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17176-17-9 molecular structure
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[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium 4-methylbenzene-1-sulfonate

ChemBase ID: 133635
Molecular Formular: C22H30N6O8S2
Molecular Mass: 570.639
Monoisotopic Mass: 570.15665395
SMILES and InChIs

SMILES:
Cc1ccc(cc1)S(=O)(=O)[O-].C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O
Canonical SMILES:
C[S+](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)N.Cc1ccc(cc1)S(=O)(=O)[O-]
InChI:
InChI=1S/C15H22N6O5S.C7H8O3S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21;1-6-2-4-7(5-3-6)11(8,9)10/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);2-5H,1H3,(H,8,9,10)/t7-,8+,10+,11+,14+,27?;/m0./s1
InChIKey:
VHPOFDUCFKOUHV-XKGORWRGSA-N

Cite this record

CBID:133635 http://www.chembase.cn/molecule-133635.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium 4-methylbenzene-1-sulfonate
IUPAC Traditional name
SAMe tosylate
Synonyms
AdoMet
SAM p-toluenesulfonate salt
S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt
5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-Adenosine tosylate
CAS Number
17176-17-9
52248-03-0
MDL Number
MFCD00063498
PubChem SID
162227912
24890653
PubChem CID
10153079

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 10153079 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Rotatable Bonds Lipinski's Rule of Five false 
Acid pKa 1.7050833  H Acceptors 10 
H Donor LogD (pH = 5.5) -5.2821803 
LogD (pH = 7.4) -5.3258553  Log P -5.3224516 
Molar Refractivity 96.2349 cm3 Polarizability 38.568764 Å3
Polar Surface Area 182.63 Å2

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble100 mg/mL expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥80% (HPLC) expand Show data source
≥80% (spectrophotometric assay) expand Show data source
95% expand Show data source
Compostion
p-Toluenesulfonate content, 1.6-4.4 mol/mol expand Show data source
Biological Source
from yeast (L-methionine enriched) expand Show data source
Shipped in
dry ice expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - A2408 external link
Biochem/physiol Actions
S-(5′-Adenosyl)-L-methionine (SAM) is anti-apoptotic in normal hepatocytes and normal colon epithelial cells but pro-apoptotic in liver human hepatocellular carcinoma (HCC), HepG2 cells and colon cancer cells.
Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. It is also involved in regulating liver function, growth, and response to injury.
Caution
This material is unstable at room temperature.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

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