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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:00:05 UTC

Update Date

2023-02-21 17:26:41 UTC

HMDB ID

HMDB0038669

Secondary Accession Numbers

HMDB38669

Metabolite Identification

Common Name

S-(Allylthio)-L-cysteine

Description

S-(Allylthio)-L-cysteine 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. S-(Allylthio)-L-cysteine has been detected, but not quantified in, several different foods, such as garlics (Allium sativum), garden onion (var.), welsh onions (Allium fistulosum), onion-family vegetables, and garden onions (Allium cepa). This could make S-(allylthio)-L-cysteine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on S-(Allylthio)-L-cysteine.

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-(prop-2-en-1-yldisulfanyl)propanoate	Generator
2-Amino-3-(prop-2-en-1-yldisulphanyl)propanoate	Generator
2-Amino-3-(prop-2-en-1-yldisulphanyl)propanoic acid	Generator

Chemical Formula

C₆H₁₁NO₂S₂

Average Molecular Weight

193.287

Monoisotopic Molecular Weight

193.023119981

IUPAC Name

2-amino-3-(prop-2-en-1-yldisulfanyl)propanoic acid

Traditional Name

2-amino-3-(prop-2-en-1-yldisulfanyl)propanoic acid

CAS Registry Number

2281-22-3

SMILES

NC(CSSCC=C)C(O)=O

InChI Identifier

InChI=1S/C6H11NO2S2/c1-2-3-10-11-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)

InChI Key

WYQZZUUUOXNSCS-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
Organic disulfide
Allyl sulfur compound
Amino acid
Dialkyldisulfide
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfenyl compound
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
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)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	187 - 188 °C	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
Water Solubility	2.48 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.6	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.26	ChemAxon
pKa (Strongest Basic)	9.04	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	6	ChemAxon
Refractivity	50.14 m³·mol⁻¹	ChemAxon
Polarizability	19.5 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
DarkChem	[M+H]+	143.562	31661259
DarkChem	[M-H]-	134.764	31661259
DeepCCS	[M+H]+	136.506	30932474
DeepCCS	[M-H]-	133.66	30932474
DeepCCS	[M-2H]-	170.423	30932474
DeepCCS	[M+Na]+	145.224	30932474
AllCCS	[M+H]+	141.2	32859911
AllCCS	[M+H-H2O]+	137.7	32859911
AllCCS	[M+NH4]+	144.5	32859911
AllCCS	[M+Na]+	145.4	32859911
AllCCS	[M-H]-	140.9	32859911
AllCCS	[M+Na-2H]-	143.0	32859911
AllCCS	[M+HCOO]-	145.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.83 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4584 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	233.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-(Allylthio)-L-cysteine	NC(CSSCC=C)C(O)=O	2843.2	Standard polar	33892256
S-(Allylthio)-L-cysteine	NC(CSSCC=C)C(O)=O	1545.2	Standard non polar	33892256
S-(Allylthio)-L-cysteine	NC(CSSCC=C)C(O)=O	1743.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-(Allylthio)-L-cysteine,1TMS,isomer #1	C=CCSSCC(N)C(=O)O[Si](C)(C)C	1695.7	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,1TMS,isomer #2	C=CCSSCC(N[Si](C)(C)C)C(=O)O	1746.7	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,2TMS,isomer #1	C=CCSSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1781.4	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,2TMS,isomer #1	C=CCSSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1774.9	Standard non polar	33892256
S-(Allylthio)-L-cysteine,2TMS,isomer #2	C=CCSSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1885.5	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,2TMS,isomer #2	C=CCSSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1844.3	Standard non polar	33892256
S-(Allylthio)-L-cysteine,3TMS,isomer #1	C=CCSSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1899.8	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,3TMS,isomer #1	C=CCSSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1906.2	Standard non polar	33892256
S-(Allylthio)-L-cysteine,1TBDMS,isomer #1	C=CCSSCC(N)C(=O)O[Si](C)(C)C(C)(C)C	1924.1	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,1TBDMS,isomer #2	C=CCSSCC(N[Si](C)(C)C(C)(C)C)C(=O)O	1962.1	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,2TBDMS,isomer #1	C=CCSSCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2218.5	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,2TBDMS,isomer #1	C=CCSSCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2200.5	Standard non polar	33892256
S-(Allylthio)-L-cysteine,2TBDMS,isomer #2	C=CCSSCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2316.4	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,2TBDMS,isomer #2	C=CCSSCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2265.6	Standard non polar	33892256
S-(Allylthio)-L-cysteine,3TBDMS,isomer #1	C=CCSSCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2570.9	Semi standard non polar	33892256
S-(Allylthio)-L-cysteine,3TBDMS,isomer #1	C=CCSSCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2512.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-(Allylthio)-L-cysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-ab9294e05198f9aab008	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(Allylthio)-L-cysteine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9410000000-ae245d8790692b349471	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(Allylthio)-L-cysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(Allylthio)-L-cysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(Allylthio)-L-cysteine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(Allylthio)-L-cysteine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(Allylthio)-L-cysteine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	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 - S-(Allylthio)-L-cysteine 10V, Positive-QTOF	splash10-002e-3900000000-4876a22f2f5ba0f6b534	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 20V, Positive-QTOF	splash10-006x-9700000000-f5a09d9642a467e1ab95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 40V, Positive-QTOF	splash10-00dl-9100000000-90a11e14655d14dd0759	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 10V, Negative-QTOF	splash10-0f6x-2900000000-46e79a840d9788690d1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 20V, Negative-QTOF	splash10-00di-9500000000-67ea0c44aca85ab5935f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 40V, Negative-QTOF	splash10-00dr-9200000000-9ed68e236dd62b90a9d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 10V, Positive-QTOF	splash10-00di-3900000000-ca59010d3f9780383982	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 20V, Positive-QTOF	splash10-00di-9300000000-97c1a9e6c247b7c154d3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 40V, Positive-QTOF	splash10-022c-9000000000-f47f398ed4b7f5a88204	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 10V, Negative-QTOF	splash10-00di-3900000000-dbab91aedbd0966c5178	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 20V, Negative-QTOF	splash10-00di-9200000000-e2303ad560ff9000005c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(Allylthio)-L-cysteine 40V, Negative-QTOF	splash10-03di-9000000000-e2cac89c0f3fb508329c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB018068

KNApSAcK ID

Not Available

Chemspider ID

8012745

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9837024

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for S-(Allylthio)-L-cysteine (HMDB0038669)

MOL for HMDB0038669 (S-(Allylthio)-L-cysteine)

3D MOL for HMDB0038669 (S-(Allylthio)-L-cysteine)

3D SDF for HMDB0038669 (S-(Allylthio)-L-cysteine)

3D-SDF for HMDB0038669 (S-(Allylthio)-L-cysteine)

PDB for HMDB0038669 (S-(Allylthio)-L-cysteine)

3D PDB for HMDB0038669 (S-(Allylthio)-L-cysteine)

SMILES for HMDB0038669 (S-(Allylthio)-L-cysteine)

INCHI for HMDB0038669 (S-(Allylthio)-L-cysteine)

Structure for HMDB0038669 (S-(Allylthio)-L-cysteine)

3D Structure for HMDB0038669 (S-(Allylthio)-L-cysteine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra