(2R,3R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 126708
• Molecular Formular: C10H13N5O3
• Molecular Mass: 251.24192
• Monoisotopic Mass: 251.1018393
• SMILES: O[C@@H]1C[C@@H](CO)O[C@H]1n1c2ncnc(N)c2nc1
• Canonical SMILES: OC[C@@H]1C[C@H]([C@@H](O1)n1cnc2c1ncnc2N)O
• InChI: InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
• InChIKey: OFEZSBMBBKLLBJ-BAJZRUMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: cordycepin
• Synonyms: Cordycepine; 3'-Deoxyadenosine; Cordycepin; 3′-Deoxyadenosine; Cordycepin

Database IDs

• CAS Number: 73-03-0; 73-03-3
• EC Number: 200-791-4
• MDL Number: MFCD00037998
• Beilstein Number: 35194
• PubChem SID: 24892611; 162221036
• PubChem CID: 6303
• CHEMBL: 305686
• Chemspider ID: 6064
• Wikipedia Title: Cordycepin

CALCULATED PROPERTIES

• Acid pKa: 13.527495
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.5159566
• LogD (pH = 7.4): -1.4023339
• Log P: -1.4006692
• Molar Refractivity: 62.0985 cm^3
• Polarizability: 23.860285 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 225.5°C; 225-229 °C

Safety Information

• RTECS: AU7358610
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: rat ... Adora1(29290)

Product Information

• Purity: ≥98.0% (HPLC)
• Biological Source: from Cordyceps militaris
• Empirical Formula (Hill Notation): C10H13N5O3

DETAILS

Sigma Aldrich - C3394

Biochem/physiol Actions
Cordycepin is an adenosine analogue that is readily converted to cordycepin 5′-triphosphate; can be used for 3′-end labeling of RNA.

Sigma Aldrich - 30925

Other Notes
Starting material for the synthesis of cordycepin triphosphate, an inhibitor of replicative synthesis1
Biochem/physiol Actions
Cordycepin is an adenosine analogue that is readily converted to cordycepin 5′-triphosphate; can be used for 3′-end labeling of RNA.