(6S)-1-[(4-amino-3-methylphenyl)methyl]-5-(2,2-diphenylacetyl)-1H,4H,5H,6H,7H-imidazo[4,5-c]pyridine-6-carboxylic acid trifluoroacetic acid hydrate

• ChemBase ID: 154059
• Molecular Formular: C31H31F3N4O6
• Molecular Mass: 612.5962496
• Monoisotopic Mass: 612.21956939
• SMILES: Cc1cc(ccc1N)Cn1cnc2c1C[C@H](N(C2)C(=O)C(c1ccccc1)c1ccccc1)C(=O)O.C(=O)(C(F)(F)F)O.O
• Canonical SMILES: OC(=O)C(F)(F)F.OC(=O)[C@@H]1Cc2c(CN1C(=O)C(c1ccccc1)c1ccccc1)ncn2Cc1ccc(c(c1)C)N.O
• InChI: InChI=1S/C29H28N4O3.C2HF3O2.H2O/c1-19-14-20(12-13-23(19)30)16-32-18-31-24-17-33(26(29(35)36)15-25(24)32)28(34)27(21-8-4-2-5-9-21)22-10-6-3-7-11-22;3-2(4,5)1(6)7;/h2-14,18,26-27H,15-17,30H2,1H3,(H,35,36);(H,6,7);1H2/t26-;;/m0../s1
• InChIKey: IRRZMYRIDIBBQG-ROPHLPQBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-1-[(4-amino-3-methylphenyl)methyl]-5-(2,2-diphenylacetyl)-1H,4H,5H,6H,7H-imidazo[4,5-c]pyridine-6-carboxylic acid trifluoroacetic acid hydrate
• IUPAC Traditional name: (6S)-1-[(4-amino-3-methylphenyl)methyl]-5-(2,2-diphenylacetyl)-4H,6H,7H-imidazo[4,5-c]pyridine-6-carboxylic acid trifluoroacetic acid hydrate
• Synonyms: (S)-1-[(4-Amino-3-methylphenyl)methyl]-5-(diphenylacetyl)-4,5,6,7-tetrahydro-1H-Imidazo[4,5-c]pyridine-6-carboxylic acid trifluoroacetate salt hydrate; S-(+)-PD 123177 trifluoroacetate salt hydrate

Database IDs

• MDL Number: MFCD09265257
• PubChem SID: 24724581; 162248198
• PubChem CID: 71311784

CALCULATED PROPERTIES

• Acid pKa: 3.7144482
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.2711158
• LogD (pH = 7.4): 0.94832814
• Log P: 2.3224716
• Molar Refractivity: 139.0742 cm^3
• Polarizability: 52.61909 Å^3
• Polar Surface Area: 101.45 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: white to off-white solid

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C29H28N4O3 · xC2HF3O2 · yH2O

DETAILS

Sigma Aldrich - P5749

Biochem/physiol Actions
S-(+)-PD 123177 is selective AT2 angiotensin receptor antagonist. The angiotensin AT2 receptor is an atypical seven transmembrane domain receptor that is coupled to activation of tyrosine phosphatase and inhibition of MAP kinase, and does not undergo agonist-induced internalization. An investigation of the occurrence and nature of AT2 receptor phosphorylation revealed that phorbol ester-induced activation of protein kinase C (PKC) in HA-AT2 receptor-expressing COS-7 cells caused rapid and specific phosphorylation of a single residue (Ser354) located in the cytoplasmic tail of the receptor. Agonist activation of AT2 receptors by angiotensin II (Ang II) also caused rapid PKC-dependent phosphorylation of Ser354 that was prevented by the AT2 antagonist, S-(+)-PD 123177, and by inhibitors of PKC. In cells coexpressing AT1 and AT2 receptors, Ang II-induced phosphorylation of the AT2 receptor was reduced by S-(+)-PD 123177 and abolished by treatment with both antagonists or with PKC inhibitors. These findings indicate that the AT2 receptor is rapidly phosphorylated via PKC during homologous activation by Ang II, and also undergoes heterologous PKC-dependent phosphorylation during activation of the AT1 receptor.