AFCDB: S-Methylcysteine sulfoxide (FDB000534)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:36 UTC

Update date

2020-02-24 19:10:09 UTC

Primary ID

FDB000534

Secondary Accession Numbers

FDB000535

Chemical Information

FooDB Name

S-Methylcysteine sulfoxide

Description

(s)c(s)s-s-methylcysteine sulfoxide, also known as methiin, (dl-ala)-isomer or kale anemia factor, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon) (s)c(s)s-s-methylcysteine sulfoxide is soluble (in water) and a moderately acidic compound (based on its pKa). (s)c(s)s-s-methylcysteine sulfoxide can be found in brassicas, garden onion, and onion-family vegetables, which makes (s)c(s)s-s-methylcysteine sulfoxide a potential biomarker for the consumption of these food products.

CAS Number

32726-14-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted 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

Chemical Formula

C4H9NO3S

IUPAC name

2-amino-3-methanesulfinylpropanoic acid

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

Isomeric SMILES

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

Average Molecular Weight

151.184

Monoisotopic Molecular Weight

151.030313849

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	liquid
Physical Description	Not Available
Mass Composition	C 31.78%; H 6.00%; N 9.26%; O 31.75%; S 21.21%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	S-Methylcysteine sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00du-9100000000-473920cb756c30846723	Spectrum
Predicted GC-MS	S-Methylcysteine sulfoxide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05cf-9300000000-17adc95a38f45ac85bec	Spectrum
Predicted GC-MS	S-Methylcysteine sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-Methylcysteine sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-Methylcysteine sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-Methylcysteine sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-Methylcysteine sulfoxide, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-Methylcysteine sulfoxide, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0w29-8900000000-708d42281d8ea6475839	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-789d499df8b51945a71b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-46f1ce4b0ccd17913852	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-433cb4a770ae8f69c615	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-9ae7204cc64a4ada6c6b	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pc0-1900000000-be560bcb3c2bc917c359	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-6900000000-02b3d992681a9df63581	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-5437d8547afb32f87afc	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zmi-9800000000-8e311231b75fa3f22035	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9100000000-505a5073b21dee92709c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-6db85bfed0c07b4e9e8d	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BDH53-E:BDH53-E

EAFUS ID

Not Available

Dr. Duke ID

S-METHYL-CYSTEINE-SULFOXIDE|METHIIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hypercholesterolemic			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

S-Methylcysteine sulfoxide (FDB000534)

Structure for FDB000534 (S-Methylcysteine sulfoxide)