Ap4A

Details

• Internal ID: 2a91b2b6-c7c7-4d83-a71d-7131e4ae84da
• Taxonomy: Nucleosides, nucleotides, and analogues > (5->5)-dinucleotides
• IUPAC Name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate
• InChI: InChI=1S/C20H28N10O19P4/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
• InChI Key: YOAHKNVSNCMZGQ-XPWFQUROSA-N
• Popularity: 517 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈N₁₀O₁₉P₄
• Molecular Weight: 836.40 g/mol
• Exact Mass: 836.04826669 g/mol
• Topological Polar Surface Area (TPSA): 434.00 Ų
• XlogP: -8.30
• Atomic LogP (AlogP): -2.45
• H-Bond Acceptor: 25
• H-Bond Donor: 10
• Rotatable Bonds: 14

Synonyms

• AppppA
• 5',5'''-Diadenosine tetraphosphate
• Ap4A
• 5542-28-9
• (ppA)2
• adenosine(5')tetraphospho(5')adenosine
• BIS(ADENOSINE)-5'-TETRAPHOSPHATE
• CHEMBL339385
• CHEBI:17422
• P(1),P(4)-bis(5'-adenosyl) tetraphosphate
• Adenosine 5'-tetraphosphate, 5'-ester with adenosine
• B4P
• P1,P4-Bis(5'-adenosyl) tetraphosphate
• bis(5'-adenosyl)tetraphosphate
• A(5')p4(5')A
• Diadenosine 5',5'''-P(sup 1),P(sup 2)-tetraphosphate
• diadenosine-tetraphosphate
• P(1), P(4)-diadenosine-5'tetraphosphate
• ADENOSINE 5'-(PENTAHYDROGEN TETRAPHOSPHATE), 5'-5'-ESTER with ADENOSINE
• SCHEMBL849869
• bis(5''-adenylyl) diphosphate
• DTXSID60203994
• BDBM50118220
• P1,P4-Diadenosine-5'-tetraphosphate
• P1,P4-bis(5'-adenosyl)tetraphosphate
• A(5'')p4(5'')A
• [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate
• P1,P4-Di(adenosin-5'-yl)tetraphosphate
• adenosine(5'')tetraphospho(5'')adenosine
• adenosine-(5')-tetraphospho-(5')-adenosine
• Diadenosine 5',5'''-P1,P4-tetraphosphate
• C01260
• P(1),P(4)-bis(5''-adenosyl) tetraphosphate
• Q27102391
• {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6304	63.04%
Caco-2	-	0.8579	85.79%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.3275	32.75%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9548	95.48%
OATP1B3 inhibitior	+	0.9470	94.70%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8309	83.09%
P-glycoprotein inhibitior	+	0.7357	73.57%
P-glycoprotein substrate	-	0.8138	81.38%
CYP3A4 substrate	+	0.5081	50.81%
CYP2C9 substrate	-	0.8110	81.10%
CYP2D6 substrate	-	0.8643	86.43%
CYP3A4 inhibition	-	0.7715	77.15%
CYP2C9 inhibition	-	0.9107	91.07%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9012	90.12%
CYP1A2 inhibition	-	0.8771	87.71%
CYP2C8 inhibition	-	0.7553	75.53%
CYP inhibitory promiscuity	-	0.8910	89.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5334	53.34%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.7641	76.41%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8184	81.84%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5986	59.86%
skin sensitisation	-	0.8491	84.91%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.7359	73.59%
Acute Oral Toxicity (c)	III	0.4581	45.81%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.7946	79.46%
Thyroid receptor binding	+	0.5944	59.44%
Glucocorticoid receptor binding	+	0.6715	67.15%
Aromatase binding	+	0.6779	67.79%
PPAR gamma	+	0.7197	71.97%
Honey bee toxicity	-	0.7491	74.91%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.4880	48.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4315	P47900	Purinergic receptor P2Y1	426 nM; 760 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	98.38%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	98.14%	80.33%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	94.33%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	93.98%	83.82%
CHEMBL2243	O00519	Anandamide amidohydrolase	91.30%	97.53%
CHEMBL3401	O75469	Pregnane X receptor	91.28%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	86.64%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.76%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.99%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.80%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.51%	89.00%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	83.05%	95.48%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.91%	86.33%
CHEMBL3891	P07384	Calpain 1	82.28%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.16%	99.23%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	82.03%	96.67%
CHEMBL5957	P21589	5'-nucleotidase	81.54%	97.78%
CHEMBL221	P23219	Cyclooxygenase-1	81.28%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.83%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.01%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 21706
• LOTUS: LTS0050301
• wikiData: Q27102391