(2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 133330
• Molecular Formular: C10H12ClN5O4
• Molecular Mass: 301.68638
• Monoisotopic Mass: 301.05778157
• SMILES: c1nc2c(nc(nc2n1[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)Cl)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2N
• InChI: InChI=1S/C10H12ClN5O4/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: BIXYYZIIJIXVFW-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: 2-chloroadenosine
• Synonyms: 2-Chloroadenosine; 2-CADO; 2-Chloroadenosine; 2-氯腺嘌呤核苷; 2-氯腺苷

Database IDs

• CAS Number: 146-77-0
• EC Number: 205-678-3
• MDL Number: MFCD00005734
• Beilstein Number: 43957
• PubChem SID: 162227607; 24277688
• PubChem CID: 8974

CALCULATED PROPERTIES

• Acid pKa: 12.454001
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.1824207
• LogD (pH = 7.4): -1.1824174
• Log P: -1.1824136
• Molar Refractivity: 68.6942 cm^3
• Polarizability: 26.629189 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADORA1(134), ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Product Information

• Purity: 95+%

DETAILS

Sigma Aldrich - C5134

Biochem/physiol Actions
Selective A1 adenosine receptor agonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C5134.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.