| Identification | Back Directory | [Name]
6-METHYLAMINOPURINE 9-RIBOFURANOSIDE | [CAS]
1867-73-8 | [Synonyms]
CS-1297
N6-Me-A
N6-Me-rA
NSC-29409
N-Methyladenosine
Adenosine, N-methyl-
Adenosine Impurity 15
6-Methylaminopurinosine
N6-methyladenosine (m6A)
6-Methylaminopurine D-riboside
6-Methylaminopurine ribonucleoside
6-METHYLAMINOPURINE 9-RIBOFURANOSIDE
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-methylaminopurin-9-yl)oxolane-3,4-diol
(2R,3S,4R,5R)-2-(HydroxyMethyl)-5-(6-(MethylaMino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol | [EINECS(EC#)]
200-001-2 | [Molecular Formula]
C11H15N5O4 | [MDL Number]
MFCD00005739 | [MOL File]
1867-73-8.mol | [Molecular Weight]
281.27 |
| Chemical Properties | Back Directory | [Melting point ]
172 °C | [Boiling point ]
649.1±65.0 °C(Predicted) | [density ]
1.85±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly, Heated, Sonicated) | [form ]
Powder | [pka]
13.12±0.70(Predicted) | [color ]
White to off-white | [PH]
4.0 | [λmax]
262 (pH 1)；266 (pH 7) | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C11H15N5O4/c1-12-9-6-10(14-3-13-9)16(4-15-6)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11,17-19H,2H2,1H3,(H,12,13,14)/t5-,7-,8-,11-/m1/s1 | [InChIKey]
VQAYFKKCNSOZKM-IOSLPCCCSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)NC)N=C2)[C@H](O)[C@@H]1O |
| Hazard Information | Back Directory | [Description]
N6-Methyladenosine is an adenosine analog.1 It inhibits epinephrine-induced contraction of isolated guinea pig ileum and thoracic aorta when used at a concentration of 10 μM. N6-Methyladenosine (1 mg/kg, i.v.) decreases arterial blood pressure and renal blood flow and increases peripheral resistance in anesthetized dogs.2 It also inhibits tumor growth in the C3H/ST and C3HB/ST mouse models of spontaneous mammary adenocarcinomas.3 N6-Methyladenosine is also the most prevelant mRNA modification in eukaryotes and has roles in cell viability and development.4 | [Uses]
N6-Methyladenosine is the most common internal modification of eukaryotic mRNA. The result of this modification is specifically recognized mRNA in the cytoplasm which regulates mRNA stability.N6-Methyladenosine is made when a protein complex containin the writer enzyme METTL3 adds a methyl group to adenosine. Two different eraser enzymes ALKBH5 and FTO can remove a methyl group to turn m6A bach into adenosine. | [Definition]
ChEBI: A methyladenosine compound with one methyl group attached to N6 of the adenine nucleobase. | [References]
[1] S.W. LESLIE T. S M J L Borowitz. Adenosine Analogs: Structure-Activity Relationships in Vascular and Intestinal Smooth Muscle[J]. Journal of pharmaceutical sciences, 1973, 62 9: Pages 1449-1452. DOI: 10.1002/jps.2600620911
[2] T BHANALAPH. Effect of adenosine and some of its analogs on renal hemodyamics.[J]. Journal of medicine, 1973, 4 3: 178-188.
[3] LEONELL C. STRONG PH.D. Henry M B S. Comparison of the effect of three nucleosides and a liver emulsion upon the inhibition of cancer in mice[J]. Journal of Surgical Oncology, 1972, 4 3: 248-254. DOI: 10.1002/jso.2930040308
[4] XIAO WANG. N6-methyladenosine-dependent regulation of messenger RNA stability[J]. Nature, 2013, 505 7481: 117-120. DOI: 10.1038/nature12730 |
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