5-Bromouracil - ≥99% , CAS No.51-20-7

CAS: 51-20-7 Cat. No.: B109680 Molecular Weight: 190.98 Beilstein Registry Number: 127176 EC Number: 200-084-0

GRADE & PURITY ≥99%

Synonyms

Q238477 | Z275128628 | AB00570 | SR-01000636400-1 | 4HK400G5UO | InChI=1/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9 | 5-Bromouracil | 5-bromo-uracil | AC-3034 | AM83917 | B-9200 | F3096-1702 | 5-Bromouracil, 98% | BP-12090 | 5-BrU | Bromhydroxypyrimi

Storage

Room temperature

Shipped In

Normal

Overview

application：

A major chemical mutagen. Incorporates into DNA, altering base-pair sequencing by replacing thymine.

Specifications

Synonyms

Q238477 | Z275128628 | AB00570 | SR-01000636400-1 | 4HK400G5UO | InChI=1/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H, (H2, 6, 7, 8, 9 | 5-Bromouracil | 5-bromo-uracil | AC-3034 | AM83917 | B-9200 | F3096-1702 | 5-Bromouracil, 98% | BP-12090 | 5-BrU | Bromhydroxypyrimi

Specifications & Purity

≥99%

Storage

Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488179941
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179941
• Canonical Smiles: C1=C(C(=O)NC(=O)N1)Br
• IUPAC Name: 5-bromo-1H-pyrimidine-2,4-dione
• InChIKey: LQLQRFGHAALLLE-UHFFFAOYSA-N
• INCHI: 1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1)Br
• WGK Germany: 3
• RTECS: YQ9060000
• UN Number: 2811
• Packing Group: I
• Molecular Weight: 190.98
• Beilstein: 127176
• Reaxy-Rn: 127176
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=127176&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Halopyrimidines
• Alternative Parents: Hydroxypyrimidines Aryl bromides Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Hydroxypyrimidine - Halopyrimidine - Aryl halide - Aryl bromide - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organobromide - Organohalogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
• External Descriptors: pyrimidines - nucleobase analogue

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

Associated Targets(Human)

Raji (5516 Activities)

Explore this target

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

Associated Targets(non-human)

L1210 (27553 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO (Slightly), Water (Slightly)
• Melt Point(°C): >300 °C
• Molecular Weight: 190.980 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 189.938 Da
• Monoisotopic Mass: 189.938 Da
• Topological Polar Surface Area: 58.200 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 199.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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

References

1. Hanwen Liu, Ying Liu, Ting Zhou, Penghui Zhou, Jianguo Li, Anping Deng.  (2022)  Ultrasensitive and Specific Detection of Anticancer Drug 5-Fluorouracil in Blood Samples by a Surface-Enhanced Raman Scattering (SERS)-Based Lateral Flow Immunochromatographic Assay.  MOLECULES,  27  (13): (4019).  [PMID:35807264] [10.3390/molecules27134019]

2. Ting Zhou, Guangzhao He, Changjia Hu, Kang Wu, Ying Liu, Jianguo Li, Anping Deng.  (2022)  Development of a highly sensitive and specific monoclonal antibody-based ELISA coupled with immuno-affinity extraction for the detection of anticancer drug 5-fluorouracil in blood samples.  TALANTA,      [PMID:35696979] [10.1016/j.talanta.2022.123655]

3. Su Xue-ling, Wang Shu-hui, Komal Sumra, Cui Liu-gen, Ni Rui-cong, Zhang Li-rong, Han Sheng-na.  (2022)  The caspase-1 inhibitor VX765 upregulates connexin 43 expression and improves cell–cell communication after myocardial infarction via suppressing the IL-1β/p38 MAPK pathway.  ACTA PHARMACOLOGICA SINICA,  43  (9): (2289-2301).  [PMID:35132192] [10.1038/s41401-021-00845-8]

4. Xiu Liu, Ling Zhang, Jin-Guo Tan, Han-Hong Xu.  (2013)  Design and synthesis of N-alkyl-N′-substituted 2,4-dioxo-3,4-dihydropyrimidin-1-diacylhydrazine derivatives as ecdysone receptor agonist.  BIOORGANIC & MEDICINAL CHEMISTRY,      [PMID:23757207] [10.1016/j.bmc.2013.05.010]

5. Liu-Gen Cui, Miao-Miao Zhai, Jian-Jian Yin, Zhi-Mo Wang, Shu-Hui Wang, Yue-Jiao Zhou, Pei-Pei Li, Yang Wang, Li Xia, Pei Wang, Xue-Xiang Cha, Li-Rong Zhang, Sheng-Na Han.  (2024)  Targeting the ALKBH5-NLRP3 positive feedback loop alleviates cardiomyocyte pyroptosis after myocardial infarction.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:39746531] [10.1016/j.ejphar.2024.177247]