S-Methyl-L-cysteine - 10mM in Water , CAS No.1187-84-4

CAS: 1187-84-4 Cat. No.: S420826 Molecular Weight: 135.18 Beilstein Registry Number: 1721675 EC Number: 214-701-6

GRADE & PURITY 10mM in Water

Synonyms

EINECS 243-203-1 | L-S-Methyl-cysteine | AKOS000275785 | CHEBI:45658 | (2R)-2-azaniumyl-3-(methylsulfanyl)propanoate | L-Methylcysteine | GS-3468 | Q27093260 | 3-(METHYLTHIO)ALANINE | L-Cysteine, S-methyl- | MFCD00002612 | (R)-2-Amino-3-(methylmercapto)pr

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

substrate for methionine sulfoxide reductase A

Specifications

Synonyms

EINECS 243-203-1 | L-S-Methyl-cysteine | AKOS000275785 | CHEBI:45658 | (2R)-2-azaniumyl-3-(methylsulfanyl)propanoate | L-Methylcysteine | GS-3468 | Q27093260 | 3-(METHYLTHIO)ALANINE | L-Cysteine, S-methyl- | MFCD00002612 | (R)-2-Amino-3-(methylmercapto)pr

Specifications & Purity

10mM in Water

Biochemical and Physiological Mechanisms

S-Methyl-L-cysteine (SMLC) is a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA). SMLC is naturally present in garlic, cabbage, and turnips and has been studied as a theurapeutic for neurodegenerative disea

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CSCC(C(=O)O)N
• IUPAC Name: (2R)-2-amino-3-methylsulfanylpropanoic acid
• InChIKey: IDIDJDIHTAOVLG-VKHMYHEASA-N
• INCHI: 1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
• Isomeric SMILES: CSC[C@@H](C(=O)O)N
• WGK Germany: 3
• Molecular Weight: 135.18
• Beilstein: 1721675
• Reaxy-Rn: 2038947
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2038947&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Cysteine and derivatives
              • Level8 L-cysteine-S-conjugates

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Cysteine and derivatives
• Direct Parent: L-cysteine-S-conjugates
• Alternative Parents: L-alpha-amino acids Amino acids Sulfenyl compounds Monocarboxylic acids and derivatives Dialkylthioethers Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: L-cysteine-s-conjugate - Alpha-amino acid - L-alpha-amino acid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Thioether - Sulfenyl compound - Dialkylthioether - Carbonyl group - Amine - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Primary aliphatic amine - Organic oxygen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxide - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
• External Descriptors: S-alkyl-L-cysteine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

HeLa (62764 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KIF11 Tchem Kinesin-like protein 1 (1720 Activities)

Discover Target: KIF11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc1a5 Amino acid transporter (271 Activities)

Discover Target: Slc1a5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: -30 ° (C=2, H2O)
• Melt Point(°C): 240°C
• Molecular Weight: 135.190 g/mol
• XLogP3: -2.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 135.035 Da
• Monoisotopic Mass: 135.035 Da
• Topological Polar Surface Area: 88.600 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 86.100
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jing Nie, Rui Weng, Chunlin Li, Xiuhua Liu, Fang Wang, Karyne M. Rogers, Yongzhong Qian, Yongzhi Zhang, Yuwei Yuan.  (2022)  Chemometric origin classification of Chinese garlic using sulfur-containing compounds, assisted by stable isotopes and bioelements.  FOOD CHEMISTRY,      [PMID:35759834] [10.1016/j.foodchem.2022.133557]