Basic information
- CAS
19916-73-5- Standard SMILES
Nc1nc(OCc2ccccc2)c2[nH]cnc2n1- InChIKey
KRWMERLEINMZFT-UHFFFAOYSA-N- Molecular formula
- C12H11N5O
- Average molar mass
- 241.25 g/mol
- Monoisotopic mass
- 241.09635997
Overview
6-O-benzylguanine has been used in trials studying the treatment of HIV Infection, Adult Gliosarcoma, Adult Glioblastoma, Stage I Adult Hodgkin Lymphoma, and Stage II Adult Hodgkin Lymphoma, among others.
Names & identifiers
- Preferred name
- 6-(Phenylmethoxy)-9H-purin-2-amine
- IUPAC
- 6-phenylmethoxy-7H-purin-2-amine
- English name
- 6-O-Benzylguanine
- Molecular formula
- C12H11N5O
- Molecular weight
- 241.25
Names & synonyms
o6-benzylguanine19916-73-56-O-BenzylguanineO(6)-Benzylguanine2-Amino-6-(benzyloxy)purineO(6)-Bgua2-Amino-6-(phenylmethoxy)-9H-purine6-(Phenylmethoxy)-9H-purin-2-amineNSC-63703701KC87F8FEDTXSID20173700RefChem:854998
Show more names
6-benzylguanineO6-Benzylguanine ,98%O6-BenzyLNSC 6370376-BENZYLOXY GUANINE6-oxo -benzylguanine4 6-Benzyloxyguanine
DTXCID5096191633-744-56-(Benzyloxy)-7H-purin-2-amine6-(benzyloxy)-9H-purin-2-amine2-amino-6-benzyloxypurine6-Benzyloxyguanine6-phenylmethoxy-7H-purin-2-amineKRX-0402
Database identifiers
- CAS
19916-73-5- PubChem CID
- 4578
- DTXSID
DTXSID20173700- ChEMBL
CHEMBL407874- UNII
- 01KC87F8FE
- EC Number
- 449-870-7、633-744-5
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 89.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 271
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility35.9 [ug/mL] (The mean of the results at pH 7.4)
Physicochemical properties
- Melting point
- 193 · 193(dec.)
- Boiling point
- 459.3 · 459.3±55.0 °C(Predicted)
- Density
- 1.48 · 1.48±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- solubility
- 20 mg/mL · methanol: 20 mg/mL
- form
- solid
- pka
- 7.47 · 7.47±0.20(Predicted)
- color
- Off-White to Light Yellow
- 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
- SMILES
- N1C2C(=NC(N)=NC=2OCC2=CC=CC=C2)NC=1
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (97.6%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, 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 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: 6-(Phenylmethoxy)-1H-purin-2-amine (EC: 449-870-7)
Hazard Classes and CategoriesSkin Irrit. 2 (97.6%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Inactive
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications
UsesAn irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents.
UsesO6-Benzylguanine is an effective substrate and efficient inactivator of DNA alkyltransferase. O6-Benzylguanine is an inhibitor of MGMT. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.
Upstream & downstream products
Upstream raw materials
Related reactions
12 records
Compound notes
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