5-nitropyrimidine-2,4-diamine

• ChemBase ID: 104895
• Molecular Formular: C4H5N5O2
• Molecular Mass: 155.1148
• Monoisotopic Mass: 155.04432443
• SMILES: Nc1ncc(c(N)n1)[N+](=O)[O-]
• Canonical SMILES: Nc1ncc(c(n1)N)[N+](=O)[O-]
• InChI: InChI=1S/C4H5N5O2/c5-3-2(9(10)11)1-7-4(6)8-3/h1H,(H4,5,6,7,8)
• InChIKey: UUWYIIVPLIJDMQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-nitropyrimidine-2,4-diamine
• IUPAC Traditional name: 5-nitropyrimidine-2,4-diamine
• Synonyms: 5-Nitro-2,4-pyrimidinediamine; 2,4-Diamino-5-nitro-pyrimidine; NSC 122004; 2,4-DIAMINO-5-NITROPYRIMIDINE; 2,4-Diamino-5-nitropyrimidine

Database IDs

• CAS Number: 18620-73-0
• PubChem SID: 162092196
• PubChem CID: 275293

CALCULATED PROPERTIES

• Acid pKa: 15.100975
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.25076407
• LogD (pH = 7.4): 0.25505626
• Log P: 0.25511128
• Molar Refractivity: 39.7073 cm^3
• Polarizability: 12.901651 Å^3
• Polar Surface Area: 123.64 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot 2N Hydrochloric Acid; Hot Methanol
• Apperance: Fine Yellow Solid; yellow crystalline
• Melting Point: >300°C

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

DETAILS

MP Biomedicals - 02157590

Yellow crystals.

Toronto Research Chemicals - D416500

Has a strong preferential binding to the enzyme dihydrofolate reductase in competition with the substrate, Dihydrofolic Acid.

REFERENCES

• Hitchings, E.A., et al.: J. Biol. Chem., 199, 43 (1952)