基本情報
- CAS
1867-73-8- 標準SMILES
CNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O- InChIKey
VQAYFKKCNSOZKM-IOSLPCCCSA-N- 分子式
- C11H15N5O4
- 平均分子量
- 281.27 g/mol
- 単同位体質量
- 281.11240396
概要
N(6)-methyladenosine is a methyladenosine compound with one methyl group attached to N6 of the adenine nucleobase.
名称と識別子
- 優先名称
- N6-Methyladenosine
- IUPAC
- (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolane-3,4-diol
- 現地名
- N-メチルアデノシン
- 英語名
- 6-Methylaminopurine 9-ribofuranoside
- 分子式
- C11H15N5O4
- 分子量
- 281.27
名称と別名
N6-Methyladenosine1867-73-8N-Methyladenosine6-MethyladenosineN(6)-Methyladenosine6-Methylaminopurinosine6-Methylaminopurine riboside6-Methylaminopurine D-ribosideN6-methyladenosine (m6A)6-Methylaminopurine ribonucleosideCHEBI:21891CLE6G00625
名称をさらに表示
6-メチルアミノプリンリボシドN6-メチルアデノシンN-メチルアデノシンメチル-6-アデノシン(2R,3S,4R,5R)-2-(ヒドロキシメチル)-5-[6-(メチルアミノ)-9H-プリン-9-イル]オキソラン-3,4-ジオールCS-1297N6-Me-AN6-Me-rAN6-Me-ArN6-Me-AdenosineN6,N6-Methyladenosin
NSC-29409DTXSID6020858(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]oxolane-3,4-diolN(6)mAdo(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(methylamino)-9H-purin-9-yl)oxolane-3,4-diolRefChem:927418DTXCID20858Adenosine, N-methyl-
データベース識別子
- CAS
1867-73-8- PubChem CID
- 102175
- DTXSID
DTXSID6020858- ChEMBL
CHEMBL383144- ChEBI
CHEBI:21891- UNII
- CLE6G00625
- Nikkaji
- J130.669C
物性
構造計算による物性
- XLogP
- -0.4
- 極性表面積
- 126 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 8
- 回転可能結合数
- 3
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 349
実験および物理化学的性質
Physical DescriptionSolid
Collision Cross Section159.67 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
物理化学的性質
- 融点
- 172 °C · 172 °C
- 沸点
- 649.1 · 649.1±65.0 °C(Predicted)
- 比重(密度)
- 1.85 · 1.85±0.1 g/cm3(Predicted)
- 貯蔵温度
- 2 · Keep in dark place,Sealed in dry,2-8°C
- 溶解性
- DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
- 酸解離定数(Pka)
- 13.12 · 13.12±0.70(Predicted)
- 外見
- Powder
- 色
- White to off-white
- PH
- 4 · 4.0
- 安定性
- 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
化学と産業
薬理情報
MeSH Pharmacological Classification
Substances that are destructive to protozoans.
Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Tissue LocationsPlacenta
応用分野
説明N6-Methyladenosine is an adenosine analog. 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. It also inhibits tumor growth in the C3H/ST and C3HB/ST mouse models of spontaneous mammary adenocarcinomas. N6-Methyladenosine is also the most prevelant mRNA modification in eukaryotes and has roles in cell viability and development.
使用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.
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補足説明
定義ChEBI: A methyladenosine compound with one methyl group attached to N6 of the adenine nucleobase.
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