Stercobilin (hydrochloride)

Stercobilin is a fecal pigment and a metabolite of the heme catabolite bilirubin (Cay-17161). It induces DNA damage in a comet assay in HepG2 cells when used at concentrations ranging from 0.5 to 17 µM. Stercobilin (20 and 30 µM) induces activation of NF-kappaB in a reporter assay and increases the expression of the genes encoding TNF-alpha, IL-1beta, IL-6, inducible nitric oxide synthase (iNOS), and COX-2 in RAW 264.7 macrophages. Fecal and plasma levels of stercobilin are increased in ob/ob mice.Formal Name: (2R,3R,4S,16S,17R,18R)-3,18-diethyl-1,2,3,4,5,15,16,17,18,19,22,24-dodecahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid, hydrochloride. CAS Number: 5370-34-3. Synonyms: (-)-Stercobilin, L-Stercobilin. Molecular Formula: C33H46N4O6 . XHCl. Formula Weight: 594.8. Purity: >95% (mixture of isomers). Formulation: (Request formulation change), A solid. Solubility: DMF: soluble, NaOH (aq): soluble. lambdamax: 488 nm. SMILES: OC(CCC1=C(C)C(C[C@@H]2NC([C@H](CC)[C@H]2C)=O)=N/C1=C\C3=C(CCC(O)=O)C(C)=C(C[C@@H]4NC([C@H](C)[C@H]4CC)=O)N3)=O.Cl. InChi Code: InChI=1S/C33H46N4O6.ClH/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26,/h15-16,19-21,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41),1H/b28-15-,/t16-,19-,20-,21-,26+,27+,/m1./s1. InChi Key: WPZBPYPTZWWARY-JRFVQKEISA-N.