Tocladesine

Details

• Internal ID: 11b4fe67-dedf-4972-9806-d01d34fa9f33
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Cyclic purine nucleotides > 3,5-cyclic purine nucleotides
• IUPAC Name: (4aR,6R,7R,7aS)-6-(6-amino-8-chloropurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• SMILES (Canonical): C1C2C(C(C(O2)N3C4=NC=NC(=C4N=C3Cl)N)O)OP(=O)(O1)O
• SMILES (Isomeric): C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=NC=NC(=C4N=C3Cl)N)O)OP(=O)(O1)O
• InChI: InChI=1S/C10H11ClN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
• InChI Key: CLLFEJLEDNXZNR-UUOKFMHZSA-N
• Popularity: 334 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₁ClN₅O₆P
• Molecular Weight: 363.65 g/mol
• Exact Mass: 363.0135478 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -0.16
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 8-Chloro-cAMP
• 8-Cl-cAMP
• 41941-56-4
• 8-Chloroadenosine 3',5'-monophosphate
• 8-chloro-cyclic AMP
• ICN-1256
• CCRIS 846
• UNII-BQ94Z7E5OR
• NCS 614491
• NSC-614491
• 8-Chloro-cyclic adenosine monophosphate
• BQ94Z7E5OR
• C10H11ClN5O6P
• Tocladesine [USAN:INN:BAN]
• 8-chloroadenosine 3',5'-cyclic monophosphate
• NSC-284751
• 8-Chloroadenosine 3',5'-cyclic phosphate
• Adenosine, 8-chloro-, cyclic 3',5'-(hydrogen phosphate)
• 8-Chloroadenosine 3',5'-cyclic-monophosphate
• 8-Chloroadenosine-cyclic-3',5'-monophosphate dihydrate
• C10-H11-Cl-N5-O6-P
• ADENAZOLE
• NSC614491
• 8-Chloroadenosine-3',5'-O-monophosphate
• TOCLADESINE [INN]
• Tocladesine (USAN/INN)
• TOCLADESINE [USAN]
• SCHEMBL125595
• CHEMBL2107085
• DTXSID101024678
• CN1256
• AKOS040749661
• CN 1256
• DB13046
• NSC 614491
• (4aR,6R,7R,7aS)-6-(6-amino-8-chloropurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• LS-15107
• HY-123396
• D06173
• 8-CHLOROADENOSINE-cyclic-3',5'-MONOPHOSPHATE
• W-202723
• 8-CHLORO-CYCLIC ADENOSINE 3',5'-MONOPHOSPHATE
• Q27274811
• (4aR,6R,7R,7aS)-6-(6-amino-8-chloro-purin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• (4AR,6R,7R,7AS)-6-(6-AMINO-8-CHLORO-PURIN-9-YL)-2-OXO-TETRAHYDRO-2LAMBDA*5*-FURO(3,2-D)(1,3,2)DIOXAPHOSPHININE-2,7-DIOL
• 4H-Furo[3,2-d]-1,3,2-dioxaphosphorin-7-ol, 6-(6-amino-8-chloro-9H-purin-9-yl)tetrahydro-2-hydroxy-, 2-oxide, (4aR,6R,7R,7aS)-
• 6-(6-amino-8-chloropurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9225	92.25%
Caco-2	-	0.8794	87.94%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4126	41.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9262	92.62%
OATP1B3 inhibitior	+	0.9413	94.13%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9464	94.64%
P-glycoprotein inhibitior	-	0.8431	84.31%
P-glycoprotein substrate	-	0.6641	66.41%
CYP3A4 substrate	+	0.5903	59.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	-	0.8127	81.27%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.8345	83.45%
CYP2D6 inhibition	-	0.9089	90.89%
CYP1A2 inhibition	-	0.7910	79.10%
CYP2C8 inhibition	-	0.5695	56.95%
CYP inhibitory promiscuity	-	0.8177	81.77%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5179	51.79%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9564	95.64%
Skin irritation	-	0.7693	76.93%
Skin corrosion	-	0.9270	92.70%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9247	92.47%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	+	0.5962	59.62%
skin sensitisation	-	0.8474	84.74%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5867	58.67%
Acute Oral Toxicity (c)	III	0.5511	55.11%
Estrogen receptor binding	+	0.7874	78.74%
Androgen receptor binding	-	0.6040	60.40%
Thyroid receptor binding	+	0.7415	74.15%
Glucocorticoid receptor binding	-	0.6934	69.34%
Aromatase binding	+	0.7340	73.40%
PPAR gamma	+	0.7402	74.02%
Honey bee toxicity	-	0.7290	72.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.7226	72.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	96.23%	95.48%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	95.66%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.92%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.48%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.66%	94.00%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	87.54%	92.38%
CHEMBL3384	Q16512	Protein kinase N1	86.48%	80.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.29%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.62%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.53%	97.09%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.53%	100.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.05%	94.42%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.95%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.85%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.80%	99.23%
CHEMBL3589	P55263	Adenosine kinase	81.21%	98.05%

Plants that contains it

• Ziziphus jujuba

Cross-Links

• PubChem: 100299
• NPASS: NPC224076
• ChEMBL: CHEMBL2107085