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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:50:41 UTC

Update Date

2021-09-26 22:54:28 UTC

HMDB ID

HMDB0245792

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-[(2,2-Dichlorovinyl)thio]-L-alanine

Description

3-[(2,2-Dichlorovinyl)thio]-L-alanine belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on 3-[(2,2-Dichlorovinyl)thio]-L-alanine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-[(2,2-dichlorovinyl)thio]-l-alanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-[(2,2-Dichlorovinyl)thio]-L-alanine 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 NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₅H₇Cl₂NO₂S

Average Molecular Weight

216.08

Monoisotopic Molecular Weight

214.957455

IUPAC Name

2-amino-3-[(2,2-dichloroethenyl)sulfanyl]propanoic acid

Traditional Name

2-amino-3-[(2,2-dichloroethenyl)sulfanyl]propanoic acid

CAS Registry Number

Not Available

SMILES

NC(CSC=C(Cl)Cl)C(O)=O

InChI Identifier

InChI=1S/C5H7Cl2NO2S/c6-4(7)2-11-1-3(8)5(9)10/h2-3H,1,8H2,(H,9,10)

InChI Key

HTUPGSGHOGPTAF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic 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	-1.4	ALOGPS
logP	-1.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.53	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.21 m³·mol⁻¹	ChemAxon
Polarizability	18.79 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]+	134.1	30932474
DeepCCS	[M-H]-	130.691	30932474
DeepCCS	[M-2H]-	167.736	30932474
DeepCCS	[M+Na]+	142.887	30932474
AllCCS	[M+H]+	141.8	32859911
AllCCS	[M+H-H2O]+	138.4	32859911
AllCCS	[M+NH4]+	145.0	32859911
AllCCS	[M+Na]+	145.9	32859911
AllCCS	[M-H]-	141.9	32859911
AllCCS	[M+Na-2H]-	143.9	32859911
AllCCS	[M+HCOO]-	146.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-[(2,2-Dichlorovinyl)thio]-L-alanine	NC(CSC=C(Cl)Cl)C(O)=O	2557.4	Standard polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine	NC(CSC=C(Cl)Cl)C(O)=O	1544.1	Standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine	NC(CSC=C(Cl)Cl)C(O)=O	1824.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TMS,isomer #1	C[Si](C)(C)NC(CSC=C(Cl)Cl)C(=O)O[Si](C)(C)C	1775.2	Semi standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TMS,isomer #1	C[Si](C)(C)NC(CSC=C(Cl)Cl)C(=O)O[Si](C)(C)C	1757.9	Standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TMS,isomer #1	C[Si](C)(C)NC(CSC=C(Cl)Cl)C(=O)O[Si](C)(C)C	2239.1	Standard polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TMS,isomer #2	C[Si](C)(C)N(C(CSC=C(Cl)Cl)C(=O)O)[Si](C)(C)C	1922.3	Semi standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TMS,isomer #2	C[Si](C)(C)N(C(CSC=C(Cl)Cl)C(=O)O)[Si](C)(C)C	1842.9	Standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TMS,isomer #2	C[Si](C)(C)N(C(CSC=C(Cl)Cl)C(=O)O)[Si](C)(C)C	2463.2	Standard polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CSC=C(Cl)Cl)N([Si](C)(C)C)[Si](C)(C)C	1913.5	Semi standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CSC=C(Cl)Cl)N([Si](C)(C)C)[Si](C)(C)C	1910.4	Standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CSC=C(Cl)Cl)N([Si](C)(C)C)[Si](C)(C)C	2156.4	Standard polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CSC=C(Cl)Cl)C(=O)O[Si](C)(C)C(C)(C)C	2240.2	Semi standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CSC=C(Cl)Cl)C(=O)O[Si](C)(C)C(C)(C)C	2245.9	Standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CSC=C(Cl)Cl)C(=O)O[Si](C)(C)C(C)(C)C	2414.1	Standard polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CSC=C(Cl)Cl)C(=O)O)[Si](C)(C)C(C)(C)C	2331.5	Semi standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CSC=C(Cl)Cl)C(=O)O)[Si](C)(C)C(C)(C)C	2274.0	Standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CSC=C(Cl)Cl)C(=O)O)[Si](C)(C)C(C)(C)C	2518.8	Standard polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CSC=C(Cl)Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2567.5	Semi standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CSC=C(Cl)Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2542.9	Standard non polar	33892256
3-[(2,2-Dichlorovinyl)thio]-L-alanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CSC=C(Cl)Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2437.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-1b2f41738086c4d43c79	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 3-[(2,2-Dichlorovinyl)thio]-L-alanine 10V, Positive-QTOF	splash10-004j-0910000000-934117b7dbcb63d64717	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine 20V, Positive-QTOF	splash10-0v6u-4900000000-90a310e2e0886328fbc5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine 40V, Positive-QTOF	splash10-003u-9300000000-ab2ab4176d53a3d7d941	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine 10V, Negative-QTOF	splash10-03di-1690000000-1630049b9d0375b09d68	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine 20V, Negative-QTOF	splash10-001i-9100000000-55a5a51b3492a9df3bdb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-[(2,2-Dichlorovinyl)thio]-L-alanine 40V, Negative-QTOF	splash10-003r-9800000000-84e2e432e2a8a8888686	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C 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	¹³C NMR Spectrum (1D, 200 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, 300 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	¹H NMR Spectrum (1D, 400 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, 500 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	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

26503590

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53462812

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 3-[(2,2-Dichlorovinyl)thio]-L-alanine (HMDB0245792)

MOL for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

3D MOL for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

3D SDF for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

3D-SDF for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

PDB for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

3D PDB for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

SMILES for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

INCHI for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

Structure for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

3D Structure for HMDB0245792 (3-[(2,2-Dichlorovinyl)thio]-L-alanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra