ChemFOnt: Showing chemical card for S-adenosyl-L-methioninate (CFc000043121)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:46:01 UTC

Chemfont ID

CFc000043121

Molecule Identification

Common Name

S-adenosyl-L-methioninate

Definition

S-adenosyl-L-methioninate, also known as SAM or AdoMet, is classified as a member of the 5'-deoxy-5'-thionucleosides. 5'-deoxy-5'-thionucleosides are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. S-adenosyl-L-methioninate is considered to be slightly soluble (in water) and acidic

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
AdoMet	ChEBI
S-Adenosylmethionine	ChEBI
SAM	ChEBI
ADEMETIONINE	ChEMBL
S-Adenosyl-L-methioninic acid	Generator
Gumbaral	HMDB, MeSH
S Adenosyl L methionine	HMDB, MeSH
S Adenosylmethionine	HMDB, MeSH
S Adenosylmethionine sulfate tosylate	HMDB, MeSH
S Amet	HMDB, MeSH
S-Adenosyl-L-methionine	HMDB, MeSH
S-Adenosylmethionine sulfate tosylate	HMDB, MeSH
SAM-e	HMDB, MeSH
Samyr	HMDB, MeSH

Chemical Formula

C₁₅H₂₂N₆O₅S

Average Molecular Weight

398.44

Monoisotopic Molecular Weight

398.137239006

IUPAC Name

(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate

Traditional Name

S-adenosyl methionine

CAS Registry Number

29908-03-0

SMILES

C[S+](CC[C@H](N)C([O-])=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C15H22N6O5S/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/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/t7-,8+,10+,11+,14+,27?/m0/s1

InChI Key

MEFKEPWMEQBLKI-AIRLBKTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

5'-deoxyribonucleosides

Sub Class

5'-deoxy-5'-thionucleosides

Direct Parent

5'-deoxy-5'-thionucleosides

Alternative Parents

Substituents

5'-deoxy-5'-thionucleoside
Methionine or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Alpha-amino acid
Alpha-amino acid or derivatives
Pentose monosaccharide
L-alpha-amino acid
Purine
Imidazopyrimidine
Aminopyrimidine
Thia fatty acid
Hydroxy fatty acid
Imidolactam
Monosaccharide
N-substituted imidazole
Fatty acyl
Pyrimidine
Heteroaromatic compound
Azole
Tetrahydrofuran
Imidazole
1,2-diol
Amino acid or derivatives
Amino acid
Carboxylic acid salt
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organosulfur compound
Organic oxygen compound
Primary amine
Carbonyl group
Alcohol
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Organic salt
Primary aliphatic amine
Amine
Organic zwitterion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonium betaine (CHEBI:67040 )
Coenzymes (C00019 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062709)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.62 g/L	ALOGPS
logP	0.05	ALOGPS
logP	-5.3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.7	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	185.46 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.07 m³·mol⁻¹	ChemAxon
Polarizability	39.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon