Compound Detail

CHEMBL418052

S-ADENOSYLHOMOCYSTEINE

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Nc1ncnc2c1ncn2[C@@H]1O[C@H](CSCC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL418052
Name	S-ADENOSYLHOMOCYSTEINE
Phase	Preclinical
Structure Type	MOL
InChI Key	ZJUKTBDSGOFHSH-WFMPWKQPSA-N

Targets

113

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

384.4

MW (Da)

-1.44

ALogP

HBA

HBD

182.6

PSA (Å²)

0.35

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C14H20N6O5S
MW	384.42
Aromatic Rings	2
Heavy Atoms	26
NP-Likeness	0.83

Activity Summary

IC50 86 meas. best 7.52

Ki 21 meas. best 6.8

Kd 6 meas. best 6.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histone-arginine methyltransferase CARM1 CHEMBL5406	IC50	7.52	7.52	30.0	1
DNA (cytosine-5)-methyltransferase 1 CHEMBL1993	IC50	7.15	6.1318	71.0	11
Protein arginine N-methyltransferase 7 CHEMBL3562175	IC50	6.96	6.96	110.0	1
Protein arginine N-methyltransferase 3 CHEMBL5891	IC50	6.96	6.26	110.0	3
Histone-lysine N-methyltransferase, H3 lysine-79 specific CHEMBL1795117	IC50	6.85	6.4875	140.0	4
Histone-lysine N-methyltransferase, H3 lysine-79 specific CHEMBL1795117	Kd	6.82	6.63	150.0	2
Histone-lysine N-methyltransferase, H3 lysine-79 specific CHEMBL1795117	Ki	6.8	6.7233	160.0	3
N-lysine methyltransferase SMYD2 CHEMBL2169716	IC50	6.75	6.75	180.0	1
Protein arginine N-methyltransferase 5 CHEMBL1795116	IC50	6.7	6.7	200.0	1
DNA (cytosine-5)-methyltransferase 3B CHEMBL6095	IC50	6.7	6.495	200.0	4
Replicase polyprotein 1ab CHEMBL4523582	IC50	6.66	6.66	220.0	1
Histone-lysine N-methyltransferase EHMT1 CHEMBL6031	IC50	6.64	6.64	230.0	1
Protein arginine N-methyltransferase 1 CHEMBL5524	IC50	6.6	6.0213	250.0	8
Histone-lysine N-methyltransferase EZH2 CHEMBL2189110	IC50	6.58	5.755	263.0	24
Protein arginine N-methyltransferase 1 CHEMBL5524	Ki	6.4	6.4	400.0	1
Histone-arginine methyltransferase CARM1 CHEMBL5406	Ki	6.4	6.235	400.0	2
Nonstructural protein 5 CHEMBL4295629	IC50	6.31	6.31	490.0	1
METTL3/METTL14 CHEMBL4106140	IC50	6.28	6.28	520.0	1
PRMT5/MEP50 complex CHEMBL3137261	IC50	6.25	6.235	560.0	2
Histone-lysine N-methyltransferase EHMT2 CHEMBL6032	Ki	6.24	6.24	570.0	1
Unchecked CHEMBL612545	Ki	6.24	5.4467	570.0	3
N6-adenosine-methyltransferase catalytic subunit CHEMBL4739695	IC50	6.23	6.23	590.0	1
MLL1-ASH2L/RbBP5/WDR5/DPY30 CHEMBL4106124	IC50	6.14	6.14	724.0	1
Histone-lysine N-methyltransferase SUV39H1 CHEMBL1795118	IC50	5.92	5.92	1200.0	1
Unchecked CHEMBL612545	IC50	5.75	5.36	1770.0	3
Histone-lysine N-methyltransferase EHMT2 CHEMBL6032	IC50	5.74	5.61	1820.0	3
Indolethylamine N-methyltransferase CHEMBL2131	Ki	5.7	5.7	2000.0	1
Histone-lysine N-methyltransferase SETDB1 CHEMBL2321646	IC50	5.66	5.66	2200.0	1
Protein arginine N-methyltransferase 6 CHEMBL1275221	IC50	5.66	5.66	2177.0	1
Histone-lysine N-methyltransferase 2A CHEMBL1293299	IC50	5.64	5.64	2300.0	1
tRNA (guanine-N(1)-)-methyltransferase CHEMBL4523934	Kd	5.48	5.48	3300.0	1
Histone-lysine N-methyltransferase SUV39H1 CHEMBL1795118	Ki	5.31	5.31	4900.0	1
tRNA (guanine-N(1)-)-methyltransferase CHEMBL4523932	Kd	5.23	5.23	5900.0	1
Histone-lysine N-methyltransferase EZH1 CHEMBL2189116	IC50	5.19	5.19	6400.0	1
Leishmania donovani CHEMBL367	Ki	5.14	5.14	7200.0	1
tRNA (guanine-N(1)-)-methyltransferase CHEMBL4523933	Kd	5.0	5.0	10100.0	1
Histone-lysine N-methyltransferase KMT5C CHEMBL2321644	IC50	5.0	5.0	10000.0	1
Histamine N-methyltransferase CHEMBL2190	Ki	4.98	4.86	10500.0	2
tRNA (cytosine(38)-C(5))-methyltransferase CHEMBL4523124	Kd	4.87	4.87	13600.0	1
Phenylethanolamine N-methyltransferase CHEMBL4617	Ki	4.85	4.85	14000.0	1
tRNA (cytosine(38)-C(5))-methyltransferase CHEMBL4523124	IC50	4.8	4.8	15800.0	1
Histone-lysine N-methyltransferase SUV39H2 CHEMBL1795177	IC50	4.66	4.58	22000.0	2
Nicotinamide N-methyltransferase CHEMBL2346486	IC50	4.58	4.515	26300.0	2
Phenylethanolamine N-methyltransferase CHEMBL2331	Ki	4.54	4.375	29000.0	2
Histone-lysine N-methyltransferase SETD7 CHEMBL5523	IC50	4.52	4.425	30000.0	2
Histone-lysine N-methyltransferase NSD2 CHEMBL3108645	IC50	4.41	4.41	39100.0	1
rRNA adenine N-6-methyltransferase CHEMBL2757	Ki	4.4	4.4	40000.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
Ka	55500.0	/M/s	Pseudomonas aeruginosa
Ka	7700.0	/M/s	Mycobacterium tuberculosis
Ka	279000.0	/M/s	Staphylococcus aureus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histone-arginine methyltransferase CARM1	IC50	=	30.0	nM	7.52	Inhibition of CARM1 (unknown origin) using histone H3 (21 to 44 residues) and SA...	38460270
DNA (cytosine-5)-methyltransferase 1	IC50	=	71.0	nM	7.15	Inhibition of recombinant human DNMT1 using poly(dl-dC) as substrate by hotspot ...	31978781
Protein arginine N-methyltransferase 7	IC50	=	110.0	nM	6.96	Inhibition of recombinant human PRMT7 using GST-GAR as substrate by hotspot assa...	31978781
Protein arginine N-methyltransferase 3	IC50	=	110.0	nM	6.96	Inhibition of recombinant human PRMT8 using histone H4 as substrate by hotspot a...	31978781
Histone-lysine N-methyltransferase, H3 lysine-79 specific	IC50	=	140.0	nM	6.85	Inhibition of DOTL1 (unknown origin) using [3H]SAM and HeLa oligo nucleosomes as...	35525212
Histone-lysine N-methyltransferase, H3 lysine-79 specific	Kd	=	150.0	nM	6.82	Binding affinity at human recombinant DOT1L catalytic domain amino acid (1 to 47...	22924785
Histone-lysine N-methyltransferase, H3 lysine-79 specific	Ki	=	160.0	nM	6.8	Competitive inhibition of recombinant human DOT1L using adenosine/deazaadenosine...	23879463
Histone-lysine N-methyltransferase, H3 lysine-79 specific	Ki	=	160.0	nM	6.8	Inhibition of human recombinant DOT1L catalytic domain amino acid (1 to 472) usi...	22924785
N-lysine methyltransferase SMYD2	IC50	=	180.0	nM	6.75	Inhibition of SMYD2 (unknown origin) by HMT assay	25746813
DNA (cytosine-5)-methyltransferase 1	IC50	=	200.0	nM	6.7	Inhibition of DNMT1 (unknown origin)	27485386
DNA (cytosine-5)-methyltransferase 3B	IC50	=	200.0	nM	6.7	Inhibition of human recombinant DNMT3b2	19364644
Protein arginine N-methyltransferase 5	IC50	=	200.0	nM	6.7	Inhibition of PRMT5 (unknown origin)	27485386
Replicase polyprotein 1ab	IC50	=	220.0	nM	6.66	Inhibition of SARS-CoV-2 nsp14 guanine-N7-methyltransferase activity	36970153
Histone-lysine N-methyltransferase, H3 lysine-79 specific	IC50	=	220.0	nM	6.66	Inhibition of human recombinant DOT1L (1 to 420 amino acids) expressed in Escher...	27485386
Histone-lysine N-methyltransferase EHMT1	IC50	=	230.0	nM	6.64	Inhibition of EHMT1 (unknown origin) by HMT assay	25746813
DNA (cytosine-5)-methyltransferase 3B	IC50	=	250.0	nM	6.6	Inhibition of human recombinant DNMT3B expressed in baculovirus-insect cell syst...	20006515
Protein arginine N-methyltransferase 1	IC50	=	250.0	nM	6.6	Inhibition of PRMT1 (unknown origin) using [3H]SAM and chicken histone 4 as subs...	35525212
Histone-lysine N-methyltransferase EZH2	IC50	=	263.0	nM	6.58	Inhibition Assay: S-Adenosyl-L-homocysteine (SAH) was serially diluted 3 fold in...	-
Histone-lysine N-methyltransferase EZH2	IC50	=	263.0	nM	6.58	Inhibition Assay: Compound 75 was serially diluted 3 fold in DMSO for 10 points ...	-
Histone-lysine N-methyltransferase EZH2	IC50	=	263.0	nM	6.58	Inhibition Assay: S-Adenosyl-L-homocysteine (SAH) was serially diluted 3 fold in...	-

Literature References

PubMed	DOI	Target Context	# Activities
31442049	10.1021/acs.jmedchem.9b00582	tRNA (guanine-N(1)-)-methyltransferase	12
35849534	10.1021/acs.jmedchem.2c00388	tRNA (cytosine(38)-C(5))-methyltransferase	8
3981540	10.1021/jm00382a016	Phenylethanolamine N-methyltransferase	6
3981540	10.1021/jm00382a016	Histamine N-methyltransferase	6
3981540	10.1021/jm00382a016	Catechol O-methyltransferase	4
722739	10.1021/jm00210a026	Phenylethanolamine N-methyltransferase	4
722739	10.1021/jm00210a026	Acetylserotonin O-methyltransferase	4
722739	10.1021/jm00210a026	No relevant target	4
722739	10.1021/jm00210a026	Histamine N-methyltransferase	4
722739	10.1021/jm00210a026	Catechol O-methyltransferase	4
1271409	10.1021/jm00227a021	Unchecked	3
17603473	10.1038/nature05981	5-methylthioadenosine/S-adenosylhomocysteine deaminase	3
17603473	10.1038/nature05981	Adenosylhomocysteinase	3
1271409	10.1021/jm00227a021	Catechol O-methyltransferase	3
22924785	10.1021/jm300917h	Histone-lysine N-methyltransferase, H3 lysine-79 specific	3
25746813	10.1016/j.bmcl.2015.02.017	Histone-lysine N-methyltransferase EZH2	3
39250434	10.1021/acs.jmedchem.4c00490	Protein arginine N-methyltransferase 1	3
33147410	10.1021/acs.jmedchem.0c01475	Phenylethanolamine N-methyltransferase	3
21958292	10.1021/jm2010404	DNA (cytosine-5)-methyltransferase 1	2
18083524	10.1016/j.bmc.2007.11.075	Unchecked	2

Data from ChEMBL 36 via Core Engine