CAS 951-78-0 Deoxyuridine (HCID 13712)

Overview

2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is functionally related to a uracil.

Names & identifiers

Preferred name: Deoxyuridine
IUPAC: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
English name: 2'-Deoxyuridine
Molecular formula: C9H12N2O5
Molecular weight: 228.2

Names & synonyms

2'-DEOXYURIDINE951-78-0deoxyuridineUracil deoxyriboside2-DeoxyuridinedURDDeoxyribose uracil2'-DesoxyuridineUridine, 2'-deoxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione1-(2-deoxy-beta-D-erythro-pentofuranosyl)uracilW78I7AY22C

Show more names

DU1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione2'-dUNSC 23615UracildeoxyrDeoxy-uridinDEOXYURIDINE-2'

1-(2-Deoxy-beta-D-erythro-pentofuranoxyl)uracilCHEBI:164502,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-DTXSID308836212,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-erythro-ribofuranosyl)-NSC-236151-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidine-2,4-dione

Database identifiers

CAS: 951-78-0
PubChem CID: 13712
DTXSID: DTXSID30883621
ChEMBL: CHEMBL353955
ChEBI: CHEBI:16450
UNII: W78I7AY22C
EC Number: 213-455-7
Nikkaji: J7.186B

Properties

Computed structural properties

XLogP: -1.6
Topological polar surface area: 99.1 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 16
Formal charge: 0
Complexity: 343

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesCrystal structure

LogP-1.51

Melting Point167 °C

Physical DescriptionSolid

Collision Cross Section · 4 items

145.91 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

151.64 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

156.4 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

157.3 Å² [M+Na]+

Physicochemical properties

Melting point: 167 · 167-169 °C(lit.)
alpha: 22 · D22 +50° (c = 1.1 in N NaOH)
Boiling point: 370.01 °C · 370.01°C (rough estimate)
Density: 1.3705 · 1.3705 (rough estimate)
refractive index: 52 ° · 52 ° (C=1, 1mol/L NaOH)
storage temp.: 2 · Inert atmosphere,2-8°C
solubility: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
form: Powder
pka: 9.3 · pKa 9.3(H2O t = 25) (Uncertain)
color: White to off-white
biological source: synthetic (organic)
Water Solubility: 300 g/L · 300 g/L (20 ºC)
Sensitive: Air Sensitive
Merck: 14 · 14,2910
BRN: 24433 · 24433
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
InChIKey: MXHRCPNRJAMMIM-ATRFCDNQSA-N
SMILES: OC[C@H]1O[C@H](C[C@@H]1O)N2C=CC(=O)NC2=O
CAS DataBase Reference: 951 · 951-78-0(CAS DataBase Reference)
FDA UNII: 78 I7AY22C · W78I7AY22C
EPA Substance Registry System: 2 · Uridine, 2'-deoxy- (951-78-0)
UNSPSC Code: 41116107 · 41116107
NACRES: 51 · NA.51
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xn
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25-37/39-36/37/39-26
WGK Germany: 3 · 3
RTECS: 7490000 · YU7490000
F: 10 · 10-23
Hazard Note: Air Sensitive
TSCA: TSCA listed
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.

Warning

H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (40%)

Safety data

F: 10-23
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
tsca: TSCA listed
rtecs: YU7490000
hs_code: 29349990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
hazard_note: Air Sensitive
safety_code: 22-24/25-37/39-36/37/39-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)

Tissue LocationsBladder

Cellular LocationsExtracellular

Metabolite PathwaysBeta Ureidopropionase Deficiency

Uses & manufacturing

General Manufacturing InformationUridine, 2'-deoxy-: ACTIVE

Applications · 4 items

Description2'-Deoxyuridine is a natural deoxynucleoside, which can be directly used to prepare combined deoxynucleoside drugs or used as chemical reagents for biochemical research. At the same time, it can be used as an intermediate to synthesize some antiviral nucleoside drugs and molecular markers, such as 8-bromo-2-deoxyuridine and 8-hydroxy-2-deoxyuridine from 2'-Deoxyuridine.

Description2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. It has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. It is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.

Uses2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples.

UsesAn uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease

Upstream & downstream products

Downstream products

5-Chloro-2'-deoxyuridine 1-(beta-D-2-Deoxyribofuranosyl)-4-(1,2,4-triazol-1-yl)-5-methylpyrimidin-2-one 5-(2-Hydroxyethyl)-2'-deoxyuridine

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a uracil.