6-Azuridine (6-Azauridine) is a purine nucleoside analogue. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc.

Purpose

6-Azauridine (AzUrd) blocks the conversion of orotic acid into UMP and it is used in antiviral studies.
6-Azauridine has been used:
in uridine monophosphate synthase (UMPS) activity assay
as an antiviral agent to study its inhibition effect and cytotoxic potential on foot and mouth disease virus
to screen for anticryptosporidial activity
in the pretreatment of HeLa cells to study its effect on inhibition of cellular uridine synthesis before and during chase with 5-bromouridine 5′-triphosphate (BrUTP)
as a reference compound for comparing the antiviral activity and cytotoxic activity against viral host cell lines

Specifications

Sinónimos

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

6-azauridine is a prodrug, upon conversion to 6-aza-UMP, inhibits uridine monophosphate synthase (UMPS). It is a broad spectrum anti-metabolite.It interferes with pyrimidine biosynthesis and affects the cellular nucleic acid levels. It is considered as a

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.

Pureza

≥98%

Nombres e identificadores

Sonrisas canónicas	C1=NN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
IUPAC Name	2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazine-3,5-dione
InChIKey	WYXSYVWAUAUWLD-SHUUEZRQSA-N
INCHI	1S/C8H11N3O6/c12-2-3-5(14)6(15)7(17-3)11-8(16)10-4(13)1-9-11/h1,3,5-7,12,14-15H,2H2,(H,10,13,16)/t3-,5-,6-,7-/m1/s1
Isómeros SMILES	C1=NN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
Peso molecular	245.19
Reaxy-Rn	24730831
Reaxys-RN_link_address	https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24730831&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

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✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Organic oxygen compounds
  - Clase Organooxygen compounds
    - Subclass Carbohydrates and carbohydrate conjugates
      - Level5 Glycosyl compounds
        Level6 Glycosylamines

Kingdom	Organic compounds
Superclass	Organic oxygen compounds
Clase	Organooxygen compounds
Subclass	Carbohydrates and carbohydrate conjugates
Intermediate Tree Nodes	Glycosyl compounds
Direct Parent	Glycosylamines
Alternative Parents	Pentoses 1,2,4-triazines Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Lactams Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
Molecular Framework	Aromatic heteromonocyclic compounds
Substituents	N-glycosyl compound - Pentose monosaccharide - Monosaccharide - Triazine - 1,2,4-triazine - Tetrahydrofuran - Heteroaromatic compound - Secondary alcohol - Lactam - Organoheterocyclic compound - Azacycle - Oxacycle - Hydrocarbon derivative - Alcohol - Primary alcohol - Organic oxide - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
Descripción	This compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
External Descriptors	N-glycosyl-1,2,4-triazine
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

Estructura 3D

Objetivos asociados (humanos)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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CA2 Tclin Carbonic anhydrase II (17698 Activities)

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

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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

HMGCR Tclin HMG-CoA reductase (2475 Activities)

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

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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

INSR Tclin Insulin receptor (5558 Activities)

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

PGR Tclin Progesterone receptor (8562 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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

AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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CALCR Tclin Calcitonin receptor (2215 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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

HRH1 Tclin Histamine H1 receptor (7573 Activities)

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

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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

OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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

SLC6A3 Tclin Dopamine transporter (10535 Activities)

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

KCNH2 Tclin HERG (29587 Activities)

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

HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

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

ESR2 Tclin Estrogen receptor beta (9272 Activities)

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CYSLTR1 Tclin Cysteinyl leukotriene receptor 1 (2118 Activities)

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

ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)

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

CHRM4 Tclin Muscarinic acetylcholine receptor M4 (6041 Activities)

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

CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)

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Objetivos asociados (no humanos)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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

Mc4r Melanocortin receptor 4 (1205 Activities)

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

Ltc4s Leukotriene C4 synthase (1 Activities)

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Sigmar1 Sigma opioid receptor (160 Activities)

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

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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

Cckar Cholecystokinin A receptor (90 Activities)

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Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Human orthopneumovirus (392 Activities)

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Rattus norvegicus (775804 Activities)

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Vaccinia virus (4609 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Coxsackievirus B5 (476 Activities)

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Poliovirus 1 (1274 Activities)

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Reovirus sp. (323 Activities)

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West Nile virus (623 Activities)

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Yellow fever virus (1530 Activities)

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Vesicular stomatitis virus (4460 Activities)

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Dengue virus (413 Activities)

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Respiratory syncytial virus (3434 Activities)

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BHK-21 (725 Activities)

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L1210 (27553 Activities)

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Vero (26788 Activities)

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Bovine viral diarrhea virus 1 (1277 Activities)

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ompdc Orotidine phosphate decarboxylase (9 Activities)

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

pyrF Orotidine 5'-phosphate decarboxylase (39 Activities)

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

dengue virus type 2 (2400 Activities)

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Coxsackievirus B2 (343 Activities)

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Mammalian orthoreovirus 1 (1523 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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

NS1 Nonstructural protein 1 (33327 Activities)

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HSP40, subfamily A, putative (505 Activities)

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SKN7 Transcription factor SKN7 (365 Activities)

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Glra2 Glycine receptor (1745 Activities)

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Vero 76 (245 Activities)

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Chikungunya virus (1339 Activities)

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SARS-CoV-2 (38078 Activities)

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Mecanismos de acción

Certificados (CoA, COO, BSE/TSE y tabla de análisis)

C of A & Other Certificates(BSE/TSE, COO):

Analytical Chart:

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8 results found

Lot Number	Certificate Type	Fecha	Articulo
I2407138	Certificate of Analysis	Aug 02, 2024	A170898
I2407139	Certificate of Analysis	Aug 02, 2024	A170898
I2407145	Certificate of Analysis	Aug 02, 2024	A170898
I2407162	Certificate of Analysis	Aug 02, 2024	A170898
I2407164	Certificate of Analysis	Aug 02, 2024	A170898
I2407167	Certificate of Analysis	Aug 02, 2024	A170898
I2407168	Certificate of Analysis	Aug 02, 2024	A170898
I2407173	Certificate of Analysis	Aug 02, 2024	A170898

Propiedades químicas y físicas

Sensibilidad	Heat Sensitive
Rotación específica [α]	-134° (C=1,Pyridine)
Punto de fusión (°C)	158 °C
Peso molecular	245.190 g/mol
XLogP3	-2.100
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	245.065 Da
Monoisotopic Mass	245.065 Da
Topological Polar Surface Area	132.000 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	372.000
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

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6-Azauridine - ≥98% , CAS No.54-25-1

Why this grade

Storage & shipping

Quality documents

Literature proof

Descripción general

Specifications

Documentation

📋 Safety Data Sheet (SDS)

✅ Certificate of Analysis (COA)

📊 Datasheet

🔬 Specification Sheet

Advanced Data

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