CAS 20535-83-5 O-(6)-Methylguanine (HCID 65275)

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Basic information

CAS: 20535-83-5
Standard SMILES: COc1nc(N)nc2nc[nH]c12
InChIKey: BXJHWYVXLGLDMZ-UHFFFAOYSA-N
Molecular formula: C6H7N5O
Average molar mass: 165.15 g/mol
Monoisotopic mass: 165.06505984

Overview

6-O-methylguanine is a methylguanine in which the methyl group is positioned on the oxygen at position 6. Formed in DNA by alkylation of the oxygen atom of guanine, most often by N-nitroso compounds and sometimes due to methylation by other compounds such as endogenous S-adenosylmethionine, it base-pairs to thymine rather than cytidine, causing a G:C to A:T transition in DNA. It has a role as a mutagen.

Names & identifiers

Preferred name: O-(6)-Methylguanine
IUPAC: 6-methoxy-7H-purin-2-amine
English name: 6-O-Methyl-guanine
Molecular formula: C6H7N5O
Molecular weight: 165.15

Names & synonyms

20535-83-56-Methoxyguanine6-O-Methylguanine6-Methoxy-7H-purin-2-amineO6-MethylguanineO-(6)-Methylguanine1H-Purin-2-amine, 6-methoxy-Purine, 2-amino-6-methoxy-6-Methoxy-1H-purine-2-amineO(sup 6)-MethylguanineDTXSID9049405O(6)-methylguanine

Show more names

6-methoxy-9h-purin-2-amineO-METHYLGUANINEo(sup6)-methylguanine6-O-Methylguanine 97%Aminomethoxypurine,97%

NSC 37364NSC-373649B710FV2AEDTXCID8029365CHEBI:20689METHYLGUANINE, O(6)-NELARABINE METABOLITE (METHYLGUANINE)6-methylguanine

Database identifiers

CAS: 20535-83-5
PubChem CID: 65275
DTXSID: DTXSID9049405
ChEMBL: CHEMBL226395
ChEBI: CHEBI:20689
UNII: 9B710FV2AE
EC Number

Properties

Computed structural properties

XLogP: -0.2
Topological polar surface area: 89.7 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 1
Heavy atoms: 12
Formal charge: 0
Complexity: 166

Experimental & physicochemical properties

Solubility>24.8 [ug/mL] (The mean of the results at pH 7.4)

Physicochemical properties

Melting point: 300 °C · >300 °C(lit.)
Boiling point: 598.5 · 598.5±53.0 °C(Predicted)
Density: 1.531 · 1.531±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: DMSO (Slightly, Heated), Water (Slightly, Heated)
form: Solid
pka: 9.74 · 9.74±0.10(Predicted)
color: Off-White to Pale Yellow
BRN: 645384 · 645384
InChI: InChI=1S/C6H7N5O/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)
InChIKey: BXJHWYVXLGLDMZ-UHFFFAOYSA-N
SMILES: N1C2C(=NC(N)=NC=2OC)NC=1

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
rtecs: UO7473000
hs_code: 29349990
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302+H312+H332-H315-H319
Precautionary statements: P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501

Chemistry & industry

Applications · 3 items

UsesAntitumor agent

UsesThese Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards