(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid

Details

• Internal ID: 576d6591-0636-4eea-91c7-459f902e5516
• Taxonomy: Nucleosides, nucleotides, and analogues > 5-deoxyribonucleosides > 5-deoxy-5-thionucleosides
• IUPAC Name: 2-amino-4-[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid
• SMILES (Canonical): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CSCCC(C(=O)O)N)O)O)N
• SMILES (Isomeric): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CSCCC(C(=O)O)N)O)O)N
• InChI: InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)
• InChI Key: ZJUKTBDSGOFHSH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₀N₆O₅S
• Molecular Weight: 384.41 g/mol
• Exact Mass: 384.12158893 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: -3.50

Synonyms

• S-(5''-Adenosyl)-D-homocysteine
• (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid
• 53276-26-9
• 58976-18-4
• SAH (S-Adenosylhomocysteine)
• MFCD00037388
• SCHEMBL12436336
• DTXSID90862497
• CHEBI:181457
• BCP31730
• 5-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE
• SY357809
• FT-0661430
• 2-amino-4-[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulanyl]butanoic acid
• (S)-2-Amino-4-[[[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-2-tetrahydrofuryl]methyl]thio]butanoic Acid
• 2-Amino-4-({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid (non-preferred name)
• SAH;S-(5'-adenosyl)-L-homocysteine;S-adenosylhomocysteine;5'-Deoxy-S-Adenosyl-L-Homocystmine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1993	P26358	DNA (cytosine-5)-methyltransferase 1	200 nM	IC50	via Super-PRED
CHEMBL5406	Q86X55	Histone-arginine methyltransferase CARM1	400 nM	Ki	via Super-PRED
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	150 nM; 170 nM	Kd; IC50	via Super-PRED; via Super-PRED
CHEMBL6032	Q96KQ7	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	570 nM	Ki	via Super-PRED
CHEMBL6031	Q9H9B1	Histone-lysine N-methyltransferase, H3 lysine-9 specific 5	230 nM	IC50	via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	125.9 nM	Potency	via Super-PRED
CHEMBL2169716	Q9NRG4	N-lysine methyltransferase SMYD2	180 nM	IC50	via Super-PRED
CHEMBL3137261	O14744	PRMT5/MEP50 complex	560 nM	IC50	via Super-PRED
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	420 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.23%	96.09%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	92.62%	95.48%
CHEMBL4040	P28482	MAP kinase ERK2	92.11%	83.82%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	87.39%	80.33%
CHEMBL3589	P55263	Adenosine kinase	87.13%	98.05%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.28%	99.17%
CHEMBL2581	P07339	Cathepsin D	84.54%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.63%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.24%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	83.15%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.10%	91.11%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	80.76%	88.84%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.29%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	80.26%	94.73%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 193
• LOTUS: LTS0150596
• wikiData: Q105378171