sodium (4aR,6R,7R,7aR)-6-{6-amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate hydrate

• ChemBase ID: 153768
• Molecular Formular: C17H18ClN5NaO7PS
• Molecular Mass: 525.835651
• Monoisotopic Mass: 525.02507753
• SMILES: CO[C@@H]1[C@H]2[C@@H](COP(=O)(O2)[O-])O[C@H]1n1c2c(c(ncn2)N)nc1Sc1ccc(cc1)Cl.O.[Na+]
• Canonical SMILES: CO[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(Sc2ccc(cc2)Cl)nc2c1ncnc2N.O.[Na+]
• InChI: InChI=1S/C17H17ClN5O6PS.Na.H2O/c1-26-13-12-10(6-27-30(24,25)29-12)28-16(13)23-15-11(14(19)20-7-21-15)22-17(23)31-9-4-2-8(18)3-5-9;;/h2-5,7,10,12-13,16H,6H2,1H3,(H,24,25)(H2,19,20,21);;1H2/q;+1;/p-1/t10-,12-,13-,16-;;/m1../s1
• InChIKey: NVPSOXGMFVFZIS-IPBMGFFTSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aR)-6-{6-amino-8-[(4-chlorophenyl)sulfanyl]-9H-purin-9-yl}-7-methoxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate hydrate
• IUPAC Traditional name: sodium (4aR,6R,7R,7aR)-6-{6-amino-8-[(4-chlorophenyl)sulfanyl]purin-9-yl}-7-methoxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate hydrate
• Synonyms: 8-pCPT-2′-O-Me-cAMP; 8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic monophosphate monosodium hydrate

Database IDs

• CAS Number: 634207-53-7(anhydrous)
• MDL Number: MFCD11045952
• PubChem SID: 162247907; 24893122
• PubChem CID: 23679067

CALCULATED PROPERTIES

• Acid pKa: 1.8321451
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 0.38351917
• LogD (pH = 7.4): 0.42517522
• Log P: 0.1781197
• Molar Refractivity: 110.8812 cm^3
• Polarizability: 44.094173 Å^3
• Polar Surface Area: 146.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: white
• Melting Point: 235.5-237.5 °C(lit.)

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H16N5O6ClPSNa · xH2O

DETAILS

Sigma Aldrich - C8988

Biochem/physiol Actions
Analog of natural cAMP, potent and specific membrane-permeant activator of exchange factors directly activated by cAMP (Epac or cAMP-GEF), a new receptor for cyclic AMP