine sulfoxide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	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

Not Available

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 S-(1,2-dichlorovinyl)-L-cysteine sulfoxide (HMDB0257379)

MOL for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

3D MOL for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

3D SDF for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

3D-SDF for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

PDB for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

3D PDB for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

SMILES for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

INCHI for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

Structure for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

3D Structure for HMDB0257379 (S-(1,2-dichlorovinyl)-L-cysteine sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

NMR Spectra