2'-Deoxyuridine - 10mM in DMSO , CAS No.951-78-0

CAS: 951-78-0 Cat. No.: D427065 Peso molecular: 228.2 Beilstein Registry Number: 24433 Número EC: 213-455-7

GRADE & PURITY 10mM in DMSO

Synonyms

1-(2-deoxy-beta-D-erythro-pentofuranosyl)uracil | s5505 | MLS001066344 | bmse000320 | SCHEMBL28844 | 1-(2-Deoxy-ss-D-ribofuranosyl)uracil | 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione | CCRIS 2832 | D0060 | 1-[(2R,4S,5R)-4-hy

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

Application：

2'-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.

Specifications

Sinónimos

1-(2-deoxy-beta-D-erythro-pentofuranosyl)uracil | s5505 | MLS001066344 | bmse000320 | SCHEMBL28844 | 1-(2-Deoxy-ss-D-ribofuranosyl)uracil | 1-[(2R, 4S, 5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2, 4-dione | CCRIS 2832 | D0060 | 1-[(2R, 4S, 5R)-4-hy

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Pyrimidine 2'-deoxyribonucleoside. Frequently halogenated to create thymidine analogs useful for studies of DNA synthesis and degradation mechanisms

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Nombres e identificadores

• Sonrisas canónicas: C1C(C(OC1N2C=CC(=O)NC2=O)CO)O
• IUPAC Name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• InChIKey: MXHRCPNRJAMMIM-SHYZEUOFSA-N
• 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
• Isómeros SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O
• WGK Alemania: 3
• RTECS: YU7490000
• Peso molecular: 228.2
• Beilstein: 24433
• Reaxy-Rn: 18116557
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=18116557&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Clase Pyrimidine nucleosides
      • Subclass Pyrimidine 2'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Clase: Pyrimidine nucleosides
• Subclass: Pyrimidine 2'-deoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidine 2'-deoxyribonucleosides
• Alternative Parents: Pyrimidones Hydropyrimidines Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Ureas Secondary alcohols Lactams Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine 2'-deoxyribonucleoside - Pyrimidone - Hydropyrimidine - Pyrimidine - Heteroaromatic compound - Tetrahydrofuran - Vinylogous amide - Lactam - Secondary alcohol - Urea - Oxacycle - Azacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Alcohol - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
• External Descriptors: Deoxyribonucleosides

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOB Tclin Monoamine oxidase B (8835 Activities)

Discover Target: MAOB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DCK Tchem Deoxycytidine kinase (530 Activities)

Discover Target: DCK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TK1 Tchem Thymidine kinase, cytosolic (627 Activities)

Discover Target: TK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

POLB Tchem DNA polymerase beta (23632 Activities)

Discover Target: POLB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A2780 (11979 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HeLa (62764 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

TK Thymidine kinase (276 Activities)

Discover Target: TK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

deoA Thymidine phosphorylase (531 Activities)

Discover Target: deoA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cdc25b Dual specificity phosphatase Cdc25B (32 Activities)

Discover Target: Cdc25b

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Tk2 Thymidine kinase 2 (53 Activities)

Discover Target: Tk2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Enterococcus faecium (13803 Activities)

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Mus musculus (284745 Activities)

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Hepatitis B virus (7925 Activities)

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Vero (26788 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Air Sensitive
• Rotación específica [α]: 52 ° (C=1, 1mol/L NaOH)
• Punto de fusión (°C): 160-168°C
• Peso molecular: 228.200 g/mol
• XLogP3: -1.600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 228.075 Da
• Monoisotopic Mass: 228.075 Da
• Topological Polar Surface Area: 99.100 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 343.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Qiuhua Zhang, Lingyi Huang, Youjia Wu, Liying Huang, Xiaowen Xu, Renyi Lin.  (2022)  Study on Quality Control of Compound Anoectochilus roxburghii (Wall.) Lindl. by Liquid Chromatography–Tandem Mass Spectrometry.  MOLECULES,  27  (13): (4130).  [PMID:35807378] [10.3390/molecules27134130]

2. Gaofei Liu, Xin Tong, Jialing Wang, Bin Wu, Jianlin Chu, Yongchan Jian, Bingfang He.  (2021)  Reshaping the binding pocket of purine nucleoside phosphorylase for improved production of 2-halogenated-2′-deoxyadenosines.  Catalysis Science & Technology,  11  (13): (4439-4446).  [PMID:] [10.1039/D0CY02424D]

3. Wang Xue-Jie, You Jin-Zong.  (2015)  Study on the molecular structure and thermal stability of pyrimidine nucleoside analogs.  JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY,  120  (1): (1009-1025).  [PMID:] [10.1007/s10973-014-4362-6]

4. Mengzhen Jiang, Ruohan Xu, Chunyan Yang, Haili Wang, Jinyuan Cai, Yanrong Wen, Mingfu Ye, Tingxuan Yan, Shuangshou Wang.  (2025)  Boronate affinity-mediated multi-mode visual sensing of cis-diol compounds in both biological and food samples.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2025.137335]

5. Liyue Hou, Zhen Zhang, Siqi Li, Ligai Bai.  (2025)  Specific extraction of S-adenosylhomocysteine from urine with boronate affinity mechanism based on a tube-tip adsorbent.  ANALYTICA CHIMICA ACTA,      [PMID:40057311] [10.1016/j.aca.2025.343811]

6. Yating Li, Jason Tan, Yanqin Tu, Jingnan Wu, Zaifang Zhang, Yifeng Wei, Xinan Jiao, Yan Zhou.  (2025)  Distinct Phage-Encoded Enzymes for Substitution of Deoxythymidine by Deoxyuridine in Phage Genomes.  Advanced Science,      [PMID:41001765] [10.1002/advs.202512937]

7. Dan-Qian Chen, Gang Cao, Hua Chen, Dan Liu, Wei Su, Xiao-Yong Yu, Nosratola D. Vaziri, Xiu-Hua Liu, Xu Bai, Li Zhang, Ying-Yong Zhao.  (2017)  Gene and protein expressions and metabolomics exhibit activated redox signaling and wnt/β-catenin pathway are associated with metabolite dysfunction in patients with chronic kidney disease.  Redox Biology,      [PMID:28343144] [10.1016/j.redox.2017.03.017]

8. Li Hengye, Zhang Xuemeng, Zhang Lin, Cang Hui, Kong Fenying, Fan Dahe, Wang Wei.  (2018)  Hyperbranched Polyglycerol Functionalized Silica Stationary Phase for Hydrophilic Interaction Liquid Chromatography.  ANALYTICAL SCIENCES,  34  (4): (433-438).  [PMID:29643306] [10.2116/analsci.17P486]

9. Zhipeng Zhu, Yuqian Xiang, Xiaohui Yan, Chenglong Shi, Cheng Chen, Hongxing Liu, Bin Wang, Yanshuo Li, Dapeng Wu.  (2025)  Stable cross-linked polyacrylamide stationary phase based on atom transfer radical polymerization for hydrophilic interaction liquid chromatography.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.113818]