2-Amino-9-[5-o-(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)pentofuranosyl]-3,9-dihydro-6h-purin-6-one

Details

• Internal ID: a5346dfb-22b9-45d2-92da-fde52be6e9ee
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Purine ribonucleotides > Purine ribonucleoside triphosphates
• IUPAC Name: [[5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• SMILES (Canonical): C1=NC2=C(N1C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O)N=C(NC2=O)N
• SMILES (Isomeric): C1=NC2=C(N1C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O)N=C(NC2=O)N
• InChI: InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)
• InChI Key: XKMLYUALXHKNFT-UHFFFAOYSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆N₅O₁₄P₃
• Molecular Weight: 523.18 g/mol
• Exact Mass: 522.99066119 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: -5.70
• Atomic LogP (AlogP): -2.34
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• 2-amino-9-[5-o-(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)pentofuranosyl]-3,9-dihydro-6h-purin-6-one
• 2-Amino-9-(5-O-(hydroxy((hydroxy(phosphonooxy)phosphoryl)oxy)phosphoryl)pentofuranosyl)-3,9-dihydro-6H-purin-6-one
• RefChem:1062213
• DTXCID60202780
• MolMap_000068
• SCHEMBL4368666
• SCHEMBL18271799
• BDBM86059
• CAS_6830
• NSC_6830
• L001001
• (5-(2-Amino-6-oxo-1H-purin-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
• [[(2S,3R,4R,5R)-5-(2-Amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5926	59.26%
Caco-2	-	0.8861	88.61%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4074	40.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9316	93.16%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6306	63.06%
P-glycoprotein inhibitior	-	0.4895	48.95%
P-glycoprotein substrate	-	0.7062	70.62%
CYP3A4 substrate	+	0.5647	56.47%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8690	86.90%
CYP3A4 inhibition	-	0.9501	95.01%
CYP2C9 inhibition	-	0.9277	92.77%
CYP2C19 inhibition	-	0.9263	92.63%
CYP2D6 inhibition	-	0.9013	90.13%
CYP1A2 inhibition	-	0.8523	85.23%
CYP2C8 inhibition	-	0.7868	78.68%
CYP inhibitory promiscuity	-	0.9833	98.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5194	51.94%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9550	95.50%
Skin irritation	-	0.7624	76.24%
Skin corrosion	-	0.9252	92.52%
Ames mutagenesis	-	0.6882	68.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.4530	45.30%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	+	0.5617	56.17%
skin sensitisation	-	0.8400	84.00%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.4683	46.83%
Acute Oral Toxicity (c)	III	0.6434	64.34%
Estrogen receptor binding	+	0.7219	72.19%
Androgen receptor binding	+	0.7740	77.40%
Thyroid receptor binding	+	0.5537	55.37%
Glucocorticoid receptor binding	-	0.5325	53.25%
Aromatase binding	+	0.8148	81.48%
PPAR gamma	+	0.6000	60.00%
Honey bee toxicity	-	0.7465	74.65%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.4786	47.86%

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	98.11%	83.82%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	97.76%	80.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.68%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.98%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.03%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	91.53%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.82%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.32%	97.09%
CHEMBL5957	P21589	5'-nucleotidase	85.18%	97.78%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	85.09%	95.48%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	84.67%	88.84%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.12%	95.64%
CHEMBL1952	P04818	Thymidylate synthase	83.86%	93.53%
CHEMBL2094108	P49354	Protein farnesyltransferase	82.39%	97.92%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.26%	93.10%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.24%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.55%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.49%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.38%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.32%	89.34%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.23%	96.12%

Plants that contains it

• Helianthus tuberosus

Cross-Links

• PubChem: 135400627
• LOTUS: LTS0040539
• wikiData: Q105329574