2'-Fluoro-2'-deoxyadenosine

HCID 100253

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Substructure search Find similar structures

Basic information

CAS: 64183-27-3
Standard SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1F
InChIKey: ZGYYPTJWJBEXBC-QYYRPYCUSA-N
Molecular formula: C10H12FN5O3
Average molar mass: 269.23 g/mol
Monoisotopic mass: 269.09241746

Names & identifiers

Preferred name: 2'-Fluoro-2'-deoxyadenosine
IUPAC: (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
English name: 2'-Fluoro-2'-deoxyadenosine
Molecular formula: C10H12FN5O3
Molecular weight: 269.23

Names & synonyms

2'-Fluoro-2'-deoxyadenosine64183-27-32'-Deoxy-2'-fluoroadenosineRefChem:439648814-045-65'-FDAAdenosine, 2'-deoxy-2'-fluoro-MFCD09750859(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol2'F-dA(2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol2 inverted exclamation marka-Deoxy-2 inverted exclamation marka-fluoroadenosine

Show more names

2''-Fluoro-2''-Deoxyadenosine2'-F-2'-dA2'-Fluoro-2'-dA2′,-F-dAdo2'-F-2'-deoxyadenosine2'-Deoxy-2'-fluoreadenosineAdenosine,2'-deoxy-2'-fluoro-

CHEMBL309579AKOS015900907PD158370(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol9-(2-Deoxy-2-fluoro-beta-D-ribofuranosyl)adenine9-(2-Fluoro-2-deoxy-beta-D-ribofuranosyl)-purin-6-amineSCHEMBL2374042'-F-dA

Database identifiers

CAS: 64183-27-3
PubChem CID: 100253
DTXSID: DTXSID60982712
ChEMBL: CHEMBL309579
EC Number: 814-045-6
Nikkaji: J531.970F

Properties

Computed structural properties

XLogP: 0
Topological polar surface area: 119 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 8
Rotatable bonds: 2
Heavy atoms: 19
Formal charge: 0
Complexity: 338

Physicochemical properties

Melting point: 228 · 228 -231°C
Boiling point: 628.6 · 628.6±65.0 °C(Predicted)
Density: 2.01 · 2.01±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C(protect from light)
solubility: Acetonitrile (Slightly), Methanol (Slightly, Heated)
pka: 12.6 · 12.60±0.70(Predicted)
form: Powder
color: White to Off-white
Water Solubility: Soluble in water.
Stability: Hygroscopic
InChI: InChI=1S/C10H12FN5O3/c11-5-7(18)4(1-17)19-10(5)16-3-15-6-8(12)13-2-14-9(6)16/h2-5,7,10,17-18H,1H2,(H2,12,13,14)/t4-,5-,7-,10-/m1/s1
InChIKey: ZGYYPTJWJBEXBC-QYYRPYCUSA-N
SMILES: OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](F)[C@@H]1O
CAS DataBase Reference: 64183 · 64183-27-3(CAS DataBase Reference)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 319 · H319-H335-H302+H312+H332-H315
Precautionary statements: 271 · P271-P261-P280
HS Code: 2934999090 · 2934999090

Safety & regulation

GHS classification

GHS Classification · 4 items

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)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

hs_code: 2934999090
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H319-H335-H302+H312+H332-H315
Precautionary statements: P271-P261-P280

Chemistry & industry

Applications

Uses2'-Fluoro-2'-deoxyadenosine is a potential prodrug for 2-fluroadenine, involves deoxygenation by reduction of the 2'-thiocar-bonylimidazolide with (Tms)3SiH as hydrogen donor.