CPHPC   Click here for help

GtoPdb Ligand ID: 8256

Synonyms: compound 52 [PMID 14998318] [5] | GSK2315698 | Ro 63-8695 [5]
PDB Ligand
Compound class: Synthetic organic
Comment: CPHPC is reported as a chemical which depletes the glycoprotein serum amyloid P component (SAP) in mice [1] and humans [2]. Intellectual property for the use of CPHPC has been licensed to GlaxoSmithKline who have coded the compound GSK2315698. Structurally, CPHPC is a simplified form of a captopril dimer [5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 115.22
Molecular weight 340.16
XLogP -0.15
No. Lipinski's rules broken 0
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InChI InChI=1S/C16H24N2O6/c19-13(17-9-3-5-11(17)15(21)22)7-1-2-8-14(20)18-10-4-6-12(18)16(23)24/h11-12H,1-10H2,(H,21,22)(H,23,24)/t11-,12-/m1/s1
1. Bodin K, Ellmerich S, Kahan MC, Tennent GA, Loesch A, Gilbertson JA, Hutchinson WL, Mangione PP, Gallimore JR, Millar DJ et al.. (2010)
Antibodies to human serum amyloid P component eliminate visceral amyloid deposits.
Nature, 468 (7320): 93-7. [PMID:20962779]
2. Gillmore JD, Tennent GA, Hutchinson WL, Gallimore JR, Lachmann HJ, Goodman HJ, Offer M, Millar DJ, Petrie A, Hawkins PN et al.. (2010)
Sustained pharmacological depletion of serum amyloid P component in patients with systemic amyloidosis.
Br J Haematol, 148 (5): 760-7. [PMID:20064157]
3. Kolstoe SE, Ridha BH, Bellotti V, Wang N, Robinson CV, Crutch SJ, Keir G, Kukkastenvehmas R, Gallimore JR, Hutchinson WL et al.. (2009)
Molecular dissection of Alzheimer's disease neuropathology by depletion of serum amyloid P component.
Proc Natl Acad Sci USA, 106 (18): 7619-23. [PMID:19372378]
4. Pepys MB, Herbert J, Hutchinson WL, Tennent GA, Lachmann HJ, Gallimore JR, Lovat LB, Bartfai T, Alanine A, Hertel C et al.. (2002)
Targeted pharmacological depletion of serum amyloid P component for treatment of human amyloidosis.
Nature, 417 (6886): 254-9. [PMID:12015594]
5. Wermuth CG. (2004)
Selective optimization of side activities: another way for drug discovery.
J Med Chem, 47 (6): 1303-14. [PMID:14998318]