Adenosine-5'-triphosphate

Details

• Internal ID: 98cfdbd2-4a14-4638-849e-46f499474485
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Purine ribonucleotides > Purine ribonucleoside triphosphates
• IUPAC Name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• SMILES (Canonical): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=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)OP(=O)(O)O)O)O)N
• InChI: InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
• InChI Key: ZKHQWZAMYRWXGA-KQYNXXCUSA-N
• Popularity: 148,626 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆N₅O₁₃P₃
• Molecular Weight: 507.18 g/mol
• Exact Mass: 506.99574658 g/mol
• Topological Polar Surface Area (TPSA): 279.00 Ų
• XlogP: -5.70
• Atomic LogP (AlogP): -1.63
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 56-65-5
• Adenosine 5'-triphosphate
• ATP
• Triphosphaden
• adenosine-5'-triphosphate
• Myotriphos
• Striadyne
• Triadenyl
• Atriphos
• Atipi
• Glucobasin
• Adephos
• Adetol
• Adynol
• Adenosine 5'-(tetrahydrogen triphosphate)
• 5'-Atp
• Triphosaden
• Adenylpyrophosphoric acid
• Triphosphoric acid adenosine ester
• Adenosine 5'-triphosphoric acid
• ATP (nucleotide)
• Cardenosine
• Fosfobion
• Adenosintriphosphorsaeure
• Ara-ATP
• adenosine-triphosphate
• Ado-5'-P-P-P
• H4atp
• 9-beta-D-Arabinofuranosyladenine 5'-triphosphate
• CHEBI:15422
• adenylpyrophosphate
• Adenosine, 5'-(tetrahydrogen triphosphate)
• adenosine 5' triphosphate
• 126827-79-0
• 3-Methylbenzo[d]thiazol-3-iuM chloride
• CHEMBL14249
• 8L70Q75FXE
• DTXSID6022559
• ((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
• [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• 11016-17-4
• 119439-06-4
• NCGC00163309-01
• ({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• 126339-06-8
• ATP disodium salt hydrate
• Phosphobion
• 51963-61-2
• C10H16N5O13P3
• EINECS 200-283-2
• UNII-8L70Q75FXE
• MFCD00065467
• adenosine-5'-triphosphoric acid
• 1kxp
• 1mau
• 1maw
• 1vjc
• 1vjd
• 1xsc
• 1yid
• 2cbz
• 2fgh
• Adenylpyrophosphorate
• Triphosadenine (DCF)
• 1gz3
• 1gz4
• 1r0x
• 1y8p
• BDBM2
• 3h-adenosine triphosphate
• -beta-D-ribofuranosyl]-
• bmse000006
• bmse000854
• bmse000993
• Epitope ID:135612
• Adenosine 5'-triphosphorate
• SCHEMBL8979
• DTXCID302559
• GTPL1713
• 1b38
• 1b39
• 1m83
• 1r10
• 1t44
• Bio1_000406
• Bio1_000895
• Bio1_001384
• ADENOSINE TRIPHOSPHATE [MI]
• AMY22292
• HY-B2176
• Tox21_112044
• ADENOSINE TRIPHOSPHATE [INCI]
• BDBM50366480
• s5260
• ADENOSINE TRIPHOSPHATE [VANDF]
• ADENOSINE TRIPHOSPHATE [MART.]
• AKOS022179934
• ADENOSINE TRIPHOSPHATE [WHO-DD]
• CS-7674
• DB00171
• CAS-56-65-5
• Adenosine 5'-triphosphate; Triphosphaden
• [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
• 5'-(tetrahydrogen triphosphate) Adenosine
• AC-32151
• AS-19204
• C00002
• D08646
• D70159
• Q80863
• EN300-1073142
• A831137
• W-105506
• A9788C43-4BC5-46E2-8560-41C5FA7D3AA3
• 9H-purin-6-amine, 9-[5-O-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]
• [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydroxy-phosphonooxyphosphoryl) hydrogen phosphate
• [(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydroxy-phosphonooxyphosphoryl) hydrogen phosphate;((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
• [[[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxyphosphonic acid
• 9H-Purin-6-amine, 9-[5-O-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-.beta.-D-ribofuranosyl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7073	70.73%
Caco-2	-	0.8870	88.70%
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	+	0.9486	94.86%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5968	59.68%
P-glycoprotein inhibitior	-	0.5451	54.51%
P-glycoprotein substrate	-	0.7769	77.69%
CYP3A4 substrate	+	0.5348	53.48%
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	-	0.6948	69.48%
CYP inhibitory promiscuity	-	0.9760	97.60%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5574	55.74%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9565	95.65%
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	-	0.4373	43.73%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5611	56.11%
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	-	0.7286	72.86%
Acute Oral Toxicity (c)	III	0.6405	64.05%
Estrogen receptor binding	+	0.7573	75.73%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.6551	65.51%
Glucocorticoid receptor binding	-	0.4752	47.52%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.5808	58.08%
Honey bee toxicity	-	0.7306	73.06%
Biodegradation	-	0.6500	65.00%
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
CHEMBL1293235	P02545	Prelamin-A/C	5 nM	Potency	via Super-PRED
CHEMBL4315	P47900	Purinergic receptor P2Y1	150 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	98.64%	80.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.47%	96.09%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	94.26%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	92.82%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	91.63%	94.73%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.80%	97.53%
CHEMBL226	P30542	Adenosine A1 receptor	87.05%	95.93%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	84.80%	95.48%
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%
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	81.70%	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

• Helianthus tuberosus

Cross-Links

• PubChem: 5957
• LOTUS: LTS0029364
• wikiData: Q80863