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MedKoo Cat#: 112034 | Name: Stercobilin HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Stercobilin is a fecal pigment and a metabolite of the heme catabolite bilirubin. 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-κB in a reporter assay and increases the expression of the genes encoding TNF-α, IL-1β, 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.

Chemical Structure

Stercobilin HCl
Stercobilin HCl
CAS#5370-34-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 112034

Name: Stercobilin HCl

CAS#: 5370-34-3 (HCl)

Chemical Formula: C33H47ClN4O6

Exact Mass: 630.3184

Molecular Weight: 631.21

Elemental Analysis: C, 62.79; H, 7.51; Cl, 5.62; N, 8.88; O, 15.21

Price and Availability

Size Price Availability Quantity
1mg USD 400.00 2 Weeks
5mg USD 750.00 2 Weeks
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Related CAS #
34217-90-8 (free) 5370-34-3 (HCl) 635-65-4 (bilirubin)
Synonym
(–)-Stercobilin; L-Stercobilin; (–) Stercobilin; L Stercobilin; Stercobilin; Stercobilin hydrochloride
IUPAC/Chemical Name
3-((Z)-2-((3-(2-carboxyethyl)-5-(((2S,3R,4R)-3-ethyl-4-methyl-5-oxopyrrolidin-2-yl)methyl)-4-methyl-1H-pyrrol-2-yl)methylene)-5-(((2S,3R,4R)-4-ethyl-3-methyl-5-oxopyrrolidin-2-yl)methyl)-4-methyl-2H-pyrrol-3-yl)propanoic acid hydrochloride
InChi Key
WPZBPYPTZWWARY-JRFVQKEISA-N
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
SMILES Code
OC(CCC1=C(C(C[C@@H]2NC([C@@H]([C@H]2C)CC)=O)=N/C1=C\C3=C(C(C)=C(N3)C[C@@H]4NC([C@@H]([C@H]4CC)C)=O)CCC(O)=O)C)=O.Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 631.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Guo X, Lin S, Zhang X, Li M, Wang Z, Peng Y, He X, Liu J. Integrated metabolomic and microbiome analysis identifies Cupriavidus metallidurans as a potential therapeutic target for β-thalassemia. Ann Hematol. 2024 Oct 1. doi: 10.1007/s00277-024-06016-z. Epub ahead of print. PMID: 39349606. 2: Delanghe JR, Van Elslande J, Godefroid MJ, Thieuw Barroso AM, De Buyzere ML, Maenhout TM. Colorimetric correcting for sample concentration in stool samples. Clin Chem Lab Med. 2024 Sep 23. doi: 10.1515/cclm-2024-0961. Epub ahead of print. PMID: 39301583. 3: Yang Z, Liu S, Wei F, Hu J. The effects of Qingchang Ligan formula on hepatic encephalopathy in mouse model: results from gut microbiome-metabolomics analysis. Front Cell Infect Microbiol. 2024 Aug 16;14:1381209. doi: 10.3389/fcimb.2024.1381209. PMID: 39220284; PMCID: PMC11362135. 4: Cho S, Cheruzel L, Cai J, Wrigley SK, Gemmell RT, Kokubun T, Steele JCP, Salphati L, Zhang D, Khojasteh SC. Discovery of Unprecedented Human Stercobilin Conjugates. Drug Metab Dispos. 2024 Aug 14;52(9):981-987. doi: 10.1124/dmd.124.001725. PMID: 38991780. 5: Zheng HY, Wang L, Zhang R, Ding R, Yang CX, Du ZQ. Valine induces inflammation and enhanced adipogenesis in lean mice by multi-omics analysis. Front Nutr. 2024 May 13;11:1379390. doi: 10.3389/fnut.2024.1379390. PMID: 38803448; PMCID: PMC11128663. 6: Jiang S, Xu L, Chen Y, Shu Z, Lv L, Zhao Y, Bi K, Yang S, Wang Q, Li L. Longitudinal gut fungal alterations and potential fungal biomarkers for the progression of primary liver disease. Sci China Life Sci. 2024 Jun;67(6):1183-1198. doi: 10.1007/s11427-023-2458-1. Epub 2024 Feb 26. PMID: 38413553. 7: Li D, Xia W, Cui X, Zhao M, Huang K, Wang X, Shen J, Chen H, Zhu L. The putatively high-altitude adaptation of macaque monkeys: Evidence from the fecal metabolome and gut microbiome. Evol Appl. 2023 Sep 25;16(10):1708-1720. doi: 10.1111/eva.13595. PMID: 38020871; PMCID: PMC10660799. 8: Sherwin A, Shaw IC. Sixty years of conjecture over a urinary biomarker: a step closer to understanding the proposed link between anxiety and urinary pyrroles. Lab Med. 2024 May 2;55(3):334-340. doi: 10.1093/labmed/lmad086. PMID: 37699019; PMCID: PMC11064097. 9: Liu X, Hu Q, Xu T, Yuan Q, Hu Q, Hu N, Sun W, Bai Y, Liu L, Feng J, Yi Q. Fndc5/irisin deficiency leads to dysbiosis of gut microbiota contributing to the depressive-like behaviors in mice. Brain Res. 2023 Nov 15;1819:148537. doi: 10.1016/j.brainres.2023.148537. Epub 2023 Aug 15. PMID: 37591459. 10: Wang Q, Xu K, Cai X, Wang C, Cao Y, Xiao J. Rosmarinic Acid Restores Colonic Mucus Secretion in Colitis Mice by Regulating Gut Microbiota-Derived Metabolites and the Activation of Inflammasomes. J Agric Food Chem. 2023 Mar 22;71(11):4571-4585. doi: 10.1021/acs.jafc.2c08444. Epub 2023 Mar 7. PMID: 36883243. 11: Dai Z, Li S, Meng Y, Zhao Q, Zhang Y, Suonan Z, Sun Y, Shen Q, Liao X, Xue Y. Capsaicin Ameliorates High-Fat Diet-Induced Atherosclerosis in ApoE-/- Mice via Remodeling Gut Microbiota. Nutrients. 2022 Oct 17;14(20):4334. doi: 10.3390/nu14204334. PMID: 36297020; PMCID: PMC9611743. 12: Prakash S, Mishra AK. Rapid and sensitive naked eye detection of faecal pigments using their enhanced solid-state green fluorescence on a zinc acetate substrate. Anal Methods. 2022 Aug 4;14(30):2907-2912. doi: 10.1039/d2ay00878e. PMID: 35861373. 13: Prakash S, Mishra AK. Photophysics of faecal pigments stercobilin and urobilin in aliphatic alcohols: introduction of a sensitive method for their detection using solvent phase extraction and fluorometry. Anal Methods. 2021 Dec 2;13(46):5573-5588. doi: 10.1039/d1ay01539g. PMID: 34787126. 14: Zöhrer PA, Hana CA, Seyed Khoei N, Mölzer C, Hörmann-Wallner M, Tosevska A, Doberer D, Marculescu R, Bulmer AC, Herbold CW, Berry D, Wagner KH. Gilbert's Syndrome and the Gut Microbiota - Insights From the Case-Control BILIHEALTH Study. Front Cell Infect Microbiol. 2021 Sep 16;11:701109. doi: 10.3389/fcimb.2021.701109. PMID: 34604105; PMCID: PMC8481893. 15: Prakash S, Panigrahi SK, Dorner RP, Wagner M, Schmidt W, Mishra AK. Understanding the photophysics of stercobilin-Zn(II) and urobilin-Zn(II) complexes towards faecal pigment analysis. Chemosphere. 2021 Feb;265:129189. doi: 10.1016/j.chemosphere.2020.129189. Epub 2020 Dec 8. PMID: 33307503. 16: Prakash S, Mishra AK. Stercobilin and Urobilin in Aqueous Media: Existence of Specific H-Aggregates and Nonspecific Higher Aggregates at Different Concentrations. J Phys Chem A. 2020 Dec 3;124(48):10053-10065. doi: 10.1021/acs.jpca.0c08642. Epub 2020 Nov 19. PMID: 33211965. 17: Sanada S, Suzuki T, Nagata A, Hashidume T, Yoshikawa Y, Miyoshi N. Intestinal microbial metabolite stercobilin involvement in the chronic inflammation of ob/ob mice. Sci Rep. 2020 Apr 15;10(1):6479. doi: 10.1038/s41598-020-63627-y. PMID: 32296105; PMCID: PMC7160104. 18: Ghidinelli S, Abbate S, Boiadjiev SE, Lightner DA, Longhi G. l-Stercobilin- HCl and d-Urobilin-HCl. Analysis of Their Chiroptical and Conformational Properties by VCD, ECD, and CPL Experiments and MD and DFT Calculations. J Phys Chem B. 2018 Dec 27;122(51):12351-12362. doi: 10.1021/acs.jpcb.8b07954. Epub 2018 Dec 17. PMID: 30489076. 19: Coffey JM, Vadas AJ, Puleo TR, Lewis KP, Pirrone GF, Rudolph HL, Helms ED, Wood TD, Flynn-Charlebois A. Synthesis and characterization of a deuterium labeled stercobilin: A potential biomarker for autism. J Labelled Comp Radiopharm. 2018 May 14. doi: 10.1002/jlcr.3629. Epub ahead of print. PMID: 29761558. 20: Hamoud AR, Weaver L, Stec DE, Hinds TD Jr. Bilirubin in the Liver-Gut Signaling Axis. Trends Endocrinol Metab. 2018 Mar;29(3):140-150. doi: 10.1016/j.tem.2018.01.002. Epub 2018 Feb 3. PMID: 29409713; PMCID: PMC5831340.

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