L-Adenosine

Details

• Internal ID: b9da6fd3-1c80-4a63-9b28-cc03e36faa9e
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: (2S,3S,4R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• SMILES (Canonical): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
• SMILES (Isomeric): C1=NC(=C2C(=N1)N(C=N2)[C@@H]3[C@H]([C@H]([C@@H](O3)CO)O)O)N
• InChI: InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m0/s1
• InChI Key: OIRDTQYFTABQOQ-DEGSGYPDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.24 g/mol
• Exact Mass: 267.09675391 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.98
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 3080-29-3
• (2S,3S,4R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• Beta-L-adenosine
• MFCD01075784
• (2S,3S,4R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• 9H-Purin-6-amine, 9-beta-L-ribofuranosyl-
• (2S,3S,4R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• (2S,3S,4R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• 9-(b-L-Ribofuranosyl)adenine
• Oprea1_180751
• 9-beta-L-Ribofuranosyladenine
• SCHEMBL329845
• NSC87676; -L-Adenosine
• 9-(?-L-Ribofuranosyl)adenine
• BDBM82533
• OIRDTQYFTABQOQ-DEGSGYPDSA-N
• SBB057547
• AKOS022186150
• NA06227
• AS-63680
• SY336869
• CAS_3080-29-3
• 9H-Purin-6-amine, 9-|A-L-ribofuranosyl-
• W16174
• F601144
• FE0ACFBC-F7F2-426A-89CC-682E8EAF057C
• (2S,3S,4R,5S)-2-(6-Amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6454	64.54%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.9429	94.29%
Subcellular localzation	Nucleus	0.4394	43.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9590	95.90%
OATP1B3 inhibitior	+	0.9512	95.12%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9555	95.55%
P-glycoprotein inhibitior	-	0.9229	92.29%
P-glycoprotein substrate	-	0.8999	89.99%
CYP3A4 substrate	-	0.6259	62.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8703	87.03%
CYP3A4 inhibition	-	0.9620	96.20%
CYP2C9 inhibition	-	0.9595	95.95%
CYP2C19 inhibition	-	0.9514	95.14%
CYP2D6 inhibition	-	0.9770	97.70%
CYP1A2 inhibition	-	0.9667	96.67%
CYP2C8 inhibition	-	0.8783	87.83%
CYP inhibitory promiscuity	-	0.9701	97.01%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5680	56.80%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9280	92.80%
Skin irritation	-	0.7595	75.95%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	-	0.8491	84.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.6454	64.54%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.8235	82.35%
skin sensitisation	-	0.8606	86.06%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8236	82.36%
Acute Oral Toxicity (c)	III	0.7890	78.90%
Estrogen receptor binding	-	0.5890	58.90%
Androgen receptor binding	+	0.6240	62.40%
Thyroid receptor binding	+	0.5830	58.30%
Glucocorticoid receptor binding	+	0.5472	54.72%
Aromatase binding	+	0.8260	82.60%
PPAR gamma	+	0.7051	70.51%
Honey bee toxicity	-	0.9226	92.26%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.9143	91.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL226	P30542	Adenosine A1 receptor	2.344 nM	IC50	via Super-PRED
CHEMBL251	P29274	Adenosine A2a receptor	700 nM	EC50	via Super-PRED
CHEMBL256	P0DMS8	Adenosine A3 receptor	1.148 nM	IC50	via Super-PRED
CHEMBL284	P27487	Dipeptidyl peptidase IV	62 nM	IC50	via Super-PRED
CHEMBL5401	P42226	Signal transducer and activator of transcription 6	0.03162 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3589	P55263	Adenosine kinase	98.93%	98.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.71%	96.09%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	95.34%	100.00%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	90.74%	80.33%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	90.27%	96.67%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	89.33%	95.48%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.04%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.36%	94.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	84.35%	98.46%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.43%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.13%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	82.01%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.74%	95.89%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.47%	88.00%

Plants that contains it

• Panax ginseng

Cross-Links

• PubChem: 448374
• NPASS: NPC197030