Deoxyadenosine

HCID 13730CAS 16373-93-6

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Grundinformationen

Standard-SMILES: Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1
InChIKey: OLXZPDWKRNYJJZ-RRKCRQDMSA-N
Summenformel: C10H13N5O3
Durchschnittliche Molmasse: 251,24 g/mol
Monoisotopische Masse: 251,10183928

Überblick

2'-deoxyadenosine is a purine 2'-deoxyribonucleoside having adenine as the nucleobase. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a purines 2'-deoxy-D-ribonucleoside and a purine 2'-deoxyribonucleoside.

Namen und Bezeichner

Bevorzugter Name: Deoxyadenosine
IUPAC: (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

Namen und Synonyme

2'-deoxyadenosinedeoxyadenosine958-09-82-DeoxyadenosineDesoxyadenosineAdenyldeoxyribosideADENOSINE, 2'-DEOXY-Adenine deoxyribose(2R,3S,5R)-5-(6-Aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-olCHEBI:17256Adenine deoxy nucleosideP582C98ULC

Weitere Namen anzeigen

DTXSID10883624(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol9H-Purin-6-amine, 9-(2-deoxy-beta-D-ribofuranosyl)-9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine9H-Purin-6-amine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-9-(2-deoxy-beta-D-ribofuranosyl)-9H-purin-6-amineNSC-83258

Datenbank-Bezeichner

CAS: 16373-93-6、40627-14-3、958-09-8
PubChem CID: 13730
DTXSID: DTXSID10883624
ChEMBL: CHEMBL449329
ChEBI: CHEBI:17256
UNII: P582C98ULC
EC Number: 213-488-7、683-408-7
Nikkaji: J80.042B

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -0,5
Polarare Oberfläche (TPSA): 119 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 7
Frei drehbare Bindungen: 2
Schwere Atome: 18
Formalladung: 0
Komplexität: 307

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives

SpringerMaterials PropertiesAngular frequency

LogP · 2 Einträge

-0.55

-0.68

Melting Point189 °C

Physical Description · 2 Einträge

White odorless crystals; [La-Mar-Ka MSDS]

Solid

Collision Cross Section · 6 Einträge

152.3 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

154.6 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

160.57 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

151.59 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

155.3 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

158.2 Å² [M+H]+

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 25% (1 of 4) of reports.

Warning

Gefahrenhinweise

Regulatory InformationAdenosine, 2'-deoxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryIntraperitoneal LD50 (rat) > 800 mg/kg; [RTECS]

Hazard Classes and Categories · 2 Einträge

Skin Irrit. 2 (75%)

Acute Tox. 3 (100%)

Toxikologische Informationen

Health EffectsChronically high levels of deoxyadenosine are associated Adenosine Deaminase Deficiency.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

Tissue LocationsAll Tissues

Cellular LocationsCytoplasm

Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)