S-Adenosyl-L-methionine - Moligand™, 10mM in DMSO , CAS No.29908-03-0

CAS: 29908-03-0 Cat. No.: S580508 Molecular Weight: 398.44 EC Number: 249-946-8 PubChem CID: 34755

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

S-adenosyl-L-methionine|S-adenosylmethionine|Ademetionine|29908-03-0|AdoMet|SAM-e|SAMe|adenosylmethionine|Donamet|Methioninyladenylate|Active methionine|L-S-Adenosylmethionine|S Amet|Transmetil|Ademetionine, (S)-|CCRIS 7130|S-adenosyl-L-methioninate|L-Met

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

S-Adenosyl-L-methionine is an intermediate metabolite of methionine,for treatment of primary biliary cirrhosis and major depressive disorder.

Specifications

Synonyms

S-adenosyl-L-methionine | S-adenosylmethionine | Ademetionine | 29908-03-0 | AdoMet | SAM-e | SAMe | adenosylmethionine | Donamet | Methioninyladenylate | Active methionine | L-S-Adenosylmethionine | S Amet | Transmetil | Ademetionine, (S)- | CCRIS 7130 | S-adenosyl-L-methioninate | L-Met

Specifications & Purity

Moligand™, 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: C[S+](CCC(C(=O)[O-])N)CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• IUPAC Name: (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-methylsulfonio]butanoate
• InChIKey: MEFKEPWMEQBLKI-AIRLBKTGSA-N
• 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
• Isomeric SMILES: C[S+](CC[C@@H](C(=O)[O-])N)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• Alternate CAS: 97540-22-2
• PubChem CID: 34755
• Molecular Weight: 398.44

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class 5'-deoxyribonucleosides
      • Subclass 5'-deoxy-5'-thionucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: 5'-deoxyribonucleosides
• Subclass: 5'-deoxy-5'-thionucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: 5'-deoxy-5'-thionucleosides
• Alternative Parents: Methionine and derivatives Glycosylamines Pentoses 6-aminopurines L-alpha-amino acids Thia fatty acids Aminopyrimidines and derivatives Hydroxy fatty acids N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols 1,2-diols Amino acids Carboxylic acid salts Oxacyclic compounds Azacyclic compounds Carboxylic acids Monocarboxylic acids and derivatives Organopnictogen compounds Organic salts Carbonyl compounds Organosulfur compounds Organic oxides Organic zwitterions Hydrocarbon derivatives Monoalkylamines
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: Coenzymes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 398.400 g/mol
• XLogP3: -2.800
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 398.137 Da
• Monoisotopic Mass: 398.137 Da
• Topological Polar Surface Area: 186.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 527.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Liao Zhenkun, Liu Xiaojuan, Zheng Juan, Zhao Chenning, Wang Dengliang, Xu Yang, Sun Chongde.  (2023)  A multifunctional true caffeoyl coenzyme A O-methyltransferase enzyme participates in the biosynthesis of polymethoxylated flavones in citrus.  PLANT PHYSIOLOGY,      [PMID:37086474] [10.1093/plphys/kiad249]

2. Guorong Cheng, Zhiqiang Liu, Zhong Zheng, Fengrui Song, Xiaoyu Zhuang, Shu Liu.  (2022)  Cell Metabolomics Reveals the Potential Mechanism of Aloe Emodin and Emodin Inhibiting Breast Cancer Metastasis.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  23  (22): (13738).  [PMID:36430215] [10.3390/ijms232213738]

3. Zijin Xu, Susu Lin, Zheren Tong, Suhong Chen, Yifeng Cao, Qiaoqiao Li, Yuli Jiang, Weijie Cai, Yingpeng Tong, Bathaie S. Zahra, Ping Wang.  (2021)  Crocetin ameliorates non-alcoholic fatty liver disease by modulating mitochondrial dysfunction in L02 cells and zebrafish model.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:34848360] [10.1016/j.jep.2021.114873]

4. Liu Xiaojuan, Zhao Chenning, Gong Qin, Wang Yue, Cao Jinping, Li Xian, Grierson Donald, Sun Chongde.  (2020)  Characterization of a caffeoyl-CoA O-methyltransferase-like enzyme involved in biosynthesis of polymethoxylated flavones in Citrus reticulata.  JOURNAL OF EXPERIMENTAL BOTANY,  71  (10): (3066-3079).  [PMID:32182355] [10.1093/jxb/eraa083]

5. Xiaojuan Liu, Yue Wang, Yezhi Chen, Shuting Xu, Qin Gong, Chenning Zhao, Jinping Cao, Chongde Sun.  (2020)  Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the In Vitro Cytotoxicity of Its Methylated Products.  MOLECULES,  25  (4): (858).  [PMID:32075249] [10.3390/molecules25040858]

6. Wei Chen, Chaoman Ang, Doudou Lou, Yongxin Ji, Ling Huang, Yefei Zhu, Zhirui Guo, Ning Gu, Yu Zhang.  (2018)  Fast immunofluorescence lateral flow test strip approach for detection of homocysteine.  Micro & Nano Letters,  13  (12): (1719-1723).  [PMID:] [10.1049/mnl.2018.5040]

7. Liu Hui-Jun, Jing Peng-Fei, Liu Xiu-Yun, Du Ke-Jie, Sun Yun-Kai.  (2016)  Synthesis of β-cyclodextrin functionalized silica gel and its application for adsorption of uranium(VI).  JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY,  310  (1): (263-270).  [PMID:] [10.1007/s10967-016-4792-7]

8. Lili Wang, Jing Wu, Qin Wang, Chonghui He, Lei Zhou, Jing Wang, Qiaosheng Pu.  (2012)  Rapid and Sensitive Determination of Sulfonamide Residues in Milk and Chicken Muscle by Microfluidic Chip Electrophoresis.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:22277081] [10.1021/jf2036577]

9. Shulong Wang, Yanni Luo, Jianniao Tian, Fanggui Ye, Zhihui Luo, Shulin Zhao.  (2024)  A mart-responsive photoacoustic sensor based on metal-organic framework as bioreactor for in situ visualization of hydrogen sulfide and tracking of drug-induced liver injury by NIR-II imaging.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2024.135561]

10. Meng-Qi Wang, Ming-Xin Sun, Han-Guang Li, Ze-Hua Wu, Jian-Zhong Xu.  (2024)  Combining Protein Engineering and Pathway Engineering to Achieve Green Biosynthesis of l-Hypaphorine in Escherichia coli from Glucose.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.4c00640]

11. Yamin Liu, Xunjiang Wang, Jiaojiao Wei, Kangning Fu, Yilin Chen, Linnan Li, Zhengtao Wang, Li Yang.  (2024)  Comprehensive Profiling of Amino Acids and Derivatives in Biological Samples: A Robust UHPLC-MS/MS Method for Investigating Acute Lung Injury.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:38537486] [10.1016/j.chroma.2024.464816]

12. Moli Sang, Qingyu Yang, Jiawei Guo, Peiyuan Feng, Wencheng Ma, Wei Zhang.  (2024)  Functional investigation of the SAM-dependent methyltransferase RdmB in anthracycline biosynthesis.  Synthetic and Systems Biotechnology,      [PMID:39308748] [10.1016/j.synbio.2024.09.002]

13. Yongli Zhang, Zhao Zhou, Jun Wu, Yiyang Shi, Xinxiao Sun, Jia Wang, Xiaolin Shen, Qipeng Yuan.  (2025)  Construction and application of an efficient methylation platform in Escherichia coli based on SAM regeneration.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.162642]

14. Wenhui Zhang, Min Zhao, Leqiang Wang, Jiaqi Wang, Xiaoguang Ge, Junzhi Liu, Bin Chen, Shi Gao, Jingbin Lu.  (2025)  Dual NIR-II fluorescence and ratiometric photoacoustic imaging-guided metal-phenolic nanosheets for H2S-activatable synergistic therapy.  iScience,      [PMID:40352725] [10.1016/j.isci.2025.112425]

15. Xiran Xiong, Jun Song, Shihan Li, Lu Jin, Qi He, Baohui Zhang, Yan Cao, Shanyong Yi, Yanfang Yang, Xiang Li, Juan Li, Wei Huang.  (2025)  Structure-Guided Engineering of a Promiscuous O-Methyltransferase for a SAM Regeneration Biocatalysis Platform of Methylated Pharmaceuticals.  Advanced Science,      [PMID:41417579] [10.1002/advs.202517794]

16. Moli Sang, Qingyu Yang, Jiawei Guo, Peiyuan Feng, Yu Gao, Wencheng Ma, Shengying Li, Mikko Metsä-Ketelä, Wei Zhang.  (2026)  Functional Plasticity of Methyltransferases in Anthracycline Biosynthesis: A Single Residue Reversal between Decarboxylation and Hydroxylation.  ACS Catalysis,      [PMID:] [10.1021/acscatal.5c07819]