S-adenosylmethionine

Details

• Internal ID: 8755f543-5242-45f4-8622-238afaa226de
• Taxonomy: Nucleosides, nucleotides, and analogues > 5-deoxyribonucleosides > 5-deoxy-5-thionucleosides
• IUPAC Name: [(3S)-3-amino-3-carboxypropyl]-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium
• SMILES (Canonical): C[S+](CCC(C(=O)O)N)CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• SMILES (Isomeric): C[S+](CC[C@@H](C(=O)O)N)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• InChI: InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1
• InChI Key: MEFKEPWMEQBLKI-AIRLBKTGSA-O
• Popularity: 6,034 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃N₆O₅S+
• Molecular Weight: 399.40 g/mol
• Exact Mass: 399.14506403 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: -3.50
• Atomic LogP (AlogP): -1.92
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• S-adenosylmethionine
• Ademetionine
• AdoMet
• 485-80-3
• SAMe
• Donamet
• S-adenosyl methionine
• adenosylmethionine
• CHEBI:15414
• CHEMBL224120
• Methionine, S-adenosyl-
• S-(5'-Adenosyl)-L-methionine
• (R)-S-adenosyl-L-methionine
• (S)-S-adenosyl-L-methionine
• S-(5'-deoxyadenosin-5'-yl)-L-methionine
• S-adenosyl-methionine
• (R,S)-AdoMet
• (S,S)-AdoMet
• [(3S)-3-amino-3-carboxypropyl]-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium
• 2-S-adenosyl-L-methionine
• SAM
• NCGC00167546-02
• ademethionine
• AdoMe
• Adenosine, 5'-((L-3-amino-3-carboxypropyl)methylsulfonio)-5'-deoxy-, hydroxide, inner salt
• bmse000059
• Adenosine, 5'-[[(3S)-3-amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-
• SCHEMBL25177
• SCHEMBL59293
• (+)-[6]-Gingerol; (S)-(+)-[6]Gingerol; (S)-[6]Gingerol
• SCHEMBL599664
• S-(5-Adenosyl)-L-methionine
• GTPL4786
• CHEBI:33440
• CHEBI:33442
• DTXSID20110014
• MEFKEPWMEQBLKI-AIRLBKTGSA-O
• BDBM50513996
• AKOS025310126
• AM84912
• NCGC00167546-01
• S-Adenosylmethionine (protonated carboxy group)
• Q27115647
• Q27115649
• Q56071634
• 5'-Deoxyadenosine-5'-L-methionine disulfate ditosylate
• 5'-Deoxyadenosine-5'-L-methionine disulphate ditosylate
• (3S)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine
• [(3S)-3-amino-3-carboxypropyl](5'-deoxyadenosin-5'-yl)(methyl)sulfonium
• 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-adenosine
• (3S)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt
• (R)-[(3S)-3-amino-3-carboxypropyl](5'-deoxyadenosin-5'-yl)(methyl)sulfonium
• (S)-[(3S)-3-amino-3-carboxypropyl](5'-deoxyadenosin-5'-yl)(methyl)sulfonium
• [(3R)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
• [(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
• [1-(adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium
• 5 inverted exclamation marka-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5 inverted exclamation marka-deoxyadenosine
• 5invertedexclamationmarka-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5invertedexclamationmarka-deoxyadenosine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6786	67.86%
Caco-2	-	0.8273	82.73%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Nucleus	0.3837	38.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9377	93.77%
OATP1B3 inhibitior	+	0.9386	93.86%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9061	90.61%
BSEP inhibitior	-	0.8322	83.22%
P-glycoprotein inhibitior	-	0.7543	75.43%
P-glycoprotein substrate	-	0.6702	67.02%
CYP3A4 substrate	+	0.5165	51.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8422	84.22%
CYP3A4 inhibition	-	0.9731	97.31%
CYP2C9 inhibition	-	0.8396	83.96%
CYP2C19 inhibition	-	0.8457	84.57%
CYP2D6 inhibition	-	0.9192	91.92%
CYP1A2 inhibition	-	0.8308	83.08%
CYP2C8 inhibition	-	0.7858	78.58%
CYP inhibitory promiscuity	-	0.9647	96.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5938	59.38%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9780	97.80%
Skin irritation	-	0.7570	75.70%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.6991	69.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.7657	76.57%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8578	85.78%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.6217	62.17%
Estrogen receptor binding	+	0.6486	64.86%
Androgen receptor binding	-	0.8452	84.52%
Thyroid receptor binding	+	0.6099	60.99%
Glucocorticoid receptor binding	-	0.4776	47.76%
Aromatase binding	+	0.7150	71.50%
PPAR gamma	-	0.5374	53.74%
Honey bee toxicity	-	0.9288	92.88%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.4500	45.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.59%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.28%	96.09%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	93.29%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	90.58%	90.17%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	89.89%	95.48%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.59%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.32%	99.17%
CHEMBL2581	P07339	Cathepsin D	88.92%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.81%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.59%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.39%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.29%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.22%	94.45%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.58%	80.33%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	81.57%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.23%	89.00%
CHEMBL3589	P55263	Adenosine kinase	80.02%	98.05%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 34756
• LOTUS: LTS0014803
• wikiData: Q56071634