Adenosine 3',5'-diphosphate

Details

• Internal ID: 27134407-57e0-4cb3-a637-2df090394039
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Purine ribonucleotides > Purine ribonucleoside 3,5-bisphosphates
• IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(phosphonooxymethyl)oxolan-3-yl] dihydrogen phosphate
• InChI: InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(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: WHTCPDAXWFLDIH-KQYNXXCUSA-N
• Popularity: 501 references 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: -4.60
• Atomic LogP (AlogP): -1.75
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• adenosine 3',5'-bisphosphate
• 1053-73-2
• adenosine-3'-5'-diphosphate
• 3',5'-ADP
• Adenosine 3'-phosphate-5'-phosphate
• phosphoadenosine phosphate
• adenosine 3',5'-bismonophosphate
• 3'-Phosphoadenylate
• 3'-Phosphoryl-AMP
• 3'-Phosphoadenosine 5'-phosphate
• [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(phosphonooxymethyl)oxolan-3-yl] dihydrogen phosphate
• CHEBI:17985
• C65F80D52U
• [5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-oxolan-2-yl]methoxyphosphonic acid
• adenosine 3',5'-bis(dihydrogen phosphate)
• 3'-Adenylic acid, 5'-(dihydrogen phosphate)
• 1vkj
• ((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
• A3P
• adenosine-3'-5'-bisphosphate
• Adenosine 3,5-bis
• 1hi4
• 1o0f
• 3,5-Diphosphoadenosine
• 3',5'-diphosphoadenosine
• Adenosine 3,5-bisphosphate
• A3P5P
• SCHEMBL42104
• UNII-C65F80D52U
• 3-Phosphoadenosine 5-phosphate
• CHEMBL574817
• GTPL1718
• 3,5-ADP
• DTXSID50909413
• 5-(dihydrogen phosphate) 3-Adenylate
• DB01812
• 5-(dihydrogen phosphate)3'-Adenylic acid
• C00054
• Q2825485
• {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5986	59.86%
Caco-2	-	0.9067	90.67%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4103	41.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9528	95.28%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8990	89.90%
P-glycoprotein inhibitior	-	0.6987	69.87%
P-glycoprotein substrate	-	0.7664	76.64%
CYP3A4 substrate	+	0.5268	52.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8652	86.52%
CYP3A4 inhibition	-	0.9247	92.47%
CYP2C9 inhibition	-	0.9329	93.29%
CYP2C19 inhibition	-	0.9311	93.11%
CYP2D6 inhibition	-	0.9113	91.13%
CYP1A2 inhibition	-	0.9157	91.57%
CYP2C8 inhibition	-	0.7291	72.91%
CYP inhibitory promiscuity	-	0.9660	96.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5430	54.30%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9484	94.84%
Skin irritation	-	0.7632	76.32%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7041	70.41%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	+	0.5266	52.66%
skin sensitisation	-	0.8504	85.04%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8084	80.84%
Acute Oral Toxicity (c)	III	0.5930	59.30%
Estrogen receptor binding	+	0.6903	69.03%
Androgen receptor binding	-	0.7342	73.42%
Thyroid receptor binding	+	0.5571	55.71%
Glucocorticoid receptor binding	-	0.7210	72.10%
Aromatase binding	+	0.6476	64.76%
PPAR gamma	+	0.5966	59.66%
Honey bee toxicity	-	0.7671	76.71%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.5892	58.92%

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	98.44%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	97.27%	80.33%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	93.46%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	90.39%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.45%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.06%	89.00%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	85.56%	94.01%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.35%	95.89%
CHEMBL3891	P07384	Calpain 1	83.01%	93.04%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.74%	95.48%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.59%	99.23%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.06%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	80.81%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.32%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 159296
• LOTUS: LTS0192555
• wikiData: Q2825485