[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-4-phosphonooxyoxolan-3-yl] dihydrogen phosphate

Details

• Internal ID: 530cf821-865e-4883-a915-74bbe4037e44
• Taxonomy: Nucleosides, nucleotides, and analogues > Ribonucleoside 3-phosphates
• IUPAC Name: [(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-4-phosphonooxyoxolan-3-yl] dihydrogen phosphate
• SMILES (Canonical): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)OP(=O)(O)O)OP(=O)(O)O)N
• SMILES (Isomeric): C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)(O)O)OP(=O)(O)O)N
• InChI: InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(25-27(20,21)22)6(4(1-16)23-10)24-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1
• InChI Key: OPKRDZWOEPBNBL-KQYNXXCUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₅N₅O₁₀P₂
• Molecular Weight: 427.20 g/mol
• Exact Mass: 427.02941569 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: -3.80
• Atomic LogP (AlogP): -1.75
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• Adenosine 2',3'-bisphosphoric acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7177	71.77%
Caco-2	-	0.8856	88.56%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.3383	33.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9525	95.25%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9465	94.65%
P-glycoprotein inhibitior	-	0.6655	66.55%
P-glycoprotein substrate	-	0.8122	81.22%
CYP3A4 substrate	-	0.5200	52.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.9230	92.30%
CYP2C9 inhibition	-	0.9168	91.68%
CYP2C19 inhibition	-	0.9201	92.01%
CYP2D6 inhibition	-	0.9078	90.78%
CYP1A2 inhibition	-	0.9103	91.03%
CYP2C8 inhibition	-	0.8192	81.92%
CYP inhibitory promiscuity	-	0.9714	97.14%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5510	55.10%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9237	92.37%
Skin irritation	-	0.7650	76.50%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6855	68.55%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	+	0.5393	53.93%
skin sensitisation	-	0.8532	85.32%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.4563	45.63%
Acute Oral Toxicity (c)	III	0.5780	57.80%
Estrogen receptor binding	+	0.6173	61.73%
Androgen receptor binding	-	0.5849	58.49%
Thyroid receptor binding	+	0.5642	56.42%
Glucocorticoid receptor binding	-	0.7607	76.07%
Aromatase binding	+	0.6165	61.65%
PPAR gamma	+	0.6314	63.14%
Honey bee toxicity	-	0.8129	81.29%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	-	0.7418	74.18%

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	98.06%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	93.61%	80.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.28%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.51%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	86.37%	94.73%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	85.46%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.76%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.55%	86.33%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	81.13%	94.01%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.09%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.89%	95.56%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	80.48%	95.48%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.16%	100.00%

Plants that contains it

• Glochidion zeylanicum

Cross-Links

• PubChem: 54162515
• NPASS: NPC71439