2'-Deoxyuridine 5'-monophosphate

Details

• Internal ID: 59a9e4be-8fea-4a49-b787-b3c6cf70a4d1
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine deoxyribonucleotides > Pyrimidine deoxyribonucleoside monophosphates > Pyrimidine 2-deoxyribonucleoside monophosphates
• IUPAC Name: [(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
• SMILES (Canonical): C1C(C(OC1N2C=CC(=O)NC2=O)COP(=O)(O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)COP(=O)(O)O)O
• InChI: InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
• InChI Key: JSRLJPSBLDHEIO-SHYZEUOFSA-N
• Popularity: 977 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃N₂O₈P
• Molecular Weight: 308.18 g/mol
• Exact Mass: 308.04095237 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -3.30
• Atomic LogP (AlogP): -1.71
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• Deoxyuridine monophosphate
• 2'-Deoxyuridine 5'-monophosphate
• 2'-deoxyuridylic acid
• Deoxyuridylic acid
• 2'-deoxy-5'-uridylic acid
• Deoxyuridine 5'-phosphate
• Deoxy-UMP
• 2'-Deoxyuridylate
• 2'-Deoxyuridine 5'-phosphate
• 964-26-1
• Deoxyuridine 5'-monophosphate
• deoxyuridylate
• 5'-Uridylic acid, 2'-deoxy-
• 2'-DEOXYURIDINE-5'-MONOPHOSPHATE
• Uridine, 2'-deoxy-, 5'-(dihydrogen phosphate)
• Uridine, 2'-deoxy-, 5'-phosphate
• CHEMBL211312
• N9J10KFG94
• CHEBI:17622
• EINECS 213-518-9
• BRN 0042143
• 1jmf
• 1jmg
• 1jmi
• 1njb
• 1njd
• 1tsv
• 1tsy
• 1bp0
• 2'-Deoxy-5'-uridylate
• SCHEMBL8200
• 2'-Deoxyuridinemonophosphate
• UNII-N9J10KFG94
• 2''-Deoxyuridinemonophosphate
• 2'-DEOXY-5'-UMP
• 2'-deoxyuridine-5'-phosphate
• 2''-deoxy-5''-uridylic acid
• DTXSID20242223
• BDBM50028108
• BDBM50186267
• DB03800
• [(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
• C00365
• Q2741362
• 2,4(1H,3H)-pyrimidinedione, 1-(2-deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-
• ((2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
• {[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
• 1-{(4S,2R,5R)-4-Hydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1,3-dihydropyrimidine-2,4-dione
• Phosphoric acid mono-[5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6537	65.37%
Caco-2	-	0.8778	87.78%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5984	59.84%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.9520	95.20%
OATP1B3 inhibitior	+	0.9407	94.07%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9891	98.91%
P-glycoprotein inhibitior	-	0.9403	94.03%
P-glycoprotein substrate	-	0.9316	93.16%
CYP3A4 substrate	+	0.5498	54.98%
CYP2C9 substrate	-	0.7709	77.09%
CYP2D6 substrate	-	0.8612	86.12%
CYP3A4 inhibition	-	0.8089	80.89%
CYP2C9 inhibition	-	0.8857	88.57%
CYP2C19 inhibition	-	0.8741	87.41%
CYP2D6 inhibition	-	0.9161	91.61%
CYP1A2 inhibition	-	0.8951	89.51%
CYP2C8 inhibition	-	0.9063	90.63%
CYP inhibitory promiscuity	-	0.9289	92.89%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.4952	49.52%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9692	96.92%
Skin irritation	-	0.7922	79.22%
Skin corrosion	-	0.9343	93.43%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5974	59.74%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	+	0.7746	77.46%
skin sensitisation	-	0.8717	87.17%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6931	69.31%
Acute Oral Toxicity (c)	III	0.5462	54.62%
Estrogen receptor binding	+	0.6645	66.45%
Androgen receptor binding	+	0.7629	76.29%
Thyroid receptor binding	+	0.5439	54.39%
Glucocorticoid receptor binding	+	0.6455	64.55%
Aromatase binding	-	0.5293	52.93%
PPAR gamma	+	0.6249	62.49%
Honey bee toxicity	-	0.8217	82.17%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.7203	72.03%

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	97.76%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.03%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.08%	86.92%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	92.61%	94.01%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.71%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.35%	91.71%
CHEMBL2581	P07339	Cathepsin D	87.14%	98.95%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	87.12%	80.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.10%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.82%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.15%	91.11%
CHEMBL255	P29275	Adenosine A2b receptor	83.77%	98.59%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.52%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.50%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.22%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	82.52%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.00%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.82%	93.04%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 65063
• LOTUS: LTS0149125
• wikiData: Q2741362