S-adenosyl-L-homocysteine

Details

• Internal ID: 987c8c8e-7166-48bd-9638-6cadcec182c6
• Taxonomy: Nucleosides, nucleotides, and analogues > 5-deoxyribonucleosides > 5-deoxy-5-thionucleosides
• IUPAC Name: (2S)-2-amino-4-[[(2S,3S,4R,5R)-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)[C@H]3[C@@H]([C@@H]([C@H](O3)CSCC[C@@H](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)/t6-,7+,9+,10+,13+/m0/s1
• InChI Key: ZJUKTBDSGOFHSH-WFMPWKQPSA-N
• Popularity: 5,670 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
• Atomic LogP (AlogP): -1.44
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• S-adenosyl-L-homocysteine
• 979-92-0
• AdoHcy
• S-(5'-adenosyl)-L-homocysteine
• S-(5'-deoxyadenosin-5'-yl)-L-homocysteine
• adenosylhomocysteine
• Formycinylhomocysteine
• 5'-Deoxy-S-adenosyl-L-homocysteine
• Adenosyl-L-homocysteine
• L-Homocysteine, S-(5'-deoxyadenosin-5'-yl)-
• 2-S-adenosyl-L-homocysteine
• SAH
• S-adenosyl-homocysteine
• L-S-Adenosylhomocysteine
• adenosylhomo-cys
• adenosyl-homo-cys
• BRN 5166233
• (S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine
• S-(5'-Deoxyadenosine-5')-L-homocysteine
• CHEMBL418052
• CHEBI:16680
• 8K31Q2S66S
• D-Ribitol, 5-S-(3-amino-3-carboxypropyl)-1-C-(7-amino-1H-pyrazolo(4,3-d)pyrimidin-3-yl)-1,4-anhydro-5-thio-, (1S,5(S))-
• S-[1-(adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl]-L-homocysteine
• (2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
• S-Adenosyl Homocysteine
• MFCD00037388
• C14H20N6O5S
• SAH (S-Adenosylhomocysteine)
• UNII-8K31Q2S66S
• 1aqi
• 1jqd
• 1qan
• 2bqz
• EINECS 213-560-8
• 1nw7
• 1s4d
• L-S-adenosyl-Homocysteine
• bmse000289
• SCHEMBL8836
• GTPL5265
• DTXSID30895860
• 2h23
• S-Adenosyl-L-homocysteine (SAH)
• S-(5''-adenosyl)-L-homocysteine
• BDBM50009672
• AKOS022184395
• CCG-208703
• DB01752
• NCGC00263623-01
• NCGC00263623-02
• NCGC00263623-03
• AS-64957
• HY-19528
• S-(((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-L-homocysteine
• S-ADENOSYL-L-HOMOCYSTEINE [USP-RS]
• CS-0015632
• FT-0771999
• Homocysteine, S-adenosyl-, L- (6CI,7CI)
• S7868
• S-(5'-Adenosyl)-L-homocysteine, crystalline
• C00021
• S-(5''-deoxyadenosin-5''-yl)-L-homocysteine
• US8895245, S-Adenosyl-L-homocysteine (SAH)
• A858597
• Q307434
• 5'-S-(3-amino-3-carboxypropyl)-5'-thio-L-Adenosine
• L-Homocysteine, S-(5'-deoxyadenosin-5'-yl)- (9CI)
• L-5'-S-(3-amino-3-carboxypropyl)-5'-thior-Adenosine
• adenosine, 5'-S-[(3S)-3-amino-3-carboxypropyl]-5'-thio-
• Adenosine, 5'-S-(3-amino-3-carboxypropyl)-5'-thio-, L- (8CI)
• S-Adenosyl-L-homocysteine, United States Pharmacopeia (USP) Reference Standard
• (2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid (non-preferred name)
• (S)-2-Amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid
• (S)-2-amino-4-(((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methylthio)butanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7845	78.45%
Caco-2	-	0.8795	87.95%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Nucleus	0.3476	34.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9399	93.99%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8916	89.16%
BSEP inhibitior	-	0.6445	64.45%
P-glycoprotein inhibitior	-	0.7498	74.98%
P-glycoprotein substrate	-	0.6973	69.73%
CYP3A4 substrate	+	0.5073	50.73%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8386	83.86%
CYP3A4 inhibition	-	0.9017	90.17%
CYP2C9 inhibition	-	0.9086	90.86%
CYP2C19 inhibition	-	0.8862	88.62%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	-	0.9028	90.28%
CYP2C8 inhibition	-	0.7578	75.78%
CYP inhibitory promiscuity	-	0.9323	93.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5871	58.71%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9840	98.40%
Skin irritation	-	0.7577	75.77%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	-	0.6869	68.69%
Human Ether-a-go-go-Related Gene inhibition	-	0.7440	74.40%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	-	0.7163	71.63%
skin sensitisation	-	0.8717	87.17%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.9177	91.77%
Acute Oral Toxicity (c)	III	0.6165	61.65%
Estrogen receptor binding	+	0.7379	73.79%
Androgen receptor binding	-	0.6348	63.48%
Thyroid receptor binding	+	0.6082	60.82%
Glucocorticoid receptor binding	+	0.5377	53.77%
Aromatase binding	+	0.6823	68.23%
PPAR gamma	+	0.6273	62.73%
Honey bee toxicity	-	0.8851	88.51%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.6479	64.79%

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	170 nM; 150 nM	IC50; Kd	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
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

• Solanum lycopersicum

Cross-Links

• PubChem: 439155
• LOTUS: LTS0163370
• wikiData: Q307434