methyl (1R,3R,4R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(E)-2-methylbut-2-enoyl]oxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate

Details

• Internal ID: 287e810f-e6c6-4dda-8239-c56ca0649abd
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Glycosylamines
• IUPAC Name: methyl (1R,3R,4R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(E)-2-methylbut-2-enoyl]oxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(OC2C1(OC3C(C2)OC(C3O)N4C=NC5=C(N=CN=C54)N)O)C(=O)OC)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@@H]([C@H](O[C@H]2[C@]1(O[C@H]3[C@@H](C2)OC([C@@H]3O)N4C=NC5=C(N=CN=C54)N)O)C(=O)OC)O
• InChI: InChI=1S/C22H27N5O10/c1-4-8(2)20(30)36-16-12(28)15(21(31)33-3)35-10-5-9-14(37-22(10,16)32)13(29)19(34-9)27-7-26-11-17(23)24-6-25-18(11)27/h4,6-7,9-10,12-16,19,28-29,32H,5H2,1-3H3,(H2,23,24,25)/b8-4+/t9-,10-,12-,13-,14+,15+,16+,19?,22-/m1/s1
• InChI Key: LUHFPLRYWUPHKS-LTMOQEKKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₇N₅O₁₀
• Molecular Weight: 521.50 g/mol
• Exact Mass: 521.17579208 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.68
• H-Bond Acceptor: 15
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7638	76.38%
Caco-2	-	0.8483	84.83%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Plasma membrane	0.3171	31.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9071	90.71%
OATP1B3 inhibitior	+	0.9367	93.67%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7331	73.31%
P-glycoprotein inhibitior	+	0.5746	57.46%
P-glycoprotein substrate	+	0.6749	67.49%
CYP3A4 substrate	+	0.6587	65.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8805	88.05%
CYP3A4 inhibition	-	0.8565	85.65%
CYP2C9 inhibition	-	0.7545	75.45%
CYP2C19 inhibition	-	0.7904	79.04%
CYP2D6 inhibition	-	0.8989	89.89%
CYP1A2 inhibition	-	0.8592	85.92%
CYP2C8 inhibition	+	0.5790	57.90%
CYP inhibitory promiscuity	-	0.8393	83.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4258	42.58%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9372	93.72%
Skin irritation	-	0.7820	78.20%
Skin corrosion	-	0.9343	93.43%
Ames mutagenesis	+	0.5144	51.44%
Human Ether-a-go-go-Related Gene inhibition	-	0.4857	48.57%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	-	0.5349	53.49%
skin sensitisation	-	0.8719	87.19%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6189	61.89%
Acute Oral Toxicity (c)	III	0.5983	59.83%
Estrogen receptor binding	+	0.8010	80.10%
Androgen receptor binding	+	0.5631	56.31%
Thyroid receptor binding	+	0.6528	65.28%
Glucocorticoid receptor binding	+	0.6617	66.17%
Aromatase binding	+	0.7100	71.00%
PPAR gamma	+	0.6526	65.26%
Honey bee toxicity	-	0.6711	67.11%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7281	72.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.70%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	95.14%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.40%	99.23%
CHEMBL2243	O00519	Anandamide amidohydrolase	92.95%	97.53%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.58%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.47%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	91.44%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.37%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.86%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.42%	89.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.84%	89.34%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	88.33%	95.48%
CHEMBL3401	O75469	Pregnane X receptor	88.18%	94.73%
CHEMBL2535	P11166	Glucose transporter	86.99%	98.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.58%	91.03%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	86.01%	80.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.34%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.56%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.85%	97.09%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.84%	82.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.99%	97.36%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.60%	94.42%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	81.83%	98.99%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.48%	93.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.24%	85.30%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.06%	96.90%

Plants that contains it

• Montanoa tomentosa

Cross-Links

• PubChem: 163185370
• LOTUS: LTS0045268
• wikiData: Q105116948