2'-Deoxyuridine

Details

• Internal ID: 9b372559-481d-4859-961a-e5b3879ef096
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleosides > Pyrimidine 2-deoxyribonucleosides
• IUPAC Name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• SMILES (Canonical): C1C(C(OC1N2C=CC(=O)NC2=O)CO)O
• SMILES (Isomeric): C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O
• InChI: InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1
• InChI Key: MXHRCPNRJAMMIM-SHYZEUOFSA-N
• Popularity: 4,461 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂N₂O₅
• Molecular Weight: 228.20 g/mol
• Exact Mass: 228.07462149 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.82
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 951-78-0
• deoxyuridine
• Uracil deoxyriboside
• Uridine, 2'-deoxy-
• 2-Deoxyuridine
• Deoxyribose uracil
• 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• dURD
• C9H12N2O5
• 2'-Desoxyuridine
• CCRIS 2832
• 2'-Deoxyuridine-1'-d
• EINECS 213-455-7
• NSC 23615
• BRN 0024433
• UNII-W78I7AY22C
• 1-(2-Deoxy-beta-D-ribofuranosyl)uracil
• W78I7AY22C
• CHEBI:16450
• 1-(2-Deoxy-beta-D-erythro-pentofuranoxyl)uracil
• 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-
• 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-erythro-ribofuranosyl)-
• 1-(2-deoxy-beta-D-erythro-pentofuranosyl)uracil
• 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• Desoxyuridine
• Uracil desoxyuridine
• MFCD00006527
• DUR
• NSC-23615
• 1-(2-Deoxy-D-erythro-pentofuranosyl)uracil
• Uridinie, 2'-deoxy-
• 2yb0
• DEOXYURIDINE [MI]
• bmse000320
• D00CVB
• D05IJN
• SCHEMBL28844
• MLS001066344
• 2'-dU
• CHEMBL353955
• 2'-Deoxyuridine, >=98.5%
• AMY6955
• DTXSID30883621
• MXHRCPNRJAMMIM-SHYZEUOFSA-N
• HMS2267D16
• HY-D0186
• s5505
• ZINC00155696
• AKOS015833069
• AKOS015896792
• 1-(2-Deoxy-ss-D-ribofuranosyl)uracil
• CCG-247504
• CS-W019820
• DB02256
• PS-7750
• 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-furan-2-yl)pyrimidine-2,4(1H,3H)-dione
• 1-[(4S,2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-dihydropyrimidine-2, 4-dione
• NCGC00142492-01
• (beta 1-(2-Deoxyribopyranosyl))thymidine
• BP-58660
• SMR000112296
• LS-160815
• D0060
• 1-(2-Deoxy-delta-erythro-pentofuranosyl)uracil
• C00526
• O10766
• EN300-7374520
• Q419140
• J-700048
• 1-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)URACIL
• E73B1553-A13A-4989-B045-A589A8F2B9DC
• 1-(2-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione
• 1-(2-deoxy-beta-delta-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione
• 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-2,4(1H,3H)-Pyrimidinedione
• 1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1H,3H)-Pyrimidinedione
• 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-H-pyrimidine-2,4-dione
• 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7588	75.88%
Caco-2	-	0.9416	94.16%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Nucleus	0.7527	75.27%
OATP2B1 inhibitior	-	0.8665	86.65%
OATP1B1 inhibitior	+	0.9531	95.31%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9796	97.96%
P-glycoprotein inhibitior	-	0.9764	97.64%
P-glycoprotein substrate	-	0.9608	96.08%
CYP3A4 substrate	-	0.5494	54.94%
CYP2C9 substrate	-	0.7659	76.59%
CYP2D6 substrate	-	0.8637	86.37%
CYP3A4 inhibition	-	0.9249	92.49%
CYP2C9 inhibition	-	0.9459	94.59%
CYP2C19 inhibition	-	0.9499	94.99%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9479	94.79%
CYP2C8 inhibition	-	0.9613	96.13%
CYP inhibitory promiscuity	-	0.9490	94.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5043	50.43%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9733	97.33%
Skin irritation	-	0.8558	85.58%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7431	74.31%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	+	0.8423	84.23%
skin sensitisation	-	0.9371	93.71%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.4784	47.84%
Acute Oral Toxicity (c)	IV	0.4315	43.15%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.7229	72.29%
Thyroid receptor binding	+	0.5464	54.64%
Glucocorticoid receptor binding	+	0.7631	76.31%
Aromatase binding	-	0.7513	75.13%
PPAR gamma	+	0.7132	71.32%
Honey bee toxicity	-	0.8949	89.49%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.6410	64.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.63%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.06%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	95.08%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.75%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.19%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.89%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.62%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.54%	85.14%
CHEMBL220	P22303	Acetylcholinesterase	83.43%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	83.12%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.67%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.56%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.28%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.09%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.06%	100.00%

Plants that contains it

• Euryale ferox
• Ginkgo biloba

Cross-Links

• PubChem: 13712
• NPASS: NPC106780
• ChEMBL: CHEMBL353955
• LOTUS: LTS0201959
• wikiData: Q419140