Methionine sulfoximine

Details

• Internal ID: 8246a68e-831c-4754-bc25-91c04af42264
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids
• IUPAC Name: 2-amino-4-(methylsulfonimidoyl)butanoic acid
• SMILES (Canonical): CS(=N)(=O)CCC(C(=O)O)N
• SMILES (Isomeric): CS(=N)(=O)CCC(C(=O)O)N
• InChI: InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)
• InChI Key: SXTAYKAGBXMACB-UHFFFAOYSA-N
• Popularity: 1,553 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₁₂N₂O₃S
• Molecular Weight: 180.23 g/mol
• Exact Mass: 180.05686342 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 2-Amino-4-(S-methylsulfonimidoyl)butanoic acid
• 1982-67-8
• DL-Methionine-DL-sulfoximine
• 2-Amino-4-(S-methylsulphonimidoyl)butyric acid
• 2-amino-4-(methylsulfonimidoyl)butanoic acid
• CHEBI:47833
• l-methionine-dl-sulfoximine
• (R)-L-S-(3-Amino-3-carboxypropyl)-s-methylsulfoximine
• Methionine-rs-sulfoximine, L-
• CCRIS 5096
• Methionine-DL-sulfoximine, DL-
• L-Methionine [S]-Sulfoximine
• EINECS 217-845-8
• (2S)-2-AMINO-4-(METHYLSULFONIMIDOYL)BUTANOIC ACID
• Butanoic acid, 2-amino-4-(S-methylsulfonimidoyl)-
• DL-banthionine-DL-sulfoximine
• AI3-62723
• DL-METHIONINE SULFOXIMINE
• L-Methionine-RS-sulfoximine
• DL-(3-Amino-3-carboxypropyl) methyl sulfoximine
• DL-Methionine DL-sulfoximine
• SCHEMBL187873
• L -S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine
• CHEMBL1615096
• Sulfoximine, S-(3-amino-3-carboxypropyl)-S-methyl-, DL-
• SXTAYKAGBXMACB-UHFFFAOYSA-N
• DTXSID201031266
• NSC49169
• CCG-42326
• MFCD00063094
• NSC-49169
• AKOS005171800
• SB33993
• BB 0260911
• CS-0449453
• FT-0627959
• FT-0671137
• FT-0671138
• FT-0694474
• 2-Amino-4-(S-methylsulfonimidoyl)butanoicacid
• EN300-373833
• 2-Amino-4-(S-methylsulfonimidoyl)-Butanoic acid
• AE-641/01924064
• J-014271
• SR-01000632335-1
• W-109734
• Q27120816
• S-(3-Amino-3-carboxypropyl)-S-methyl-DL-Sulfoximine
• S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine, 9CI
• 2-amino-4-[imino(methyl)oxo-lambda6-sulfanyl]butanoic acid
• Butanoic acid, 2-amino-4-(S-methylsulfonimidoyl)- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7672	76.72%
Caco-2	-	0.8902	89.02%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5449	54.49%
OATP2B1 inhibitior	-	0.8471	84.71%
OATP1B1 inhibitior	+	0.9674	96.74%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9398	93.98%
P-glycoprotein inhibitior	-	0.9799	97.99%
P-glycoprotein substrate	-	0.9620	96.20%
CYP3A4 substrate	-	0.7115	71.15%
CYP2C9 substrate	+	0.5975	59.75%
CYP2D6 substrate	-	0.7660	76.60%
CYP3A4 inhibition	-	0.9734	97.34%
CYP2C9 inhibition	-	0.9168	91.68%
CYP2C19 inhibition	-	0.9135	91.35%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9850	98.50%
CYP inhibitory promiscuity	-	0.9942	99.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5942	59.42%
Carcinogenicity (trinary)	Non-required	0.6412	64.12%
Eye corrosion	-	0.9664	96.64%
Eye irritation	-	0.8269	82.69%
Skin irritation	-	0.7900	79.00%
Skin corrosion	-	0.9143	91.43%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7622	76.22%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8413	84.13%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8432	84.32%
Acute Oral Toxicity (c)	III	0.5662	56.62%
Estrogen receptor binding	-	0.8571	85.71%
Androgen receptor binding	-	0.8622	86.22%
Thyroid receptor binding	-	0.8929	89.29%
Glucocorticoid receptor binding	-	0.7802	78.02%
Aromatase binding	-	0.9055	90.55%
PPAR gamma	-	0.8310	83.10%
Honey bee toxicity	-	0.9565	95.65%
Biodegradation	+	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	-	0.5104	51.04%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	15.8 nM	Potency	via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	158.5 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	25.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	94.76%	92.29%
CHEMBL2581	P07339	Cathepsin D	92.26%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.07%	95.17%
CHEMBL236	P41143	Delta opioid receptor	86.87%	99.35%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.66%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.14%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.73%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.36%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	80.49%	91.19%

Plants that contains it

• Cnestis polyphylla

Cross-Links

• PubChem: 16118
• LOTUS: LTS0193763
• wikiData: Q27120816