(2S,3S,4S,5R,6R)-6-[[[(2S,3S,4S,5S)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: 5f4b763d-bcc1-4008-999d-1ef8486a935e
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine nucleotide sugars
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[[(2S,3S,4S,5S)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)C(=O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CN(C(=O)NC1=O)[C@@H]2[C@H]([C@@H]([C@@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O)O)O
• InChI: InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6+,7-,8-,9-,10+,11-,12-,14+/m0/s1
• InChI Key: HDYANYHVCAPMJV-JTFFWVQGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂N₂O₁₈P₂
• Molecular Weight: 580.28 g/mol
• Exact Mass: 580.03428585 g/mol
• Topological Polar Surface Area (TPSA): 309.00 Ų
• XlogP: -6.40
• Atomic LogP (AlogP): -4.70
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9535	95.35%
Caco-2	-	0.8936	89.36%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5497	54.97%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9183	91.83%
OATP1B3 inhibitior	+	0.9402	94.02%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6723	67.23%
P-glycoprotein inhibitior	-	0.4944	49.44%
P-glycoprotein substrate	-	0.8445	84.45%
CYP3A4 substrate	+	0.5966	59.66%
CYP2C9 substrate	-	0.5958	59.58%
CYP2D6 substrate	-	0.8684	86.84%
CYP3A4 inhibition	-	0.7204	72.04%
CYP2C9 inhibition	-	0.8764	87.64%
CYP2C19 inhibition	-	0.8316	83.16%
CYP2D6 inhibition	-	0.8742	87.42%
CYP1A2 inhibition	-	0.8670	86.70%
CYP2C8 inhibition	-	0.5882	58.82%
CYP inhibitory promiscuity	-	0.8237	82.37%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5032	50.32%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9365	93.65%
Skin irritation	-	0.7873	78.73%
Skin corrosion	-	0.9339	93.39%
Ames mutagenesis	-	0.7678	76.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.3795	37.95%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.5763	57.63%
skin sensitisation	-	0.8566	85.66%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8124	81.24%
Acute Oral Toxicity (c)	III	0.5847	58.47%
Estrogen receptor binding	+	0.6745	67.45%
Androgen receptor binding	+	0.7678	76.78%
Thyroid receptor binding	+	0.5186	51.86%
Glucocorticoid receptor binding	-	0.4737	47.37%
Aromatase binding	+	0.5505	55.05%
PPAR gamma	+	0.6851	68.51%
Honey bee toxicity	-	0.7373	73.73%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7172	71.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4518	Q15391	Purinergic receptor P2Y14	370 nM; 370 nM	EC50; EC50	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.74%	96.09%
CHEMBL2123	P51582	Pyrimidinergic receptor P2Y4	92.57%	93.39%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	89.40%	87.67%
CHEMBL2581	P07339	Cathepsin D	87.87%	98.95%
CHEMBL5957	P21589	5'-nucleotidase	86.97%	97.78%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.20%	80.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.17%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	84.25%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.54%	86.92%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.34%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.40%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	82.35%	95.93%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.20%	91.71%
CHEMBL4040	P28482	MAP kinase ERK2	81.01%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.96%	99.23%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 163013618
• LOTUS: LTS0029720
• wikiData: Q105026667