N-(9-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-6-yl}-9H-purin-6-yl)butanamide sodium

• ChemBase ID: 134383
• Molecular Formular: C14H18N5NaO7P
• Molecular Mass: 422.285551
• Monoisotopic Mass: 422.08415385
• SMILES: CCCC(=O)Nc1c2c(ncn1)n(cn2)C1C(C2C(O1)COP(=O)(O2)O)O.[Na]
• Canonical SMILES: CCCC(=O)Nc1ncnc2c1ncn2C1OC2C(C1O)OP(=O)(OC2)O.[Na]
• InChI: InChI=1S/C14H18N5O7P.Na/c1-2-3-8(20)18-12-9-13(16-5-15-12)19(6-17-9)14-10(21)11-7(25-14)4-24-27(22,23)26-11;/h5-7,10-11,14,21H,2-4H2,1H3,(H,22,23)(H,15,16,18,20)
• InChIKey: UVMXPHRDUKTUCH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(9-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl}-9H-purin-6-yl)butanamide sodium
• IUPAC Traditional name: N-(9-{2,7-dihydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl}purin-6-yl)butanamide sodium
• Synonyms: 6MB-cAMP; N6-Monobutyryladenosine 3′:5′-cyclic monophosphate sodium salt

Database IDs

• CAS Number: 70253-67-7
• MDL Number: MFCD00057135
• PubChem SID: 24896638; 162228659
• PubChem CID: 16219616

CALCULATED PROPERTIES

• Acid pKa: 1.8277104
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.4677975
• LogD (pH = 7.4): -2.4825165
• Log P: -2.0666783
• Molar Refractivity: 89.68 cm^3
• Polarizability: 35.311317 Å^3
• Polar Surface Area: 157.92 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - M1380

Biochem/physiol Actions
Membrane permeable analog of cAMP that activates protein kinase A and is resistant to degradation by phosphodiesterase