2',3'-DI-O-Acetyl-5'-deoxy-5-fluorocytidine

Details

• Internal ID: a6866940-ada2-4433-8c54-8a700c6e7f96
• Taxonomy: Nucleosides, nucleotides, and analogues > 5-deoxyribonucleosides
• IUPAC Name: [(2R,3R,4R,5R)-4-acetyloxy-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-2-methyloxolan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(O1)N2C=C(C(=NC2=O)N)F)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(=NC2=O)N)F)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H16FN3O6/c1-5-9(22-6(2)18)10(23-7(3)19)12(21-5)17-4-8(14)11(15)16-13(17)20/h4-5,9-10,12H,1-3H3,(H2,15,16,20)/t5-,9-,10-,12-/m1/s1
• InChI Key: NWJBWNIUGNXJGO-RPULLILYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆FN₃O₆
• Molecular Weight: 329.28 g/mol
• Exact Mass: 329.10231340 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.25
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 5'-Deoxy-2',3'-di-O-acetyl-5-fluorocytidine
• 2',3'-DI-O-ACETYL-5'-DEOXY-5-FLUOROCYTIDINE
• Cytidine, 5'-deoxy-5-fluoro-, 2',3'-diacetate
• C13H16FN3O6
• UNII-Q6KTK8KQR2
• Q6KTK8KQR2
• [(2R,3R,4R,5R)-4-acetyloxy-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-2-methyloxolan-3-yl] acetate
• 2,3-Di-O-Acetyl-5-Deoxy-5-Fuluro-D-Cytidine
• EC 605-260-4
• 2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine
• 2', 3'-Di-O-acetyl-5'-Deoxy-5-Fluoro-D-Cytidine
• 1-(2,3-Di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-4-amino-5-fluoropyrimidin-2(1H)-one
• MFCD07369302
• (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyltetrahydrofuran-3,4-diyl diacetate
• 2'',3''-Di-O-acetyl-5''-deoxy-5-fuluro-D-cytidine
• SCHEMBL935809
• DTXSID40167207
• NWJBWNIUGNXJGO-RPULLILYSA-N
• AKOS015966242
• GS-3732
• 2,3-Di-O-acetyl-5-deoxy-5-fluorocytidine
• 2,3-di-O-acetyl-5-deoxy-5-fulurocytidine
• 5-Deoxy-2,3-di-O-acetyl-5-fluorocytidine
• CS-0158243
• 2',3'-di-o-acetyl-5'-deoxy-5-fluoro-cytidine
• A810277
• W-60381
• 2/',3/'-DI-O-Acetyl-5/'-deoxy-5-fluorocytidine
• Q63398171
• (2r,3r,4r,5r)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2h)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
• (2R,3R,4R,5R)-4-(acetyloxy)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydropyrimidin-1-yl)-2-methyloxolan-3-yl acetate
• Acetic acid 4-acetoxy-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2-methyl-tetrahydro-furan-3-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9665	96.65%
Caco-2	-	0.5893	58.93%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Lysosomes	0.6372	63.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9207	92.07%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8238	82.38%
P-glycoprotein inhibitior	-	0.6489	64.89%
P-glycoprotein substrate	-	0.7696	76.96%
CYP3A4 substrate	-	0.5320	53.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9058	90.58%
CYP3A4 inhibition	-	0.8725	87.25%
CYP2C9 inhibition	-	0.7106	71.06%
CYP2C19 inhibition	-	0.6895	68.95%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.8225	82.25%
CYP2C8 inhibition	-	0.9568	95.68%
CYP inhibitory promiscuity	-	0.8886	88.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7538	75.38%
Carcinogenicity (trinary)	Non-required	0.4911	49.11%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.8695	86.95%
Skin irritation	-	0.8220	82.20%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.5702	57.02%
Human Ether-a-go-go-Related Gene inhibition	-	0.4257	42.57%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.5254	52.54%
skin sensitisation	-	0.8912	89.12%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6504	65.04%
Acute Oral Toxicity (c)	III	0.7016	70.16%
Estrogen receptor binding	+	0.7805	78.05%
Androgen receptor binding	-	0.6301	63.01%
Thyroid receptor binding	+	0.5556	55.56%
Glucocorticoid receptor binding	-	0.6446	64.46%
Aromatase binding	+	0.6647	66.47%
PPAR gamma	+	0.5215	52.15%
Honey bee toxicity	-	0.9126	91.26%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5750	57.50%
Fish aquatic toxicity	+	0.7983	79.83%

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	97.35%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.81%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.95%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.39%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	89.15%	94.42%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.63%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	83.88%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.59%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.34%	92.94%
CHEMBL3384	Q16512	Protein kinase N1	82.96%	80.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.63%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.10%	82.69%

Plants that contains it

• Gymnosporia acuminata

Cross-Links

• PubChem: 11809635
• NPASS: NPC127416