[(3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-N-[9-[(3S,5S)-5-[[[[(2S,3R)-2,3-dihydroxy-4-methylpentanoyl]amino]-hydroxyphosphoryl]oxymethyl]-3-hydroxyoxolan-2-yl]purin-6-yl]phosphonamidic acid

Details

• Internal ID: 01c01d6e-b41c-4b86-8fd6-1331d094903f
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives
• IUPAC Name: [(3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-N-[9-[(3S,5S)-5-[[[[(2S,3R)-2,3-dihydroxy-4-methylpentanoyl]amino]-hydroxyphosphoryl]oxymethyl]-3-hydroxyoxolan-2-yl]purin-6-yl]phosphonamidic acid
• InChI: InChI=1S/C22H36N6O16P2/c1-8(2)13(32)15(34)20(36)27-45(37,38)41-5-9-3-10(30)21(42-9)28-7-25-12-18(23-6-24-19(12)28)26-46(39,40)44-22-16(35)14(33)17(43-22)11(31)4-29/h6-11,13-17,21-22,29-35H,3-5H2,1-2H3,(H2,27,36,37,38)(H2,23,24,26,39,40)/t9-,10-,11+,13+,14+,15-,16+,17-,21?,22?/m0/s1
• InChI Key: FIMRCGIHIAIVOL-DUQSPLRMSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆N₆O₁₆P₂
• Molecular Weight: 702.50 g/mol
• Exact Mass: 702.16630308 g/mol
• Topological Polar Surface Area (TPSA): 338.00 Ų
• XlogP: -5.00
• Atomic LogP (AlogP): -3.59
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 14

Synonyms

• [(3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-N-[9-[(3S,5S)-5-[[[[(2S,3R)-2,3-dihydroxy-4-methylpentanoyl]amino]-hydroxyphosphoryl]oxymethyl]-3-hydroxyoxolan-2-yl]purin-6-yl]phosphonamidic acid
• SCHEMBL29885409

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6314	63.14%
Caco-2	-	0.8766	87.66%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Lysosomes	0.3818	38.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8825	88.25%
OATP1B3 inhibitior	+	0.9401	94.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6727	67.27%
P-glycoprotein inhibitior	+	0.6583	65.83%
P-glycoprotein substrate	+	0.6691	66.91%
CYP3A4 substrate	+	0.6695	66.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8665	86.65%
CYP3A4 inhibition	-	0.8438	84.38%
CYP2C9 inhibition	-	0.8932	89.32%
CYP2C19 inhibition	-	0.8936	89.36%
CYP2D6 inhibition	-	0.8361	83.61%
CYP1A2 inhibition	-	0.7885	78.85%
CYP2C8 inhibition	+	0.5096	50.96%
CYP inhibitory promiscuity	-	0.9342	93.42%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5593	55.93%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.9198	91.98%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7065	70.65%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	-	0.5669	56.69%
skin sensitisation	-	0.8390	83.90%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8134	81.34%
Acute Oral Toxicity (c)	III	0.5146	51.46%
Estrogen receptor binding	+	0.7250	72.50%
Androgen receptor binding	+	0.6621	66.21%
Thyroid receptor binding	+	0.5703	57.03%
Glucocorticoid receptor binding	+	0.6034	60.34%
Aromatase binding	+	0.6231	62.31%
PPAR gamma	+	0.6473	64.73%
Honey bee toxicity	-	0.7214	72.14%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.6798	67.98%

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	99.16%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.53%	85.14%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	93.34%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	93.24%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.48%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	92.12%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.83%	91.11%
CHEMBL2243	O00519	Anandamide amidohydrolase	91.05%	97.53%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.59%	89.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	90.36%	82.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.63%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.58%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.57%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	88.24%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.54%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.37%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.21%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.21%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.17%	97.25%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.89%	90.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.43%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.32%	94.33%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.31%	92.86%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.82%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.17%	89.62%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.83%	89.34%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	81.95%	99.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.91%	95.83%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.65%	97.29%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.91%	93.10%
CHEMBL5028	O14672	ADAM10	80.79%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.31%	93.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 3035458
• LOTUS: LTS0009069
• wikiData: Q105105116