(2R,3S,4R,5S)-4-amino-2-[6-(dimethylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 133753
• Molecular Formular: C12H18N6O3
• Molecular Mass: 294.30972
• Monoisotopic Mass: 294.14403847
• SMILES: CN(C)c1c2c(ncn1)n(cn2)[C@H]1[C@H]([C@H]([C@H](O1)CO)N)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]([C@H]1N)O)n1cnc2c1ncnc2N(C)C
• InChI: InChI=1S/C12H18N6O3/c1-17(2)10-8-11(15-4-14-10)18(5-16-8)12-9(20)7(13)6(3-19)21-12/h4-7,9,12,19-20H,3,13H2,1-2H3/t6-,7+,9+,12-/m1/s1
• InChIKey: RYSMHWILUNYBFW-VENHTOENSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5S)-4-amino-2-[6-(dimethylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3S,4R,5S)-4-amino-2-[6-(dimethylamino)purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol
• Synonyms: 3′-Amino-3′-deoxy-N6,N6-dimethyladenosine; Puromycin aminonucleoside

Database IDs

• CAS Number: 58-60-6
• EC Number: 200-388-3
• MDL Number: MFCD00063462
• Beilstein Number: 93902
• PubChem SID: 162228030; 24898823
• PubChem CID: 16219893

CALCULATED PROPERTIES

• Acid pKa: 12.978685
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -4.212318
• LogD (pH = 7.4): -2.7506952
• Log P: -1.2608758
• Molar Refractivity: 74.5813 cm^3
• Polarizability: 29.03953 Å^3
• Polar Surface Area: 122.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, slightly yellow

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 48/22
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H373
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target Organ: Kidney

Product Information

• Purity: ≥99.0% (HPLC)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C12H18N6O3

DETAILS

Sigma Aldrich - P7130

Biochem/physiol Actions
Puromycin aminonucleoside is used to study human glomerular disease by inducing damage of murine glomerular podocytes1 and is used to study glomerular function and morphology.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information