Basic information
- CAS
461-89-2- Standard SMILES
O=c1cn[nH]c(=O)[nH]1- InChIKey
SSPYSWLZOPCOLO-UHFFFAOYSA-N- Molecular formula
- C3H3N3O2
- Average molar mass
- 113.08 g/mol
- Monoisotopic mass
- 113.02252634
Overview
6-azauracil is a 1,2,4-triazine compound having oxo-substituents at the 3- and 5-positions. It has a role as an antimetabolite. It is a member of 1,2,4-triazines and a nucleobase analogue.
Names & identifiers
- Preferred name
- 1,2,4-Triazine-3,5(2H,4H)-dione
- IUPAC
- 2H-1,2,4-triazine-3,5-dione
- English name
- 6-Azauracil
- Molecular formula
- C3H3N3O2
- Molecular weight
- 113.07
Names & synonyms
6-Azauracil461-89-21,2,4-Triazine-3,5(2H,4H)-dioneAzauracil4(6)-Azauracilas-Triazine-3,5-diolas-Triazine-3,5(2H,4H)-dioneNSC-3425I14TWN70LRDTXSID2060042CHEBI:53745RefChem:104235
Show more names
AZU6-AUhHBPNAZCAZAMPnsc3425ipo3834
DTXCID4040474207-318-02H-1,2,4-triazine-3,5-dione1,2,4-Triazine-3,5-diol18802-37-41,2,4-Triazine-3,5-dioneUSAF CB-30IPO 3834
Database identifiers
- CAS
461-89-2- PubChem CID
- 68037
- DTXSID
DTXSID2060042- ChEMBL
CHEMBL2260276- ChEBI
CHEBI:53745- UNII
- I14TWN70LR
- EC Number
- 207-318-0
- Nikkaji
- J9.363G
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 70.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 162
Experimental & physicochemical properties
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP-1.37
Physicochemical properties
- Melting point
- 274 · 274-275 °C(lit.)
- Boiling point
- 211.75 °C · 211.75°C (rough estimate)
- Density
- 1.5988 · 1.5988 (rough estimate)
- refractive index
- 1.4264 · 1.4264 (estimate)
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 1 M · 1 M NH4OH: 50mg/mL, clear to slightly hazy, colorless to light yellow-green
- pka
- 7.78 · 7.78±0.20(Predicted)
- form
- Fine Crystalline Powder
- color
- White to light yellow
- Water Solubility
- 1 M · Partly soluble in water, ethanol, DMSO, and 1 M NH4OH (50 mg/ml).
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (89.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (89.6%)
Safety data
- F
- 10-23
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- XY7700000
- hs_code
- 29336980
- risk_code
- 36/37/38-63-25
- Signal word
- Warning
- Symbol(GHS)
- GHS06
- hazard_code
- Xi,T
- safety_code
- 26-36-45-38-36/37/39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H301-H315-H319-H335
- Precautionary statements
- P261-P280a-P301+P310a-P305+P351+P338-P405-P501a
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)
Uses & manufacturing
General Manufacturing Information1,2,4-Triazine-3,5(2H,4H)-dione: ACTIVE
Applications
Uses6-Azauracil (6-AU) is used as a growth inhibitor of various microorganisms via depletion of intracellular GTP and UTP nucleotide pools. 6-Azauracil has been widely used in investigations on modulation of transcription, especially in yeast models.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
12 records
Compound notes
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