Vitamin U

Details

• Internal ID: 4766634c-6b47-4109-a28c-5d5d69b5077b
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Methionine and derivatives
• IUPAC Name: (2S)-2-amino-4-dimethylsulfoniobutanoate
• SMILES (Canonical): C[S+](C)CCC(C(=O)[O-])N
• SMILES (Isomeric): C[S+](C)CC[C@@H](C(=O)[O-])N
• InChI: InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/t5-/m0/s1
• InChI Key: YDBYJHTYSHBBAU-YFKPBYRVSA-N
• Popularity: 182 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₃NO₂S
• Molecular Weight: 163.24 g/mol
• Exact Mass: 163.06669983 g/mol
• Topological Polar Surface Area (TPSA): 67.20 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.67
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• S-methyl-L-methioninate
• Vitamin U
• S-Methyl-L-methionine
• Methyl sulfonium methionine
• Cu Vita-U
• Methionine, methyl sulfonium
• 4727-40-6
• S-Methylmethionine sulfonium salt
• S-methylmethionine
• UNII-3485Y39925
• (2S)-2-amino-4-dimethylsulfoniobutanoate
• CHEBI:67050
• 3485Y39925
• Sulfonium, ((3S)-3-amino-3-carboxypropyl)dimethyl-, inner salt
• Sulfonium, (3-amino-3-carboxypropyl)dimethyl-, inner salt, (S)-
• (2S)-2-amino-4-(dimethylsulfonio)butanoate
• VITAMIN U [WHO-DD]
• S-METHYLMETHIONINE ION
• SCHEMBL398004
• METHYLMETHIONINE [INCI]
• S-METHYLMETHIONINE [MI]
• CHEMBL2074824
• DTXSID401314761
• [(3S)-3-Amino-3-carboxypropyl]dimethyl sulfonium inner salt

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9741	97.41%
Caco-2	-	0.8599	85.99%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Lysosomes	0.8073	80.73%
OATP2B1 inhibitior	-	0.8457	84.57%
OATP1B1 inhibitior	+	0.9534	95.34%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.9609	96.09%
P-glycoprotein inhibitior	-	0.9847	98.47%
P-glycoprotein substrate	-	0.9490	94.90%
CYP3A4 substrate	-	0.6651	66.51%
CYP2C9 substrate	-	0.6049	60.49%
CYP2D6 substrate	-	0.8276	82.76%
CYP3A4 inhibition	-	0.9799	97.99%
CYP2C9 inhibition	-	0.9312	93.12%
CYP2C19 inhibition	-	0.9254	92.54%
CYP2D6 inhibition	-	0.9291	92.91%
CYP1A2 inhibition	-	0.8216	82.16%
CYP2C8 inhibition	-	0.9900	99.00%
CYP inhibitory promiscuity	-	0.9922	99.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6304	63.04%
Carcinogenicity (trinary)	Non-required	0.7059	70.59%
Eye corrosion	-	0.7850	78.50%
Eye irritation	-	0.5608	56.08%
Skin irritation	-	0.5731	57.31%
Skin corrosion	+	0.5278	52.78%
Ames mutagenesis	-	0.7328	73.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.7642	76.42%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8388	83.88%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	-	0.6721	67.21%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.5723	57.23%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	-	0.9402	94.02%
Androgen receptor binding	-	0.8867	88.67%
Thyroid receptor binding	-	0.8762	87.62%
Glucocorticoid receptor binding	-	0.9064	90.64%
Aromatase binding	-	0.9396	93.96%
PPAR gamma	-	0.8951	89.51%
Honey bee toxicity	-	0.9565	95.65%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8900	89.00%
Fish aquatic toxicity	-	0.7451	74.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.96%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.78%	96.09%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	90.77%	92.29%
CHEMBL2581	P07339	Cathepsin D	86.89%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.99%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.09%	99.17%

Plants that contains it

• Hordeum vulgare

Cross-Links

• PubChem: 10197842
• NPASS: NPC198196