5-Hydroxymethyl-2'-deoxyuridine

Category	Herpes simplex Virus (HSV)
CAS	5116-24-5
Description	5-(Hydroxymethyl)-2'-deoxyuridine is a nucleoside analog with anticancer and antiviral activities. It inhibits the replication of murine S180 lung carcinoma cells and Ehrlich ascites mammary carcinoma cells (ED50s = 8.5 and 4 μM, respectively) and multiple human leukemia cell lines (IC50s = 1.7-5.8 μM). 5-(Hydroxymethyl)-2'-deoxyuridine acts synergistically with 5-fluorouracil (5-FU) against HT-29, HCT116, PANC-1, and EKVX cancer cells with no effect on WI38 embryonic lung fibroblasts.

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Synonyms	5-Hydroxymethyl-2'-deoxyuridine;5116-24-5;alpha-Hydroxythymidine;5-Hydroxymethyldeoxyuridine;2'-Deoxy-5-(hydroxymethyl)uridine;HMdU;5-HMdU;alpha-Hydroxy-thymidin;Thymidine, alpha-hydroxy-;CHEBI:61288;Uridine, 2'-deoxy-5-(hydroxymethyl)-;2'-Deoxy-5-hydroxymethyluridine;5-Hydroxymethyl-deoxyuridine;EJZ33W33JN;1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione;MFCD00047489;1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(2-hydroxymethyl)pyrimidine-2,4(1H,3H)-dione;HMdUdr;CCRIS 2347;EINECS 225-848-0;Thymidine, .alpha.-hydroxy-;NSC-749425;5HOMedU;5-Hydroxymethyl-dUrd;5OHMe-dU;Epitope ID:146101;UNII-EJZ33W33JN;SCHEMBL529456;CHEMBL376876;.ALPHA.-HYDROXYTHYMIDINE;DTXSID70965430;2'-Deoxy-5-hydroxymethyl-D-uridine;AKOS016011210;NSC 749425;2'-DESOXY-5-HYDROXYMETHYLURIDINE;AS-60778;PD064172;5-(HYDROXYMETHYL)-2'-DESOXYURIDINE;F82496;A828469;BRD-K45801156-001-01-3;Q27130988;1-(2-Deoxypentofuranosyl)-4-hydroxy-5-(hydroxymethyl)pyrimidin-2(1H)-one;1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(hydroxymethyl)pyrimidine-2,4-dione;
IUPAC Name	1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)pyrimidine-2,4-dione
Molecular Weight	313.34
Molecular Formula	C14H11N5O2S
Canonical SMILES	C1=CC2=NSN=C2C(=C1)NC(=O)N/N=C/C3=CC=C(C=C3)O
InChI	InChI=1S/C10H14N2O6/c13-3-5-2-12(10(17)11-9(5)16)8-1-6(15)7(4-14)18-8/h2,6-8,13-15H,1,3-4H2,(H,11,16,17)/t6-,7+,8+/m0/s1
InChIKey	IPAVKOYJGUMINP-XLPZGREQSA-N
Melting Point	>168°C (dec.)
Purity	≥95%
Density	1.561 g/cm3
Solubility	Soluble in DMSO (Slightly, Sonicated), Methanol (Slightly, Heated), Water (Slightly)
Appearance	Solid
Application	Antineoplastic Agents
Storage	4°C, protect from light *In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)