5'-Sulfamoyl-2-chloroadenosine

Details

• Internal ID: ccc58db1-9175-4016-bc4d-7be3e22691bf
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides
• IUPAC Name: [(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate
• SMILES (Canonical): C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)COS(=O)(=O)N)O)O)Cl)N
• SMILES (Isomeric): C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COS(=O)(=O)N)O)O)Cl)N
• InChI: InChI=1S/C10H13ClN6O6S/c11-10-15-7(12)4-8(16-10)17(2-14-4)9-6(19)5(18)3(23-9)1-22-24(13,20)21/h2-3,5-6,9,18-19H,1H2,(H2,12,15,16)(H2,13,20,21)/t3-,5-,6-,9-/m1/s1
• InChI Key: JHUGCRSKMUFKHR-UUOKFMHZSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₃ClN₆O₆S
• Molecular Weight: 380.77 g/mol
• Exact Mass: 380.0305810 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.10
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• AT-265
• 5'-Sulfamoyl-2-chloroadenosine
• 2-chloro-5'-o-sulfamoyladenosine
• AT 265
• dealanylascamycin
• CHEMBL3250749
• [(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate
• Antibiotic AT 265
• 2-Chloroadenosine 5'-sulfamate
• Adenosine, 2-chloro-, 5'-sulfamate
• Adenosine, 2-chloro-, 5'-sulfamate (ester)
• SCHEMBL2489469
• DTXSID40985140
• 5'-O-sulfamoyl 2-chloroadenosine
• AT265
• BDBM50462455
• NSC797393
• NSC-797393
• A51191
• 2-Chloro-9-(5-O-sulfamoylpentofuranosyl)-9H-purin-6-amine
• ((2R,3S,4R,5R)-5-(6-Amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamate
• ((2R,3S,4R,5R)-5-(6-Amino-2-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methylsulfamate
• EO7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7950	79.50%
Caco-2	-	0.8951	89.51%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.3115	31.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9434	94.34%
OATP1B3 inhibitior	+	0.9386	93.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8721	87.21%
P-glycoprotein inhibitior	-	0.7887	78.87%
P-glycoprotein substrate	-	0.8458	84.58%
CYP3A4 substrate	+	0.5195	51.95%
CYP2C9 substrate	-	0.8110	81.10%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.7741	77.41%
CYP2C9 inhibition	-	0.7832	78.32%
CYP2C19 inhibition	-	0.7574	75.74%
CYP2D6 inhibition	-	0.8571	85.71%
CYP1A2 inhibition	-	0.7462	74.62%
CYP2C8 inhibition	-	0.7499	74.99%
CYP inhibitory promiscuity	-	0.8886	88.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.5900	59.00%
Carcinogenicity (trinary)	Non-required	0.5942	59.42%
Eye corrosion	-	0.9780	97.80%
Eye irritation	-	0.9807	98.07%
Skin irritation	-	0.7600	76.00%
Skin corrosion	-	0.9133	91.33%
Ames mutagenesis	-	0.6728	67.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.7277	72.77%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.6253	62.53%
skin sensitisation	-	0.8314	83.14%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6962	69.62%
Acute Oral Toxicity (c)	III	0.5836	58.36%
Estrogen receptor binding	+	0.6683	66.83%
Androgen receptor binding	+	0.5974	59.74%
Thyroid receptor binding	+	0.6827	68.27%
Glucocorticoid receptor binding	+	0.5772	57.72%
Aromatase binding	+	0.8272	82.72%
PPAR gamma	+	0.6304	63.04%
Honey bee toxicity	-	0.8311	83.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5752	57.52%
Fish aquatic toxicity	+	0.8470	84.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	167 nM	Ki	via Super-PRED
CHEMBL205	P00918	Carbonic anhydrase II	65.2 nM	Ki	via Super-PRED
CHEMBL3729	P22748	Carbonic anhydrase IV	234 nM	Ki	via Super-PRED
CHEMBL3594	Q16790	Carbonic anhydrase IX	143 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	98.84%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	94.59%	94.73%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	93.64%	80.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.51%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.45%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.24%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.95%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.34%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.83%	95.56%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	86.79%	88.84%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	86.69%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.16%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.80%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.20%	86.33%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.16%	96.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.47%	97.09%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.29%	96.90%
CHEMBL3384	Q16512	Protein kinase N1	80.07%	80.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 125623
• LOTUS: LTS0071305
• wikiData: Q76009836