Adenosine-5'-diphosphate

Details

• Internal ID: ef6a99a7-eb25-41a2-af41-b879708d2492
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Purine ribonucleotides > Purine ribonucleoside diphosphates
• IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate
• SMILES (Canonical): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)O)O)O)N
• SMILES (Isomeric): C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)O)O)O)N
• InChI: InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
• InChI Key: XTWYTFMLZFPYCI-KQYNXXCUSA-N
• Popularity: 37,089 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: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• Adenosine diphosphate
• 58-64-0
• adenosine-5'-diphosphate
• ADP
• Adenosine 5'-(trihydrogen diphosphate)
• adenosine pyrophosphate
• 5'-Adp
• adenosine 5'-pyrophosphate
• ADP (nucleotide)
• 5'-Adenylphosphoric acid
• Adenosindiphosphorsaeure
• Adenosine 5'-pyrophosphoric acid
• Adenosine-5'-diphosphat
• Adenosine 5'-diphosphoric acid
• Adenosine diphosphoric acid
• Ado-5'-P-P
• H3adp
• adenosine-5-diphosphate
• BRN 0067722
• 110123-09-6
• CHEBI:16761
• adenosine 5' diphosphate
• ADENOSINE, 5'-(TRIHYDROGEN PYROPHOSPHATE)
• 61D2G4IYVH
• CHEMBL14830
• [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate
• 20398-34-9
• Adenosine-5'-Diphosphate, free acid
• 1,4-Cyclohexadiene-3,3,6,6-d4
• Dynorphin A (1-13), ala(2)-trp(4)-
• ((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl trihydrogen diphosphate
• 104746-05-6
• 11062-03-6
• 112360-08-4
• 17791-27-4
• 4-(3-Carboxytrimethyleneoxy)-4/'/'-octylazobenzene
• Adenosine disphosphate
• [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• Adenosine diphosphate;ADP
• Adenosine 5'-diphosphate sodium salt
• C10H15N5O10P2
• EINECS 200-392-5
• UNII-61D2G4IYVH
• 1amw
• 1lkx
• 1ucn
• 1xxi
• 1yrs
• 2bfr
• MFCD00066473
• a-ADP
• 1ao0
• 1e8h
• 1hi5
• 1o0h
• 1oz4
• 1t3t
• 1y8o
• Adenosine5'-diphosphate
• bmse000004
• bmse000935
• bmse000991
• Epitope ID:137351
• Adenosine Diphosphate (ADP)
• SCHEMBL24103
• Adenosine diphosphate (6CI)
• 4-26-00-03629 (Beilstein Handbook Reference)
• GTPL1712
• SCHEMBL18076199
• BDBM31995
• DTXSID60883210
• 1m74
• 2c02
• ADENOSINE DIPHOSPHATE [MI]
• BDBM50368125
• PDSP1_001088
• PDSP2_001072
• s9368
• ADENOSINE DIPHOSPHATE [WHO-DD]
• AKOS022179933
• CCG-268971
• CS-W011634
• HY-W010918
• s10970
• Adenosine, 5'-(trihydrogen diphosphate)
• NCGC00163322-01
• AC-32145
• AS-11755
• BP-58727
• Adenosine 5'-diphosphate, >=95% (HPLC)
• Adenosine diphosphate;Adenosine 5'-diphosphate
• Adenosine 5'-(trihydrogen diphosphate) (9CI)
• C00008
• Adenosine 5'-(trihydrogen pyrophosphate) (8CI)
• EN300-1588520
• Q185253
• J-700143
• 9-{5-O-[hydroxy(phosphonooxy)phosphoryl]-b-D-glycero-pentofuranosyl}-9H-purin-6-amine
• 9H-Purin-6-amine, 9-[5-O-[hydroxy(phosphonooxy)phosphinyl]-.beta.-D-ribofuranosyl]-
• 9H-purin-6-amine, 9-[5-O-[hydroxy(phosphonooxy)phosphinyl]-beta-D-glycero-pentofuranosyl]-
• [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl phosphono hydrogen phosphate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7073	70.73%
Caco-2	-	0.9126	91.26%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.3563	35.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9506	95.06%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8703	87.03%
P-glycoprotein inhibitior	-	0.7173	71.73%
P-glycoprotein substrate	-	0.8058	80.58%
CYP3A4 substrate	+	0.5249	52.49%
CYP2C9 substrate	-	0.8110	81.10%
CYP2D6 substrate	-	0.8643	86.43%
CYP3A4 inhibition	-	0.9375	93.75%
CYP2C9 inhibition	-	0.9403	94.03%
CYP2C19 inhibition	-	0.9352	93.52%
CYP2D6 inhibition	-	0.9005	90.05%
CYP1A2 inhibition	-	0.8908	89.08%
CYP2C8 inhibition	-	0.7090	70.90%
CYP inhibitory promiscuity	-	0.9760	97.60%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5574	55.74%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9732	97.32%
Skin irritation	-	0.7587	75.87%
Skin corrosion	-	0.9245	92.45%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6144	61.44%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5861	58.61%
skin sensitisation	-	0.8398	83.98%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.7647	76.47%
Acute Oral Toxicity (c)	III	0.6405	64.05%
Estrogen receptor binding	+	0.7121	71.21%
Androgen receptor binding	+	0.7867	78.67%
Thyroid receptor binding	+	0.6714	67.14%
Glucocorticoid receptor binding	-	0.5362	53.62%
Aromatase binding	+	0.8157	81.57%
PPAR gamma	+	0.5756	57.56%
Honey bee toxicity	-	0.7336	73.36%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.6008	60.08%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4315	P47900	Purinergic receptor P2Y1	24 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	98.57%	80.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.47%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.63%	83.82%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	94.26%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	91.63%	94.73%
CHEMBL2243	O00519	Anandamide amidohydrolase	89.12%	97.53%
CHEMBL226	P30542	Adenosine A1 receptor	87.05%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.76%	95.89%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	84.54%	96.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.99%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.33%	86.33%
CHEMBL2094108	P49354	Protein farnesyltransferase	83.24%	97.92%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	83.05%	95.48%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.39%	89.00%
CHEMBL3891	P07384	Calpain 1	82.28%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.16%	99.23%
CHEMBL5957	P21589	5'-nucleotidase	81.77%	97.78%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.37%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.83%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.40%	96.00%

Plants that contains it

• Arabidopsis thaliana
• Helianthus tuberosus

Cross-Links

• PubChem: 6022
• LOTUS: LTS0160855
• wikiData: Q185253