Zebularine - Moligand™, ≥98%(HPLC) , CAS No.3690-10-6

CAS: 3690-10-6 Cat. No.: Z135482 Peso molecular: 228.20 PubChem CID: 100016

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

PYRIMIDIN-2-ONE .BETA.-D-RIBOFURANOSIDE | 1-beta-D-Ribofuranosyl-2(1H)-pyrimidino ne | 1-Pentofuranosylpyrimidin-2(1H)-one | 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-Hydroxymethyl-Tetrahydro-Furan-2-yl)-1H-Pyrimidin-2-one | 4pd7 | HMS3677C14 | 4-(Ethoxycarbonyl)c

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

Zebularine is a cell-permeable chemically stable cytidine analog and DNA methylation inhibitor which acts by forming a covalent complex with DNMT. It displays antiangiogenic activity and markedly inhibits vessel formation in different tumor models. It reactivates silenced E-cadherin and potentiates the effects of other epigenetic therapeutics such as vorinistat. Induces differentiation of mesenchymal cells into cardiomyocytes. Inhibits cytidine deaminase (CDD).
An inhibitor of DNA methyltransferase

Specifications

Sinónimos

PYRIMIDIN-2-ONE .BETA.-D-RIBOFURANOSIDE | 1-beta-D-Ribofuranosyl-2(1H)-pyrimidino ne | 1-Pentofuranosylpyrimidin-2(1H)-one | 1-((2R, 3R, 4S, 5R)-3, 4-Dihydroxy-5-Hydroxymethyl-Tetrahydro-Furan-2-yl)-1H-Pyrimidin-2-one | 4pd7 | HMS3677C14 | 4-(Ethoxycarbonyl)c

Especificaciones y pureza

Moligand™, ≥98%(HPLC)

Mecanismos bioquímicos y fisiológicos

Zebularine is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.DNA methyltransferase( DNMT) inhibitor and cytidine deaminase inhibitor (K i = 2 µM). Inhibits tumour growth in vitro and in vivo .

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

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

Grado

Moligand™

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%(HPLC)

Nombres e identificadores

• Pubchem Sid: 504756455
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756455
• Sonrisas canónicas: C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O
• IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• InChIKey: RPQZTTQVRYEKCR-WCTZXXKLSA-N
• INCHI: 1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1
• Isómeros SMILES: C1=CN(C(=O)N=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• PubChem CID: 100016
• Peso molecular: 228.20

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Clase Pyrimidine nucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Clase: Pyrimidine nucleosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidine nucleosides
• Alternative Parents: Glycosylamines Pentoses Pyrimidones Hydropyrimidines Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine nucleoside - Glycosyl compound - N-glycosyl compound - Pentose monosaccharide - Pyrimidone - Hydropyrimidine - Monosaccharide - Pyrimidine - Heteroaromatic compound - Tetrahydrofuran - Secondary alcohol - Azacycle - Oxacycle - Organoheterocyclic compound - Alcohol - Primary alcohol - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as pyrimidine nucleosides. These are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
• External Descriptors: pyrimidine ribonucleosides

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)

ADA Tclin Adenosine deaminase (129 Activities)

Discover Target: ADA

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

CFPAC-1 (421 Activities)

Explore this target

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

T-24 (2342 Activities)

Explore this target

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

HCT-15 (51914 Activities)

Explore this target

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

SIRT6 Tchem NAD-dependent protein deacetylase sirtuin-6 (671 Activities)

Discover Target: SIRT6

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

Objetivos asociados (no humanos)

Cda Cytidine deaminase (37 Activities)

Discover Target: Cda

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

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Mus musculus (284745 Activities)

Explore this target

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

Hepatitis C virus (23859 Activities)

Explore this target

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in DMSO (>25 mg/ml), methanol (5 mg/ml), water (>25 mg/ml), DMF (~5 mg/ml), and ethanol (~0.25 mg/ml).
• Sensibilidad: heat sensitive
• Índice de refracción: 1.7
• Rotación específica [α]: +156.0 ～ +160.0°(C=1, MeOH)
• Punto de ebullición (°C): 499.02° C
• Punto de fusión (°C): 157-160° C
• Peso molecular: 228.200 g/mol
• XLogP3: -1.500
• 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: 103.000 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 343.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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. Liu Xin, Li Jiale, Liu Shuyu, Long Yan, Kang Ching, Zhao Chen, Wei Ling, Huang Shaoqi, Luo Yi, Dai Bo, Zhu Xiangjia.  (2024)  Fabrication of a 3D bioprinting model for posterior capsule opacification using GelMA and PLMA hydrogel-coated resin.  Regenerative Biomaterials,      [PMID:38529352] [10.1093/rb/rbae020]