(4aR,6R,7R,7aS)-6-{6-amino-8-[(6-aminohexyl)amino]-9H-purin-9-yl}-2,7-dihydroxy-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-one

• ChemBase ID: 133921
• Molecular Formular: C16H26N7O6P
• Molecular Mass: 443.394701
• Monoisotopic Mass: 443.16821822
• SMILES: c1nc(c2c(n1)n(c(n2)NCCCCCCN)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)O)O)N
• Canonical SMILES: NCCCCCCNc1nc2c(n1[C@@H]1O[C@H]3[C@H]([C@H]1O)OP(=O)(OC3)O)ncnc2N
• InChI: InChI=1S/C16H26N7O6P/c17-5-3-1-2-4-6-19-16-22-10-13(18)20-8-21-14(10)23(16)15-11(24)12-9(28-15)7-27-30(25,26)29-12/h8-9,11-12,15,24H,1-7,17H2,(H,19,22)(H,25,26)(H2,18,20,21)/t9-,11-,12-,15-/m1/s1
• InChIKey: WCWLOZYNRVLFOG-SDBHATRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,7aS)-6-{6-amino-8-[(6-aminohexyl)amino]-9H-purin-9-yl}-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• IUPAC Traditional name: (4aR,6R,7R,7aS)-6-{6-amino-8-[(6-aminohexyl)amino]purin-9-yl}-2,7-dihydroxy-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• Synonyms: 8-(6-Aminohexyl)aminoadenosine-3′,5′-cyclic monophosphate; 8-AHA-cAMP; 8-(6-Aminohexyl)aminoadenosine 3′:5′-cyclic monophosphate

Database IDs

• CAS Number: 39824-30-1
• MDL Number: MFCD00057125
• PubChem SID: 24891322; 162228198; 24724386
• PubChem CID: 16078938

CALCULATED PROPERTIES

• Acid pKa: 1.8351647
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.5642824
• LogD (pH = 7.4): -1.5025132
• Log P: -1.5034121
• Molar Refractivity: 106.6184 cm^3
• Polarizability: 41.470924 Å^3
• Polar Surface Area: 192.89 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dilute NaOH: soluble
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; -70°C

Product Information

• Purity: ~98%; ≥98% (HPLC)
• Packaging: vial of 25 μmol
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C16H26N7O6P

DETAILS

Sigma Aldrich - A2104

Biochem/physiol Actions
Selective cAMP-dependent protein kinase (PKA) activator. Site selective cAMP analog with preference for site B of RI of cAMP-dependent protein kinase. In combination with 8-piperidino-cAMP, which selects site A of RI and site B of RII, selective synergistic activation of protein kinase A type I can be obtained.

Sigma Aldrich - A8138

Application
Cyclic AMP analog which shows partially selective agonist activity with Type I cAMP-dependent protein kinase isozyme.1