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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H13NO2S
Molecular Weight 163.238
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLMETHIONINE

SMILES

C[S+](C)CC[C@H](N)C([O-])=O

InChI

InChIKey=YDBYJHTYSHBBAU-YFKPBYRVSA-N
InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/t5-/m0/s1

HIDE SMILES / InChI

Molecular Formula C6H13NO2S
Molecular Weight 163.238
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

METHYLMETHIONINE (S-Methionine methyl sulfonium, SMMS) chloride is a derivative of methionine metabolism in some plants. Methylmethionine has therapeutic effects on gastrointestinal ulceration potentially via its ability to promote dermal fibroblast migration and growth. The natural derivative Methylmethionine is biosynthesized from L-methionine which is first converted to S-adenosylmethionine. The subsequent conversion, involving replacement of the adenosyl group by a methyl group is catalyzed by the enzyme methionine S-methyltransferase. Methylmethionine is particularly abundant in plants, being more abundant than methionine. S-Methylmethionine is sometimes referred to as vitamin U, but it is not considered a true vitamin. The term was coined in 1950 by Garnett Cheney for uncharacterized anti-ulcerogenic factors in raw cabbage juice that may help speed healing of peptic ulcers.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
500 mg 4 times daily for 2 weeks
Route of Administration: Oral
In Vitro Use Guide
Evaluation of in vitro permeation and deposition of SMM (methylmethionine) through hairless mouse skin was carried out by using Keshary- Chien diffusion cells at 32°C, which have 1.77 cm2 of the surface area for diffusion. After sacrificing the hairless mice by cervical dislocation, the dorsal skin was cut to about 3 cm x 3 cm size and the subcutaneous fat was removed. Then, they were fixed between the donor and receptor cells, laying the stratum corneum toward the donor cells. The donor cells contained 2% (w/v) or 5% (w/v) SMM in the 50:50 (v/v) mixture (1.0 mL) of PG and double distilled water (DDW) with or without permeation enhancers, and were covered with parafilm to prevent evaporation. The receptor cells were filled with DDW (13.0 mL) and continuously stirred by magnetic bar. After applying SMM solution on the donor cells, 0.5 mL of the receptor solution was collected at 3, 6, 9, and 12 hr and added immediately with an equal volume of fresh media. SMM in the receptor solutions was analyzed using LC-MS/MS.
Substance Class Chemical
Record UNII
3485Y39925
Record Status Validated (UNII)
Record Version