sodium (4aR,6R,7R,7aR)-6-(6-butanamido-9H-purin-9-yl)-7-(butanoyloxy)-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

• ChemBase ID: 132431
• Molecular Formular: C18H23N5NaO8P
• Molecular Mass: 491.367451
• Monoisotopic Mass: 491.11819363
• SMILES: CCCC(=O)Nc1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])OC(=O)CCC.[Na+]
• Canonical SMILES: CCCC(=O)O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1cnc2c1ncnc2NC(=O)CCC.[Na+]
• InChI: InChI=1S/C18H24N5O8P.Na/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14;/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);/q;+1/p-1/t10-,14-,15-,18-;/m1./s1
• InChIKey: KRBZRVBLIUDQNG-JBVYASIDSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aR)-6-(6-butanamido-9H-purin-9-yl)-7-(butanoyloxy)-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• IUPAC Traditional name: sodium (4aR,6R,7R,7aR)-6-(6-butanamidopurin-9-yl)-7-(butanoyloxy)-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• Synonyms: N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt; 二丁酰 cAMP 钠盐; 二丁酰环磷腺苷 钠盐; 布拉地新 钠盐; N6,2′-O-二丁酰基腺苷3′,5′-环磷酸 钠盐

Database IDs

• CAS Number: 16980-89-5
• EC Number: 241-059-4
• MDL Number: MFCD00005843
• PubChem SID: 24893221; 162226708; 24893246
• PubChem CID: 23663967

CALCULATED PROPERTIES

• Acid pKa: 1.8274206
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -0.8815789
• LogD (pH = 7.4): -0.89628386
• Log P: -0.48056093
• Molar Refractivity: 106.9377 cm^3
• Polarizability: 42.676678 Å^3
• Polar Surface Area: 166.82 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL; H2O: soluble50 mg/mL
• Apperance: off-white powder; white powder

Safety Information

• RTECS: ES5055500
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (HPLC); ≥97% (HPLC)
• Impurities: ≤0.5% Cyclic AMP; ≤0.5% cyclic AMP and 2′-O-monobutyryl-cyclic AMP; ≤3% monobutyryl derivatives; ≤3% N6-monobutyryl-cyclic AMP

DETAILS

Sigma Aldrich - D0260

Biochem/physiol Actions
细胞通透性 cAMP 类似物，可激活 cAMP 依赖性蛋白激酶 (PKA)。
Caution
Loses 2′-O-butyryl group at pH 8.5

Sigma Aldrich - D0627

Biochem/physiol Actions
细胞通透性 cAMP 类似物，可激活 cAMP 依赖性蛋白激酶 (PKA)。
Caution
在 pH 8.5 下会失去 2′-O-丁酰基
Application
Dibutyryl cAMP is a cell-permeable cAMP analogue that activates cAMP dependent protein kinase (PKA) or the cAMP/PKA signaling pathway. Dibutyryl cAMP is used as a morphological differentiation inducer and cell signaling modulator in cells such as Schwann cells. It is used in a variety of neural differentiation studies.