6-(benzyloxy)-9H-purin-2-amine

• ChemBase ID: 69988
• Molecular Formular: C12H11N5O
• Molecular Mass: 241.24864
• Monoisotopic Mass: 241.09636
• SMILES: n1c[nH]c2c1nc(N)nc2OCc1ccccc1
• Canonical SMILES: Nc1nc(OCc2ccccc2)c2c(n1)nc[nH]2
• InChI: InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)
• InChIKey: KRWMERLEINMZFT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(benzyloxy)-9H-purin-2-amine; 6-(benzyloxy)-7H-purin-2-amine
• IUPAC Traditional name: 6-(benzyloxy)-9H-purin-2-amine; 6-(benzyloxy)-7H-purin-2-amine
• Synonyms: 6-(Benzyloxy)-7H-purin-2-amine; 6-(Phenylmethoxy)-9H-purin-2-amine; 2-Amino-6-(benzyloxy)purine; NSC 637037; O6-Benzylguanine; 6-(Benzyloxy)-9H-purin-2-amine; O(6)-Benzylguanine; 6-(Benzyloxy)guanine; 6-O-Benzylguanine; O(6)-bGua; O6-BG; O6-Benzylguanine

Database IDs

• CAS Number: 19916-73-5
• MDL Number: MFCD00269931
• PubChem SID: 162035713; 24278259
• PubChem CID: 4578
• Chemspider ID: 4417
• Wikipedia Title: O6-Benzylguanine

CALCULATED PROPERTIES

• Acid pKa: 10.196849
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6720533
• LogD (pH = 7.4): 1.6714947
• Log P: 1.6721176
• Molar Refractivity: 69.2413 cm^3
• Polarizability: 25.45866 Å^3
• Polar Surface Area: 89.71 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Alkali; methanol: soluble20 mg/mL
• Apperance: Light Yellow Solid; solid
• Melting Point: >193°C (dec.); 193(dec.)°C
• Density: 1.432 g/mL

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• 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

Pharmacology Properties

• Gene Information: human ... MGMT(4255)

Product Information

• Purity: ≥98% (TLC); 95+%

DETAILS

Apollo Scientific Ltd - OR7851T

An effective substrate & efficient inactivator of DNA alkyl transferase. Protects against carcinogenic & therapeutic alkylating agents.

Sigma Aldrich - B2292

Biochem/physiol Actions
O(6)-benzylguanine is an antineoplastic agent that binds the DNA repair enzyme O(6)-alkylguanine DNA alkyltransferase (AGT), resulting in inhibition of AGT-mediated DNA repair. It is widely used in various DNA repair mechanism studies and potentiates the effects of other chemotherapeutic agents that damage DNA.

Toronto Research Chemicals - B278500

An irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents.

REFERENCES

• Dolan, M.E., et al.: Proc. Natl. Acad. Sci. USA, 87, 5356 (1990)
• Goodtzova, K., et al.: Biochemistry, 33, 385 (1990)
• Elder, R.H., et al.: Biochem. J., 298, 231 (1994)