Adenosine-5'-phosphosulfate

Details

• Internal ID: d1ba57d8-d1e7-44a8-bc54-61f38f288cc4
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Purine ribonucleotides > Purine ribonucleoside monophosphates
• IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfo hydrogen phosphate
• SMILES (Canonical): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OS(=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)OS(=O)(=O)O)O)O)N
• InChI: InChI=1S/C10H14N5O10PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1
• InChI Key: IRLPACMLTUPBCL-KQYNXXCUSA-N
• Popularity: 300 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄N₅O₁₀PS
• Molecular Weight: 427.29 g/mol
• Exact Mass: 427.01989983 g/mol
• Topological Polar Surface Area (TPSA): 238.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -2.04
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 5'-Adenylyl sulfate
• Adenosine 5'-phosphosulfate
• adenosine phosphosulfate
• ADENOSINE-5'-PHOSPHOSULFATE
• 485-84-7
• AMPS
• Adenosine sulfatophosphate
• Adenylylsulfate
• CHEBI:17709
• 5'-Adenylic acid, monoanhydride with sulfuric acid
• adenylyl-sulfate
• adenosine 5'-sulphatophosphate
• (((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphoric) sulfuric anhydride
• [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid
• ADX
• Adenosine 5'-sulfatophosphate
• BRN 0067726
• phosphosulfate
• Phosphosulphate
• sulfatophosphate
• adenylyl sulphate
• adenylyl-sulphate
• adenosine phosphosulphate
• Adenosine 5-Phosphosulfate
• Adenosine 5'-phosphosulphate
• 5'-adenylyl hydrogen sulfate
• 4-26-00-03628 (Beilstein Handbook Reference)
• SCHEMBL163762
• Adenosine Phosphosulfate (APS)
• CHEMBL572546
• BDBM25461
• IRLPACMLTUPBCL-KQYNXXCUSA-N
• AMP-S, BRN-0067726
• DB03708
• Adenosine-5'-phosphosulfate sodium salt
• adenylic acid monoanhydride with sulfurate
• adenylic acid monoanhydride with sulfuric acid
• C00224
• 5'-O-[(S)-hydroxy(sulfooxy)phosphoryl]adenosine
• Q356138
• 57D51844-70A4-4E5C-A9EF-DF05C8DC73A2
• [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl sulfo hydrogen phosphate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6476	64.76%
Caco-2	-	0.9005	90.05%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Plasma membrane	0.3353	33.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9388	93.88%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7316	73.16%
P-glycoprotein inhibitior	-	0.7146	71.46%
P-glycoprotein substrate	-	0.7823	78.23%
CYP3A4 substrate	+	0.5311	53.11%
CYP2C9 substrate	-	0.8099	80.99%
CYP2D6 substrate	-	0.8637	86.37%
CYP3A4 inhibition	-	0.9088	90.88%
CYP2C9 inhibition	-	0.8452	84.52%
CYP2C19 inhibition	-	0.8372	83.72%
CYP2D6 inhibition	-	0.8680	86.80%
CYP1A2 inhibition	-	0.8047	80.47%
CYP2C8 inhibition	-	0.7486	74.86%
CYP inhibitory promiscuity	-	0.9651	96.51%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.5700	57.00%
Carcinogenicity (trinary)	Non-required	0.5977	59.77%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.9713	97.13%
Skin irritation	-	0.7607	76.07%
Skin corrosion	-	0.9118	91.18%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5695	56.95%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5431	54.31%
skin sensitisation	-	0.8377	83.77%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8200	82.00%
Acute Oral Toxicity (c)	III	0.5885	58.85%
Estrogen receptor binding	+	0.6610	66.10%
Androgen receptor binding	+	0.5609	56.09%
Thyroid receptor binding	+	0.6278	62.78%
Glucocorticoid receptor binding	-	0.5077	50.77%
Aromatase binding	+	0.7812	78.12%
PPAR gamma	+	0.5721	57.21%
Honey bee toxicity	-	0.7183	71.83%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.3851	38.51%

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	98.12%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	98.06%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	94.78%	94.73%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	93.44%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	93.05%	95.93%
CHEMBL4040	P28482	MAP kinase ERK2	90.07%	83.82%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.79%	97.53%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.72%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.86%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.45%	99.23%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	83.57%	94.01%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.47%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.68%	96.00%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.64%	95.48%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.26%	89.00%
CHEMBL3891	P07384	Calpain 1	81.97%	93.04%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 10238
• LOTUS: LTS0138833
• wikiData: Q356138