2-フルオロアデノシン

2-Fluoroadenosine

HCID 8975

ノート反応

部分構造検索類似構造を探す

基本情報

CAS: 146-78-1
標準SMILES: Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChIKey: HBUBKKRHXORPQB-UUOKFMHZSA-N
分子式: C10H12FN5O4
平均分子量: 285.23 g/mol
単同位体質量: 285.08733208

概要

2-fluoroadenosine is a member of adenosines and an organofluorine compound.

名称と識別子

優先名称: 2-Fluoroadenosine
IUPAC: (2R,3R,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
現地名: 2-フルオロアデノシン
英語名: 2-Fluoroadenosine
分子式: C10H12FN5O4
分子量: 285.23

名称と別名

2-Fluoroadenosine146-78-1ADENOSINE, 2-FLUORO-6-Amino-2-fluoro-9-beta-D-ribofuranosylpurinePurine, 6-amino-2-fluoro-9-beta-D-ribofuranosyl-0S67290CRJCHEBI:39740DTXSID70163252NSC-30605RefChem:87139DTXCID0085743633-923-8

名称をさらに表示

2-フルオロアデノシン2-フルオロ-9-β-D-リボフラノシル-9H-プリン-6-アミン6-アミノ-2-フルオロ-9-(β-D-リボフラノシル)プリン(2R,3R,4S,5R)-2-(6-アミノ-2-フルオロ-9H-プリン-9-イル)-5-(ヒドロキシメチル)オキソラン-3,4-ジオールnsc306052-Fluorodenosine2-fluoro-adenosin2-Fluoroadenosine>2-Fluoroadenosine USP/EP/BP2-Fluoroadenosine, 10 mM in DMSO

(2R,3R,4S,5R)-2-(6-Amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diolMFCD008663942-(6-AMINO-2-FLUORO-PURIN-9-YL)-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-3,4-DIOL2-Far2-Fas(2R,3R,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diolCHEMBL290077SRI 727

データベース識別子

CAS: 146-78-1
PubChem CID: 8975
DTXSID: DTXSID70163252
ChEMBL: CHEMBL290077
ChEBI: CHEBI:39740
UNII: 0S67290CRJ
EC Number: 633-923-8
Nikkaji: J73.405E

物性

構造計算による物性

XLogP: -0.6
極性表面積: 140 Å²
水素結合供与体数: 4
水素結合受容体数: 9
回転可能結合数: 2
重原子数: 20
形式電荷: 0
複雑度: 367

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

LogP-0.8

Solubility>42.8 [ug/mL] (The mean of the results at pH 7.4)

物理化学的性質

融点: 240 °C · 240 °C (D)(lit.)
沸点: 747.3 · 747.3±70.0 °C(Predicted)
比重(密度): 2.17 · 2.17±0.1 g/cm3(Predicted)
屈折率: -72 ° · -72 ° (C=0.1, EtOH)
貯蔵温度: Keep in dark place,Sealed in dry,Room Temperature
溶解性: DMSO（わずかに、超音波処理）、メタノール（わずかに、加熱、超音波処理）
外見: 個体
酸解離定数(Pka): 13.05 · 13.05±0.70(Predicted)
色: オフホワイト
InChI: InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1
InChIKey: HBUBKKRHXORPQB-UUOKFMHZSA-N
SMILES: OC[C@H]1O[C@@H](N2C3C(=C(N=C(F)N=3)N)N=C2)[C@H](O)[C@@H]1O
CAS データベース: 146 · 146-78-1(CAS DataBase Reference)

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

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

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

wgk: 3
rtecs: AU7386000
毒性: mouse,LD10,unreported,1000ug/kg (1mg/kg),Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.
hs_code: 29349990
risk_code: 22-36/37/38
hazard_code: Xn
safety_code: 26
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 11 - Combustible Solids

化学と産業

応用分野 · 2 件

説明2-Fluoroadenosine (F-Ado) was developed at Southern Research Institute in 1957 as a potential anticancer drug. 2-Fluoroadenosine is not deaminated by adenosine deaminase but metabolized to triphosphate as shown in vitro. The drug was also shown to be a potent inhibitor of lymphocyte-mediated cytolysis.

使用2-Fluoroadenosine is a fluorinated analog of Adenoside nucleotide. It is used as an intermediate for the drug fludarabine. Fludarabine is a purine analogue and antineoplastic agent. It is a chemotherapy medication used in the treatment of leukemia and lymphoma.