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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-31 22:32:49 UTC

Update Date

2021-09-26 22:48:58 UTC

HMDB ID

HMDB0242510

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid

Description

2-amino-3-[(1,2-dichloroethenyl)sulfanyl]propanoic acid 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 2-amino-3-[(1,2-dichloroethenyl)sulfanyl]propanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2r)-2-amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid 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

Value	Source
2-Amino-3-[(1,2-dichloroethenyl)sulfanyl]propanoate	Generator
2-Amino-3-[(1,2-dichloroethenyl)sulphanyl]propanoate	Generator
2-Amino-3-[(1,2-dichloroethenyl)sulphanyl]propanoic acid	Generator
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoate	Generator
(2R)-2-Amino-3-(1,2-dichloroethenylsulphanyl)propanoate	Generator
(2R)-2-Amino-3-(1,2-dichloroethenylsulphanyl)propanoic acid	Generator

Chemical Formula

C₅H₇Cl₂NO₂S

Average Molecular Weight

216.08

Monoisotopic Molecular Weight

214.957455

IUPAC Name

2-amino-3-[(1,2-dichloroethenyl)sulfanyl]propanoic acid

Traditional Name

2-amino-3-[(1,2-dichloroethenyl)sulfanyl]propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C5H7Cl2NO2S/c6-1-4(7)11-2-3(8)5(9)10/h1,3H,2,8H2,(H,9,10)

InChI Key

PJIHCWJOTSJIPQ-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
Amino acid
Chloroalkene
Haloalkene
Sulfenyl compound
Vinyl halide
Vinyl chloride
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Primary aliphatic amine
Carbonyl group
Amine
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	-1.5	ALOGPS
logP	-0.71	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.57	ChemAxon
pKa (Strongest Basic)	9.05	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	55.62 m³·mol⁻¹	ChemAxon
Polarizability	19.08 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]+	137.094	30932474
DeepCCS	[M-H]-	133.615	30932474
DeepCCS	[M-2H]-	170.842	30932474
DeepCCS	[M+Na]+	145.958	30932474
AllCCS	[M+H]+	141.7	32859911
AllCCS	[M+H-H2O]+	138.2	32859911
AllCCS	[M+NH4]+	144.9	32859911
AllCCS	[M+Na]+	145.8	32859911
AllCCS	[M-H]-	141.6	32859911
AllCCS	[M+Na-2H]-	143.7	32859911
AllCCS	[M+HCOO]-	146.0	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CSC(Cl)=CCl	1680.8	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CSC(Cl)=CCl	1654.9	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CSC(Cl)=CCl	2646.6	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TMS,isomer #2	C[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O	1783.4	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TMS,isomer #2	C[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O	1621.5	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TMS,isomer #2	C[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O	2554.8	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TMS,isomer #1	C[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O[Si](C)(C)C	1784.6	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TMS,isomer #1	C[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O[Si](C)(C)C	1733.9	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TMS,isomer #1	C[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O[Si](C)(C)C	2149.1	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TMS,isomer #2	C[Si](C)(C)N(C(CSC(Cl)=CCl)C(=O)O)[Si](C)(C)C	1959.7	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TMS,isomer #2	C[Si](C)(C)N(C(CSC(Cl)=CCl)C(=O)O)[Si](C)(C)C	1819.2	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TMS,isomer #2	C[Si](C)(C)N(C(CSC(Cl)=CCl)C(=O)O)[Si](C)(C)C	2357.0	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CSC(Cl)=CCl)N([Si](C)(C)C)[Si](C)(C)C	1934.4	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CSC(Cl)=CCl)N([Si](C)(C)C)[Si](C)(C)C	1890.3	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CSC(Cl)=CCl)N([Si](C)(C)C)[Si](C)(C)C	2084.3	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CSC(Cl)=CCl	1927.0	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CSC(Cl)=CCl	1896.8	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CSC(Cl)=CCl	2735.2	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O	2035.9	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O	1884.1	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O	2632.1	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O[Si](C)(C)C(C)(C)C	2245.9	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O[Si](C)(C)C(C)(C)C	2220.1	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CSC(Cl)=CCl)C(=O)O[Si](C)(C)C(C)(C)C	2350.9	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CSC(Cl)=CCl)C(=O)O)[Si](C)(C)C(C)(C)C	2344.4	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CSC(Cl)=CCl)C(=O)O)[Si](C)(C)C(C)(C)C	2255.9	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CSC(Cl)=CCl)C(=O)O)[Si](C)(C)C(C)(C)C	2444.3	Standard polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CSC(Cl)=CCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2566.2	Semi standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CSC(Cl)=CCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2530.5	Standard non polar	33892256
(2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CSC(Cl)=CCl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2381.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-5f58a120748f77b70acb	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid 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 - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid 10V, Positive-QTOF	splash10-0002-0910000000-955d84b3090ac397264f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid 20V, Positive-QTOF	splash10-0g6r-6900000000-3e44dbbfaedc48cc964d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid 40V, Positive-QTOF	splash10-004l-9500000000-b02409377c6950b00ce8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid 10V, Negative-QTOF	splash10-00di-4910000000-08d9a08334932fa548f2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid 20V, Negative-QTOF	splash10-001i-9100000000-fe488010114192ba6321	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid 40V, Negative-QTOF	splash10-001i-9000000000-23104f9af9bae2053267	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)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

24190

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25967

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 (2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid (HMDB0242510)

MOL for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

3D MOL for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

3D SDF for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

3D-SDF for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

PDB for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

3D PDB for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

SMILES for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

INCHI for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

Structure for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

3D Structure for HMDB0242510 ((2R)-2-Amino-3-(1,2-dichloroethenylsulfanyl)propanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra