Showing Compound 3-(Methylthio)alanine (FDB012676)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:18 UTC

Update date

2019-11-26 03:07:22 UTC

Primary ID

FDB012676

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-(Methylthio)alanine

Description

Occurs in all members of the genus Allium, at least two genera of Brassicaceae family (Brassica and Raphanus) and sporadically in the families Compositae, Leguminosae and Umbelliferae. Found in kidney bean seeds (Phaseolus vulgaris) Methylcysteine is one of the identified number of bioactive substances in garlic that are water soluble. (PMID 16484549); It has been suggested that the use of these organosulfur agents derived from garlic could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases. (PMID 15161248); It may also exert some chemopreventive effects on chemical carcinogenesis. However, it should be borne in mind that may also demonstrate promotion potential, depending on the organ examined. (PMID 9591199). S-Methylcystein is a biomarker for the consumption of dried and cooked beans.

CAS Number

1187-84-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
S-Methylcysteine, (DL-cys)-isomer	MeSH
S-11C-Methyl-L-cysteine	MeSH
S-Methylcysteine, (L-cys)-isomer	MeSH
S-Methylcysteine, hydrochloride, (L-cys)-isomer	MeSH
(R)-2-Amino-3-(methylmercapto)propionic acid	biospider
3-(methylthio)-L-(8CI)alanine	biospider
3-(methylthio)-L-alanine	biospider
3-(Methylthio)alanine	db_source
Acm-thiopropionate	biospider
Acm-thiopropionic acid	biospider
Alanine, 3-(methylthio)-, L-	biospider
Alanine, 3-(methylthio)-, L- (8CI)	biospider
CYM	biospider
Cysteine, s-methyl-	biospider
L-aspartic acid dimethyl ester	biospider
L-cysteine, s-methyl-	biospider
L-Cysteine, S-methyl- (9CI)	biospider
L-methylcysteine	biospider
Methylcysteine, l-	biospider
S-acetamidomethyl-deamino-cysteine	biospider
S-methyl-(9CI)-L-cysteine	biospider
S-methyl-cysteine	biospider
S-methyl-DL-cysteine	biospider
S-methyl-l-cysteine	biospider
S-Methylcysteine	db_source
SMC	biospider

Predicted Properties

Property	Value	Source
Water Solubility	65.8 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.4	ChemAxon
logS	-0.31	ALOGPS
pKa (Strongest Acidic)	2.44	ChemAxon
pKa (Strongest Basic)	9.15	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	3	ChemAxon
Refractivity	32.87 m³·mol⁻¹	ChemAxon
Polarizability	13.56 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

C4H9NO2S

IUPAC name

2-amino-3-(methylsulfanyl)propanoic acid

InChI Identifier

InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)

InChI Key

IDIDJDIHTAOVLG-UHFFFAOYSA-N

Isomeric SMILES

CSCC(N)C(O)=O

Average Molecular Weight

135.185

Monoisotopic Molecular Weight

135.035399227

Classification

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
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Sulfenyl compound
Dialkylthioether
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

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 35.54%; H 6.71%; N 10.36%; O 23.67%; S 23.72%	DFC
Melting Point	Mp 234-236 dec. (207-211°)	DFC
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	[a]26D -32 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9700000000-8f3d25ac52279c092856	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9200000000-b405850a71df669cec12	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9000000000-ace8060e79e2568e8fd6	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9200000000-0100ccbfcee39a28f73d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000b-9000000000-77f7473e8f64b00cba29	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-5f83877d00d54983d86c	2016-08-03	View Spectrum