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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:23 UTC

Update Date

2022-03-07 02:52:09 UTC

HMDB ID

HMDB0029432

Secondary Accession Numbers

HMDB29432

Metabolite Identification

Common Name

(S)C(S)S-S-Methylcysteine sulfoxide

Description

S-Methylcysteine sulfoxide 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). S-Methylcysteine sulfoxide has been detected, but not quantified in, several different foods, such as cabbages (Brassica oleracea var. capitata), garden onions (Allium cepa), soft-necked garlics (Allium sativum L. var. sativum), and white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.). This could make S-methylcysteine sulfoxide a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on S-Methylcysteine sulfoxide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
S-Methylcysteine sulphoxide	Generator
MethyIIn, pyrolyzate	HMDB
S-Methylcysteine sulfoxide	MeSH, HMDB
Kale anemia factor	MeSH, HMDB
S-Methyl-L-cysteinesulfoxide	MeSH, HMDB
Methiin	MeSH, HMDB
Methiin, (L-ala)-(S)-isomer	MeSH, HMDB
Methiin, (DL-ala)-isomer	MeSH, HMDB
Methiin, (L-ala)-(R)-isomer	MeSH, HMDB
Methiin, (L-ala)-isomer	MeSH, HMDB
2-Amino-3-methanesulfinylpropanoate	Generator, HMDB
2-Amino-3-methanesulphinylpropanoate	Generator, HMDB
2-Amino-3-methanesulphinylpropanoic acid	Generator, HMDB
(S)C(S)S-S-Methylcysteine sulphoxide	Generator

Chemical Formula

C₄H₉NO₃S

Average Molecular Weight

151.184

Monoisotopic Molecular Weight

151.030313849

IUPAC Name

2-amino-3-methanesulfinylpropanoic acid

Traditional Name

2-amino-3-methanesulfinylpropanoic acid

CAS Registry Number

32726-14-0

SMILES

CS(=O)CC(N)C(O)=O

InChI Identifier

InChI=1S/C4H9NO3S/c1-9(8)2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)

InChI Key

ZZLHPCSGGOGHFW-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
Sulfinyl compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 °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	50.4 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-4.6	ChemAxon
logS	-0.48	ALOGPS
pKa (Strongest Acidic)	1.61	ChemAxon
pKa (Strongest Basic)	8.45	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	3	ChemAxon
Refractivity	34.59 m³·mol⁻¹	ChemAxon
Polarizability	14.06 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]+	132.881	31661259
DarkChem	[M-H]-	126.127	31661259
DeepCCS	[M+H]+	127.344	30932474
DeepCCS	[M-H]-	124.407	30932474
DeepCCS	[M-2H]-	161.002	30932474
DeepCCS	[M+Na]+	135.93	30932474
AllCCS	[M+H]+	133.5	32859911
AllCCS	[M+H-H2O]+	129.6	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.2	32859911
AllCCS	[M-H]-	128.9	32859911
AllCCS	[M+Na-2H]-	131.7	32859911
AllCCS	[M+HCOO]-	134.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)C(S)S-S-Methylcysteine sulfoxide	CS(=O)CC(N)C(O)=O	2541.4	Standard polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide	CS(=O)CC(N)C(O)=O	1279.8	Standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide	CS(=O)CC(N)C(O)=O	1566.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)C(S)S-S-Methylcysteine sulfoxide,1TMS,isomer #1	CS(=O)CC(N)C(=O)O[Si](C)(C)C	1384.3	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,1TMS,isomer #2	CS(=O)CC(N[Si](C)(C)C)C(=O)O	1460.9	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,2TMS,isomer #1	CS(=O)CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1522.3	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,2TMS,isomer #1	CS(=O)CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1804.8	Standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,2TMS,isomer #2	CS(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1661.8	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,2TMS,isomer #2	CS(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1814.9	Standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,3TMS,isomer #1	CS(=O)CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1689.8	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,3TMS,isomer #1	CS(=O)CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1945.7	Standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,1TBDMS,isomer #1	CS(=O)CC(N)C(=O)O[Si](C)(C)C(C)(C)C	1639.2	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,1TBDMS,isomer #2	CS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O	1730.5	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,2TBDMS,isomer #1	CS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1969.2	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,2TBDMS,isomer #1	CS(=O)CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2416.8	Standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,2TBDMS,isomer #2	CS(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2104.4	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,2TBDMS,isomer #2	CS(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2311.8	Standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,3TBDMS,isomer #1	CS(=O)CC(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	2344.1	Semi standard non polar	33892256
(S)C(S)S-S-Methylcysteine sulfoxide,3TBDMS,isomer #1	CS(=O)CC(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	2726.6	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)C(S)S-S-Methylcysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00du-9100000000-473920cb756c30846723	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide GC-MS (1 TMS) - 70eV, Positive	splash10-05cf-9300000000-17adc95a38f45ac85bec	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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)C(S)S-S-Methylcysteine sulfoxide 10V, Positive-QTOF	splash10-0pc0-1900000000-be560bcb3c2bc917c359	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 20V, Positive-QTOF	splash10-0a4i-6900000000-02b3d992681a9df63581	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 40V, Positive-QTOF	splash10-0006-9000000000-5437d8547afb32f87afc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 10V, Negative-QTOF	splash10-0w29-8900000000-708d42281d8ea6475839	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 20V, Negative-QTOF	splash10-03di-9000000000-789d499df8b51945a71b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 40V, Negative-QTOF	splash10-03di-9000000000-46f1ce4b0ccd17913852	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 10V, Negative-QTOF	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 20V, Negative-QTOF	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 40V, Negative-QTOF	splash10-0006-9000000000-9ae7204cc64a4ada6c6b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 10V, Positive-QTOF	splash10-0zmi-9800000000-8e311231b75fa3f22035	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 20V, Positive-QTOF	splash10-006x-9100000000-505a5073b21dee92709c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)C(S)S-S-Methylcysteine sulfoxide 40V, Positive-QTOF	splash10-03di-9000000000-6db85bfed0c07b4e9e8d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart 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

FDB000534

KNApSAcK ID

Not Available

Chemspider ID

74136

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25202909

PDB ID

Not Available

ChEBI ID

137271

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)C(S)S-S-Methylcysteine sulfoxide (HMDB0029432)

MOL for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

3D MOL for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

3D SDF for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

3D-SDF for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

PDB for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

3D PDB for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

SMILES for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

INCHI for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

Structure for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

3D Structure for HMDB0029432 ((S)C(S)S-S-Methylcysteine sulfoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra