Structure of S-Adenosyl-L-methionine
CAS No.: 29908-03-0
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Ademetionine is a naturally-occurring substance which is a methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. S-adenosylmethionine could form complex with SARS-CoV-2 nsp10-nsp16 2’-O-methyltransferase.
Synonyms: S-Adenosyl methionine; AdoMet; Gumbaral.
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Zhou, Jujun ; Deng, Youchao ; Iyamu, Iredia D. ; Horton, John R. ; Yu, Dan ; Hajian, Taraneh , et al.
Abstract: S-Adenosyl-L-methionine (SAM) analogs are adaptable tools for studying and therapeutically inhibiting SAM-dependent methyltransferases (MTases). Some MTases play significant roles in host-pathogen interactions, one of which is Clostridioides difficile-specific DNA adenine MTase (CamA). CamA is needed for efficient sporulation and alters persistence in the colon. To discover potent and selective CamA inhibitors, we explored modifications of the solvent-exposed edge of the SAM adenosine moiety. Starting from the two parental compounds (6e and 7), we designed an adenosine analog (11a) carrying a 3-phenylpropyl moiety at the adenine N6-amino group, and a 3-(cyclohexylmethyl guanidine)-Et moiety at the sulfur atom off the ribose ring. Compound 11a (IC50 = 0.15 μM) is 10x and 5x more potent against CamA than 6e and 7, resp. The structure of the CamA-DNA-inhibitor complex revealed that 11a adopts a U-shaped conformation, with the two branches folded toward each other, and the aliphatic and aromatic rings at the two ends interacting with one another. 11a occupies the entire hydrophobic surface (apparently unique to CamA) next to the adenosine binding site. Our work presents a hybrid knowledge-based and fragment-based approach to generating CamA inhibitors that would be chem. agents to examine the mechanism(s) of action and therapeutic potentials of CamA in C. difficile infection.
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Purchased from AmBeed: 2086772-26-9 ; 29908-03-0 ; 73-24-5 ; 83948-53-2 ; 39684-80-5 ; 58-61-7 ; 2004-06-0 ; 2038-57-5 ; 199915-38-3 ; 2040291-27-6 ; 3218-02-8 ; 1561178-17-3 ; 58944-73-3
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CAS No. : | 29908-03-0 |
Formula : | C15H22N6O5S |
M.W : | 398.44 |
SMILES Code : | O[C@@H]([C@H]([C@H](N1C=NC2=C1N=CN=C2N)O3)O)[C@H]3C[S+](CC[C@H](N)C([O-])=O)C |
Synonyms : |
S-Adenosyl methionine; AdoMet; Gumbaral.
|
MDL No. : | MFCD00871208 |
InChI Key : | MEFKEPWMEQBLKI-AIRLBKTGSA-N |
Pubchem ID : | 34755 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT03472820 | Lifestyle Die... More >>t Healthy Less << | Not Applicable | Recruiting | April 1, 2019 | United States, Oregon ... More >> NUNM Helfgott Research Institute Recruiting Portland, Oregon, United States, 97201 Contact: Trina Soileau Research Coordinator 503-552-1746 tsoileau@nunm.edu Contact: Emily Stack Research Coordinator 503-552-1777 estack@nunm.edu Principal Investigator: Ryan Bradley, ND, MPH Less << |
NCT02649777 | - | Completed | - | United States, Colorado ... More >> Children's Hospital Colorado Aurora, Colorado, United States, 80045 Less << | |
NCT03435250 | Advanced Solid Tumors ... More >> Lymphoma Less << | Phase 1 | Recruiting | October 2020 | United States, Connecticut ... More >> New Haven Recruiting New Haven, Connecticut, United States, 06519 United States, Massachusetts Boston Recruiting Boston, Massachusetts, United States, 02114 United States, New York New York Recruiting New York, New York, United States, 10065 United States, Tennessee Nashville Recruiting Nashville, Tennessee, United States, 37203 France Villejuif Cedex Not yet recruiting Villejuif Cedex, France, 94805 Spain Barcelona Not yet recruiting Barcelona, Spain, 08035 Less << |
NCT02812121 | Liver Failure | Phase 2 | Unknown | June 2018 | - |
NCT03535675 | Adenocarcinoma of the Prostate | Phase 3 | Recruiting | December 2021 | United States, District of Col... More >>umbia Sibley Memorial Hospital Recruiting Washington, District of Columbia, United States, 20016 Contact: Channing Paller, MD 202-660-6500 cpaller1@jhmi.edu United States, Maryland Johns Hopkins Hospital Recruiting Baltimore, Maryland, United States, 21205 Contact: Donna Dowling, RN 410-614-9526 ddowlin1@jhmi.edu Principal Investigator: Channing Paller, MD Less << |
NCT01964001 | Hepatocellular Carcinoma. | Phase 2 Phase 3 | Completed | - | Taiwan ... More >> Taichung Verterans General Hospital Taichung, Taiwan, 40705 Less << |
NCT00903695 | - | Terminated(Risk/benefit ratio ... More >>did not indicate further study would be useful, or fair to future subjects.) Less << | - | - | |
NCT02062892 | Kidney Transplantation | Phase 4 | Withdrawn(Patients meeting the... More >> inclusion/ exclusion criteria did not agree to participate. It became obvious that recruitment goals could not be met.) Less << | - | - |
NCT01320527 | Alzheimer's Disease ... More >> Mild Cognitive Impairment Less << | Phase 2 | Completed | - | United States, Florida ... More >> Naples Medical Center Naples, Florida, United States, 34102 United States, Maryland University of Maryland Baltimore, Maryland, United States, 21201 United States, Massachusetts Primary Care Cardiology Research Ayer, Massachusetts, United States, 01432 Rivercourt Residences Groton, Massachusetts, United States, 014590 Mary Immaculate Residential Lawrence, Massachusetts, United States, 01841 D'Youville Senior Care Lowell, Massachusetts, United States, 01854 United States, New Jersey Neurocognitive Institute Mt. Arlington, New Jersey, United States, 07856 United States, Utah Advanced Memory Dynamics Layton, Utah, United States, 84040 Less << |
NCT01844063 | Liver Failure | Phase 1 Phase 2 | Recruiting | January 2019 | China, Guangdong ... More >> Qi Zhang Recruiting Guangzhou, Guangdong, China, 510630 Principal Investigator: Qi Zhang, Doctor Less << |
NCT01749982 | - | Completed | - | - | |
NCT01360723 | - | Unknown | - | Taiwan ... More >> Department of Urology, China Medical University Hospital Recruiting Taichung, Taiwan, 404 Contact: Chao-Hsiang Chuang, PhD 886-4-22052121 ext 4439 urology8395@yahoo.com.tw Principal Investigator: Chi-Jung Chung, PhD Less << | |
NCT02264860 | HIV-1 Infection | Not Applicable | Recruiting | December 2018 | United States, Georgia ... More >> Ponce De Leon Center Recruiting Atlanta, Georgia, United States, 30308 Contact: Vincent Marconi, MD 404-616-0673 vcmarco@emory.edu Principal Investigator: David M Guidot, MD Less << |
NCT00956891 | - | Completed | - | China, Guangdong ... More >> The Third Affiliated Hospital Of Sun Yat-sen University Guangzhou, Guangdong, China, 510630 Less << | |
NCT01806870 | HIV | Not Applicable | Active, not recruiting | June 2019 | United States, Georgia ... More >> Grady Hospital- Ponce De Leon Clinic Atlanta, Georgia, United States, 30308 Atlanta VA Medical Center Decatur, Georgia, United States, 30033 Less << |
NCT02022046 | - | Completed | - | Taiwan ... More >> Kaohsiung Chang Gung Memorial Hospital Kaohsiung, Taiwan, 833 Less << | |
NCT02331745 | Liver Failure ... More >> Hepatitis B Alcoholic Liver Disease Less << | Phase 4 | Unknown | October 2016 | China ... More >> Beijing; 302 Military Hospital Recruiting Beijing, China, 100039 Contact: Jinbiao Ding, Dr. 86106693462 dingjb163@163.com Less << |
NCT01749982 | Arsenic Metabolites Measured i... More >>n Urine Less << | Phase 4 | Completed | - | Bangladesh ... More >> Columbia University Arsenic Research Project Dhaka, Bangladesh Less << |
NCT00070941 | - | Completed | - | - | |
NCT00903695 | Mild Cognitive Impairment | Phase 2 | Terminated(Risk/benefit ratio ... More >>did not indicate further study would be useful, or fair to future subjects.) Less << | - | United States, Oklahoma ... More >> Univ. of Okla. Health Sciences Center & VAMC OKC Oklahoma City, Oklahoma, United States, 73104 Veterans Affairs Medical Center Oklahoma City, Oklahoma, United States, 73104 Less << |
NCT02520206 | - | Unknown | August 2015 | - | |
NCT03266146 | Drug-induced Liver Injury,Chro... More >>nic Less << | Phase 1 Phase 2 | Recruiting | August 27, 2021 | China ... More >> Beijing 302 hospital Recruiting Beijing, China, 100039 Contact: Zhengsheng Zou, Dr. +8601066933424 zszou302@163.com Principal Investigator: Zhengsheng Zou, Dr. Less << |
NCT00513461 | Adult Primary Liver Cancer ... More >> Hepatitis C Infection Less << | Phase 2 | Completed | - | United States, Arizona ... More >> University of Arizona Health Sciences Center Tucson, Arizona, United States, 85724 United States, California Veterans Administration Long Beach Medical Center Long Beach, California, United States, 90822 Veterans Administration Los Angeles Healthcare System Los Angeles, California, United States, 90073 Chao Family Comprehensive Cancer Center Orange, California, United States, 92868 University of California At San Diego San Diego, California, United States, 92103 Less << |
NCT00070941 | Parkinson's Disease ... More >> Depression Less << | Phase 2 Phase 3 | Completed | - | United States, New York ... More >> New York University New York, New York, United States, 10003 Less << |
NCT02651350 | Drug-induced Liver Injury,Chro... More >>nic Less << | Phase 1 Phase 2 | Active, not recruiting | December 2019 | China, Beijing ... More >> Beijing 302 hospital,China Beijing, Beijing, China, 100039 Less << |
NCT01912196 | Major Depressive Disorder (MDD... More >>) Less << | Phase 2 | Completed | - | - |
NCT01754714 | Non Alcoholic Fatty Liver Dise... More >>ase Less << | Phase 3 | Completed | - | France ... More >> Site Reference ID 93914 Amiens, France, 80054 Site Reference ID 93895 Angers, France, 49933 Site Reference ID 93894 Bobigny, France, 93009 Site Reference ID 93913 Montpellier, France, 34295 Site Reference ID 93916 Nice, France, 06202 Site Reference ID 93915 Paris, France, 75012 Site Reference ID 93893 Paris, France, 75651 Site Reference ID 93896 Pessac, France, 33604 Germany Site Reference ID 93953 Bonn, Germany, 53127 Site Reference ID 93954 Frankfurt, Germany, 60594 Site Reference ID 93935 Freiburg, Germany, 79106 Site Reference ID 93955 Halle, Germany, 06120 Site Reference ID 93917 Hannover, Germany, 30625 Site Reference ID 93933 Homburg, Germany, 66424 Site Reference ID 94015 Leipzig, Germany, 04103 Site Reference ID 93918 Mainz, Germany, 55131 Site Reference ID 94014 Ulm, Germany, 89081 Poland Site reference ID/Investigator # 109455 Bydgoszcz, Poland, 85-030 Site Reference ID 93958 Chorzow, Poland, 41-500 Site Reference ID 93973 Krakow, Poland, 31-531 Site Reference ID 93956 Lodz, Poland, 91-347 Site Reference ID 93957 Myslowice, Poland, 41-400 Site Reference ID 93974 Warsaw, Poland, 02-507 Site Reference ID 93975 Wroclaw, Poland, 50-220 Russian Federation Site reference ID ORG-000905 Krasnoyarsk, Russian Federation, 660022 Site reference ID ORG-000906 Moscow, Russian Federation, 119435 Site reference ID ORG-000900 Nizhniy Novgorod, Russian Federation, 603126 Site reference ID ORG-000907 Novosibirsk, Russian Federation, 630084 Site reference ID ORG-000903 Omsk, Russian Federation, 644043 Site reference ID ORG-000920 Rostov-on-Don, Russian Federation, 344022 Site reference ID ORG-000904 Samara, Russian Federation, 443011 Site reference ID ORG-000901 Stavropol, Russian Federation, 355017 Less << |
NCT00513461 | - | Completed | - | - | |
NCT00093847 | - | Completed | - | - | |
NCT00851981 | Alcoholic Hepatitis | Phase 2 | Completed | - | United States, California ... More >> Loma Linda University Loma Linda, California, United States, 92354 Less << |
NCT00284011 | Heart Disease | Not Applicable | Completed | - | United States, Minnesota ... More >> Mayo Clinic Rochester, Minnesota, United States, 55905 Less << |
NCT01754714 | - | Completed | - | - | |
NCT00762268 | Bipolar Disorder ... More >> Depression Bipolar Depression Less << | Not Applicable | Completed | - | United States, Massachusetts ... More >> McLean Hospital Belmont, Massachusetts, United States, 02478 Less << |
NCT00762268 | - | Completed | - | - | |
NCT00125281 | Liver Cirrhosis, Biliary | Phase 2 | Terminated | - | United States, Maryland ... More >> National Institutes of Health Clinical Center, 9000 Rockville Pike Bethesda, Maryland, United States, 20892 Less << |
NCT00093847 | Depression | Phase 2 | Completed | - | United States, Massachusetts ... More >> Massachusetts General Hospital Boston, Massachusetts, United States, 02114 Less << |
NCT01140646 | Healthy, no Evidence of Diseas... More >>e Hot Flashes Less << | Phase 2 | Completed | - | United States, Minnesota ... More >> Mayo Clinic Rochester, Minnesota, United States, 55905 Less << |
NCT02024295 | Hepatitis, Alcoholic | Phase 4 | Unknown | December 2015 | China, Beijing ... More >> Beijing Ditan Hospital Recruiting Beijing, Beijing, China, 100015 Contact: Jun Cheng 8610-84322566 jun.cheng.ditan@gmail.com Jun Cheng Recruiting Beijing, Beijing, China, 100015 Contact: Jun Cheng Less << |
NCT00573313 | - | Completed | - | - | |
NCT01899521 | Alcoholism | Not Applicable | Completed | - | United States, Georgia ... More >> Atlanta VA Medical and Rehab Center, Decatur, GA Decatur, Georgia, United States, 30033 Less << |
NCT00573313 | Liver Disease, Alcoholic | Phase 3 | Completed | - | United States, California ... More >> University of California, Davis Medical Center Sacramento, California, United States, 95817 Less << |
NCT03178929 | Primary Liver Cancer | Not Applicable | Not yet recruiting | August 31, 2020 | - |
NCT00722124 | Tobacco Dependence | Phase 2 Phase 3 | Completed | - | United States, Minnesota ... More >> Mayo Clinic Rochester, Minnesota, United States, 55905 United States, Wisconsin Franciscan Skemp HealthCare La Crosse, Wisconsin, United States, 54601 Less << |
NCT01140646 | - | Completed | - | - | |
NCT00722124 | - | Completed | - | - | |
NCT00101452 | - | Completed | - | - | |
NCT00101452 | Depression | Not Applicable | Completed | - | United States, Massachusetts ... More >> Massachusetts General Hospital Boston, Massachusetts, United States, 02114 United States, Rhode Island Butler Hospital Providence, Rhode Island, United States, 02906 Less << |
NCT00475176 | Chronic Hepatitis C | Phase 2 | Completed | - | United States, Maryland ... More >> National Institutes of Health Clinical Center, 9000 Rockville Pike Bethesda, Maryland, United States, 20892 Less << |
NCT00310336 | Hepatitis C | Phase 2 Phase 3 | Completed | - | Switzerland ... More >> University Hospital Basel Basel, BS, Switzerland, 4031 Less << |
NCT00475176 | - | Completed | - | - | |
NCT00694564 | Abdominal Pain | Not Applicable | Completed | - | United States, California ... More >> University of California, San Diego San Diego, California, United States, 92103 Less << |
NCT00694564 | - | Completed | - | - | |
NCT02231333 | Non-alcoholic Steatohepatitis | Not Applicable | Unknown | June 2016 | India ... More >> Institute of Liver & Biliary Sciences Recruiting New Delhi, Delhi, India, 110070 Contact: Dr Devraj K, MD 011-46300000 drdevurgowda@gmail.com Less << |
NCT00473200 | Hyperhomocysteinemia | Phase 1 | Completed | - | United States, Texas ... More >> Baylor University Medical Center Dallas, Texas, United States, 75204 Less << |
NCT01998620 | Hepatitis B C... More >>holestasis Less << | Phase 4 | Unknown | May 2015 | China, Shanghai ... More >> Public Health Clinical Center Affiliated to Fudan University Recruiting Shanghai, Shanghai, China, 200000 Contact: Liang Chen, Doctor 00862137990333 chenlian@shaphl.org Less << |
NCT00528710 | Fibromyalgia Syndrome | Phase 2 | Completed | - | Australia, Victoria ... More >> Deakin University Burwood, Victoria, Australia, 3125 Less << |
NCT02200029 | Intrahepatic Cholestasis Assoc... More >>iated With Alcoholic Liver Disease Less << | Phase 3 | Completed | - | Russian Federation ... More >> Research facility ORG-000962 Moscow, Russian Federation, 107014 Research facility ORG-000957 Moscow, Russian Federation, 117292 Research facility ORG-000961 Moscow, Russian Federation, 119435 Research facility ID ORG-000960 Moscow, Russian Federation, 119992 Research facility ID ORG-000726 Moscow, Russian Federation, 125284 Research facility ORG-000967 St. Petersburg, Russian Federation, 117630 Research facility ORG-000966 St. Petersburg, Russian Federation, 191015 Research facility ORG-000968 St. Petersburg, Russian Federation, 195257 Research facility ORG-000965 St. Petersburg, Russian Federation, 197022 Research facility ORG-000970 St. Petersburg, Russian Federation, 198216 Research facility ORG-000958 Troitsk, Russian Federation, 142190 Research facility ORG-000969 Yaroslavl, Russian Federation, 150003 Less << |
NCT00108589 | Hepatitis | Phase 3 | Completed | - | United States, Kentucky ... More >> VA Medical Center Louisville, Kentucky, United States, 40206 Less << |
NCT02557360 | Primary Biliary Cirrhosis | Phase 4 | Completed | - | Poland ... More >> Wunsch Szczecin, Poland Milkiewicz Warsaw, Poland Less << |
NCT02586285 | Hepatocellular Carcinoma | Phase 1 | Unknown | December 2017 | China, Shanghai ... More >> Eastern hepatobilliary surgery hospital Recruiting Shanghai, Shanghai, China, 200438 Contact: Shen Feng, MD 0086-021-25070805 shenfengdfgd@yahoo.com.cn Contact: Yong Xia, Doctor 86-021-81875495 Principal Investigator: Shen Feng, MD Less << |
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1mg | 5mg | 10mg |
1 mM 5 mM 10 mM |
2.51mL 0.50mL 0.25mL |
12.55mL 2.51mL 1.25mL |
25.10mL 5.02mL 2.51mL |