S-Adenosylhomocysteine | CAS#979-92-0 | amino acid derivative

MedKoo Cat#: 597349 | Name: S-Adenosylhomocysteine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

S-Adenosylhomocysteine (SAH), also known as S-(5’-Adenosyl)-L-homocysteine, is an amino acid derivative used in several metabolic pathways in most organisms. It is an intermediate in the synthesis of cysteine and adenosine.

Chemical Structure

S-Adenosylhomocysteine

CAS#979-92-0

Theoretical Analysis

MedKoo Cat#: 597349

Name: S-Adenosylhomocysteine

CAS#: 979-92-0

Chemical Formula: C14H20N6O5S

Exact Mass: 384.1216

Molecular Weight: 384.41

Elemental Analysis: C, 43.74; H, 5.24; N, 21.86; O, 20.81; S, 8.34

Price and Availability

Size	Price	Availability
5mg	USD 100.00	2 Weeks
10mg	USD 350.00	2 weeks
25mg	USD 600.00	2 Weeks
50mg	USD 850.00	2 Weeks

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Synonym

S-Adenosyl-L-homocysteine; S-Adenosylhomocysteine; S Adenosylhomocysteine; S-(5′-Adenosyl)-L-homocysteine;

IUPAC/Chemical Name

(5S)-2-amino-5-((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-mercaptopentanoic acid

InChi Key

QLARQQFYXNHLNY-QMEGSSTCSA-N

InChi Code

InChI=1S/C14H20N6O5S/c15-5(14(23)24)1-2-6(26)10-8(21)9(22)13(25-10)20-4-19-7-11(16)17-3-18-12(7)20/h3-6,8-10,13,21-22,26H,1-2,15H2,(H,23,24)(H2,16,17,18)/t5?,6-,8-,9+,10+,13+/m0/s1

SMILES Code

S[C@@H](CCC(N)C(O)=O)[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N=CN=C32)N)O1)O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO and 1M HCl

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SAH is an amino acid derivative and an intermediate, by-product, or modulator of several metabolic pathways, including the activated methyl cycle and cysteine biosynthesis. It is also a product of S-adenosyl-methionine (SAM)-dependent methylation of biological molecules, including DNA, RNA, and histones and other proteins.

In vitro activity:

In this study, excess SAH increased the expression of adhesion molecules and cytokines in human coronary artery endothelial cells. SAH accumulation triggered the activation of NFkB pathways while decreasing the levels of the epigenetic regulator EZH2 and histone 3 lysine 27 trimethylation. Reference: Biochim Biophys Acta. 2016 Jan;1862(1):82-92. https://pubmed.ncbi.nlm.nih.gov/26506125/

In vivo activity:

In this study, SAH was found to be a valuable predictor of disease progression and survival in critically ill patients with inflammatory and septic conditions. SAH levels significantly contributed to predicting the severity of the disease and the likelihood of death. The ratio of SAM to SAH was notably decreased in patients with septic organ dysfunction and non-survivors. Reference: Int J Mol Sci. 2023 Aug 9;24(16):12600. https://pubmed.ncbi.nlm.nih.gov/37628779/

	Solvent	mg/mL	mM
Solubility
	DMSO	125.0	325.17
	1M HCl	20.0	52.03

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 384.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Barroso M, Kao D, Blom HJ, Tavares de Almeida I, Castro R, Loscalzo J, Handy DE. S-adenosylhomocysteine induces inflammation through NFkB: A possible role for EZH2 in endothelial cell activation. Biochim Biophys Acta. 2016 Jan;1862(1):82-92. doi: 10.1016/j.bbadis.2015.10.019. Epub 2015 Oct 24. PMID: 26506125; PMCID: PMC4674364. 2. Ngo S, Li X, O'Neill R, Bhoothpur C, Gluckman P, Sheppard A. Elevated S-adenosylhomocysteine alters adipocyte functionality with corresponding changes in gene expression and associated epigenetic marks. Diabetes. 2014 Jul;63(7):2273-83. doi: 10.2337/db13-1640. Epub 2014 Feb 26. PMID: 24574043. 3. Centner FS, Schoettler JJ, Brohm K, Mindt S, Jäger E, Hahn B, Fuderer T, Lindner HA, Schneider-Lindner V, Krebs J, Neumaier M, Thiel M. S-Adenosylhomocysteine Is a Useful Metabolic Factor in the Early Prediction of Septic Disease Progression and Death in Critically Ill Patients: A Prospective Cohort Study. Int J Mol Sci. 2023 Aug 9;24(16):12600. doi: 10.3390/ijms241612600. PMID: 37628779; PMCID: PMC10454796. 4. Xiao Y, Huang W, Zhang J, Peng C, Xia M, Ling W. Increased plasma S-adenosylhomocysteine-accelerated atherosclerosis is associated with epigenetic regulation of endoplasmic reticulum stress in apoE-/- mice. Arterioscler Thromb Vasc Biol. 2015 Jan;35(1):60-70. doi: 10.1161/ATVBAHA.114.303817. Epub 2014 Oct 30. PMID: 25359864.

In vitro protocol:

In vivo protocol:

1. Centner FS, Schoettler JJ, Brohm K, Mindt S, Jäger E, Hahn B, Fuderer T, Lindner HA, Schneider-Lindner V, Krebs J, Neumaier M, Thiel M. S-Adenosylhomocysteine Is a Useful Metabolic Factor in the Early Prediction of Septic Disease Progression and Death in Critically Ill Patients: A Prospective Cohort Study. Int J Mol Sci. 2023 Aug 9;24(16):12600. doi: 10.3390/ijms241612600. PMID: 37628779; PMCID: PMC10454796. 2. Xiao Y, Huang W, Zhang J, Peng C, Xia M, Ling W. Increased plasma S-adenosylhomocysteine-accelerated atherosclerosis is associated with epigenetic regulation of endoplasmic reticulum stress in apoE-/- mice. Arterioscler Thromb Vasc Biol. 2015 Jan;35(1):60-70. doi: 10.1161/ATVBAHA.114.303817. Epub 2014 Oct 30. PMID: 25359864.

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NNMT activation can contribute to the development of fatty liver disease by modulating the NAD (+) metabolism. Sci Rep. 2018 Jun 5;8(1):8637. doi: 10.1038/s41598-018-26882-8. PubMed PMID: 29872122; PubMed Central PMCID: PMC5988709. 4: Fu Y, Wang W, Li X, Liu Y, Niu Y, Zhang B, Nie J, Pan B, Wang R, Yang J. LncRNA H19 interacts with S-adenosylhomocysteine hydrolase to regulate LINE-1 Methylation in human lung-derived cells exposed to Benzo[a]pyrene. Chemosphere. 2018 Sep;207:84-90. doi: 10.1016/j.chemosphere.2018.05.048. Epub 2018 May 9. PubMed PMID: 29772428. 5: Ponnaluri VKC, Estève PO, Ruse CI, Pradhan S. S-adenosylhomocysteine Hydrolase Participates in DNA Methylation Inheritance. J Mol Biol. 2018 Jul 6;430(14):2051-2065. doi: 10.1016/j.jmb.2018.05.014. Epub 2018 May 28. PubMed PMID: 29758262. 6: Fick RJ, Clay MC, Vander Lee L, Scheiner S, Al-Hashimi H, Trievel RC. Water-Mediated Carbon-Oxygen Hydrogen Bonding Facilitates S-Adenosylmethionine Recognition in the Reactivation Domain of Cobalamin-Dependent Methionine Synthase. Biochemistry. 2018 May 21. doi: 10.1021/acs.biochem.8b00375. [Epub ahead of print] PubMed PMID: 29733595. 7: Bai Z, Qi T, Liu Y, Wu Z, Ma L, Liu W, Cao Y, Bao Y, Fu C. Alteration of S-adenosylhomocysteine levels affects lignin biosynthesis in switchgrass. Plant Biotechnol J. 2018 Apr 28. doi: 10.1111/pbi.12935. [Epub ahead of print] PubMed PMID: 29704888. 8: Fan X, Rao J, Zhang Z, Li D, Cui W, Zhang J, Wang H, Tou F, Zheng Z, Shen Q. Macranthoidin B Modulates Key Metabolic Pathways to Enhance ROS Generation and Induce Cytotoxicity and Apoptosis in Colorectal Cancer. Cell Physiol Biochem. 2018;46(4):1317-1330. doi: 10.1159/000489147. Epub 2018 Apr 18. PubMed PMID: 29689551. 9: Cueto R, Zhang L, Shan HM, Huang X, Li X, Li YF, Lopez J, Yang WY, Lavallee M, Yu C, Ji Y, Yang X, Wang H. Identification of homocysteine-suppressive mitochondrial ETC complex genes and tissue expression profile - Novel hypothesis establishment. Redox Biol. 2018 Jul;17:70-88. doi: 10.1016/j.redox.2018.03.015. Epub 2018 Apr 4. PubMed PMID: 29679893; PubMed Central PMCID: PMC6006524. 10: Awwad HM, Ohlmann CH, Stoeckle M, Geisel J, Obeid R. Serum concentrations of folate vitamers in patients with a newly diagnosed prostate cancer or hyperplasia. Clin Biochem. 2018 Jun;56:41-46. doi: 10.1016/j.clinbiochem.2018.04.011. Epub 2018 Apr 16. PubMed PMID: 29673813. 11: Christensen KE, Bahous RH, Hou W, Deng L, Malysheva OV, Arning E, Bottiglieri T, Caudill MA, Jerome-Majewska LA, Rozen R. Low Dietary Folate Interacts with MTHFD1 Synthetase Deficiency in Mice, a Model for the R653Q Variant, to Increase Incidence of Developmental Delays and Defects. J Nutr. 2018 Apr 1;148(4):501-509. doi: 10.1093/jn/nxy013. PubMed PMID: 29659962. 12: Hu X, Wang Y, Gao L, Jiang W, Lin W, Niu C, Yuan K, Ma R, Huang Z. The Impairment of Methyl Metabolism From luxS Mutation of Streptococcus mutans. Front Microbiol. 2018 Mar 12;9:404. doi: 10.3389/fmicb.2018.00404. eCollection 2018. PubMed PMID: 29657574; PubMed Central PMCID: PMC5890193. 13: McKenna J 3rd, Kapfhamer D, Kinchen JM, Wasek B, Dunworth M, Murray-Stewart T, Bottiglieri T, Casero RA Jr, Gambello MJ. Metabolomic studies identify changes in transmethylation and polyamine metabolism in a brain-specific mouse model of tuberous sclerosis complex. Hum Mol Genet. 2018 Jun 15;27(12):2113-2124. doi: 10.1093/hmg/ddy118. PubMed PMID: 29635516; PubMed Central PMCID: PMC5985733. 14: Samiec M, Skrzyszowska M. Intrinsic and extrinsic molecular determinants or modulators for epigenetic remodeling and reprogramming of somatic cell-derived genome in mammalian nuclear-transferred oocytes and resultant embryos. Pol J Vet Sci. 2018 Mar;21(1):217-227. doi: 10.24425/119040. PubMed PMID: 29624006. 15: Ji X, Mandalapu D, Cheng J, Ding W, Zhang Q. Expanding the Chemistry of the Class C Radical SAM Methyltransferase NosN by Using an Allyl Analogue of SAM. Angew Chem Int Ed Engl. 2018 May 28;57(22):6601-6604. doi: 10.1002/anie.201712224. Epub 2018 Apr 26. PubMed PMID: 29603551. 16: Ruszkowska A, Ruszkowski M, Dauter Z, Brown JA. Structural insights into the RNA methyltransferase domain of METTL16. Sci Rep. 2018 Mar 28;8(1):5311. doi: 10.1038/s41598-018-23608-8. PubMed PMID: 29593291; PubMed Central PMCID: PMC5871880. 17: Esse R, Teerlink T, Koolwijk P, Tavares de Almeida I, Blom HJ, Castro R. Folinic Acid Increases Protein Arginine Methylation in Human Endothelial Cells. Nutrients. 2018 Mar 24;10(4). pii: E404. doi: 10.3390/nu10040404. PubMed PMID: 29587354; PubMed Central PMCID: PMC5946189. 18: Won SB, Kwon YH. Maternal Consumption of Low-Isoflavone Soy Protein Isolate Confers the Increased Predisposition to Alcoholic Liver Injury in Adult Rat Offspring. Nutrients. 2018 Mar 10;10(3). pii: E332. doi: 10.3390/nu10030332. 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