CAS 4546-72-9 N-benzoyl-2'-deoxyadenosine (HCID 107558)

Substructure search Find similar structures

Basic information

CAS: 4546-72-9
Standard SMILES: O=C(Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1)c1ccccc1
InChIKey: PIXHJAPVPCVZSV-YNEHKIRRSA-N
Molecular formula: C17H17N5O4
Average molar mass: 355.3 g/mol
Monoisotopic mass: 355.12805402

Names & identifiers

Preferred name: N-benzoyl-2'-deoxyadenosine
IUPAC: N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
English name: N-Benzoyl-2'-deoxy-adenosine
Molecular formula: C17H17N5O4
Molecular weight: 355.35

Names & synonyms

4546-72-9N-Benzoyl-2'-deoxyadenosineN-BenzoyldeoxyadenosineAdenosine, N-benzoyl-2'-deoxy-EINECS 224-903-6DTXSID80196516RefChem:162888DTXCID20119007224-903-6N6-Benzoyl-2'-deoxyadenosine305808-19-9N-Benzoyl-2'-deoxy-adenosine

Show more names

N-BZ-DA2'-dA(Bz)DA-BZ 99.0%N6-Bz-2'-dAN6-BZ-2'-DEOXYADENOSINEn-benzoyl-2’-deoxy-adenosin

N-(9-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamideN6-Benzoyldeoxyadenosine6-n-benzoyldeoxyadenosineMFCD00009628dA-BzN-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamideN(6)-benzoyl-2'-deoxyadenosineBZ-DEOXYADENOSINE

Database identifiers

CAS: 4546-72-9
PubChem CID: 107558
DTXSID: DTXSID80196516
UNII: 7Y495A66MV
EC Number: 224-903-6
Nikkaji: J297.809A

Properties

Computed structural properties

XLogP: 0.2
Topological polar surface area: 122 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 7
Rotatable bonds: 4
Heavy atoms: 26
Formal charge: 0
Complexity: 504

Experimental & physicochemical properties

LogP0.22

Physicochemical properties

Melting point: 120 · 120-122C
Density: 1.61 · 1.61±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Sealed in dry,Store in freezer, under -20°C
solubility: 30 mg/ml; · DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:6): 0.14 mg/ml; DMSO: 15 mg/ml; Ethanol: 1 mg/ml
form: A crystalline solid
pka: 7.87 · 7.87±0.43(Predicted)
color: White to off-white
Water Solubility: Soluble in water (slightly), and methanol (20 mg/ml).
CAS DataBase Reference: 4546 · 4546-72-9(CAS DataBase Reference)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335

Safety & regulation

Safety data

hs_code: 29349990
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Chemistry & industry

Applications · 2 items

DescriptionN-Benzoyl-2'-deoxyadenosine is a nucleoside analog that is used in the diagnosis of infections caused by bacteria. N-Benzoyl-2'-deoxyadenosine binds to DNA duplexes and alters their structure, which can be detected using electrophoresis. N-Benzoyl-2'-deoxyadenosine has been shown to have low bioavailability and is insoluble in water, so it must be administered intravenously. It has also been found to have anti-inflammatory properties, which may be due to its ability to inhibit prostaglandin synthesis.

UsesReactant in the synthesis of 2', 5'-Dideoxycytidines and Other Derivatives of 2'-Deoxycytidine. Reactant in the synthesis of Mono- and Diamino Analogues of 2-Deoxyadenosine, Cordycepin, 9-(3-Deoxy-α-D-Threo-Pentofuranosyl)-Adenine and 9-(2-Deoxy-α-D-Threo-Pentofuranosyl)Adenine.