Adenanthin | CAS# 111917-59-0 | Antioxidant Inhibitor

MedKoo Cat#: 564546 | Name: Adenanthin

Description:

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

Adenanthin is a natural inhibitor of thiol-dependent antioxidant enzymes, impairing the effector functions of human natural killer cells.

Chemical Structure

Adenanthin

CAS#111917-59-0

Theoretical Analysis

MedKoo Cat#: 564546

Name: Adenanthin

CAS#: 111917-59-0

Chemical Formula: C26H34O9

Exact Mass: 490.2203

Molecular Weight: 490.55

Elemental Analysis: C, 63.66; H, 6.99; O, 29.35

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Synonym

Adenanthin A; Adenanthin-A; AdenanthinA

IUPAC/Chemical Name

(1S,3S,4aR,6R,6aR,9S,11S,11aS,11bS)-3-hydroxy-4,4,11b-trimethyl-8-methylene-5,7-dioxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-1,6,11-triyl triacetate

InChi Key

WQVYSFSBBFDGRG-FYHXSELJSA-N

InChi Code

InChI=1S/C26H34O9/c1-11-15-8-16(33-12(2)27)20-25(7)18(34-13(3)28)9-17(30)24(5,6)21(25)19(31)23(35-14(4)29)26(20,10-15)22(11)32/h15-18,20-21,23,30H,1,8-10H2,2-7H3/t15-,16+,17+,18+,20+,21-,23+,25+,26+/m1/s1

SMILES Code

O=C([C@]([C@H]1OC(C)=O)(C2)[C@]3([H])[C@]4(C)[C@@H](OC(C)=O)C[C@H](O)C(C)(C)[C@@]4([H])C1=O)C([C@]2([H])C[C@@H]3OC(C)=O)=C

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

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Certificate of Analysis

View CoA: current batch, Lot#A9O07B16

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 490.55 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.

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: Siernicka M, Winiarska M, Bajor M, Firczuk M, Muchowicz A, Bobrowicz M, Fauriat C, Golab J, Olive D, Zagozdzon R. Adenanthin, a new inhibitor of thiol-dependent antioxidant enzymes, impairs the effector functions of human natural killer cells. Immunology. 2015 Sep;146(1):173-83. doi: 10.1111/imm.12494. Epub 2015 Jul 8. PubMed PMID: 26094816; PubMed Central PMCID: PMC4552512. 2: Soethoudt M, Peskin AV, Dickerhof N, Paton LN, Pace PE, Winterbourn CC. Interaction of adenanthin with glutathione and thiol enzymes: selectivity for thioredoxin reductase and inhibition of peroxiredoxin recycling. Free Radic Biol Med. 2014 Dec;77:331-9. doi: 10.1016/j.freeradbiomed.2014.09.025. Epub 2014 Oct 5. PubMed PMID: 25289458. 3: Hou JK, Huang Y, He W, Yan ZW, Fan L, Liu MH, Xiao WL, Sun HD, Chen GQ. Adenanthin targets peroxiredoxin I/II to kill hepatocellular carcinoma cells. Cell Death Dis. 2014 Sep 4;5:e1400. doi: 10.1038/cddis.2014.345. PubMed PMID: 25188510; PubMed Central PMCID: PMC4540188. 4: Muchowicz A, Firczuk M, Chlebowska J, Nowis D, Stachura J, Barankiewicz J, Trzeciecka A, Kłossowski S, Ostaszewski R, Zagożdżon R, Pu JX, Sun HD, Golab J. Adenanthin targets proteins involved in the regulation of disulphide bonds. Biochem Pharmacol. 2014 May 15;89(2):210-6. doi: 10.1016/j.bcp.2014.02.022. Epub 2014 Mar 11. PubMed PMID: 24630929. 5: Yin QQ, Liu CX, Wu YL, Wu SF, Wang Y, Zhang X, Hu XJ, Pu JX, Lu Y, Zhou HC, Wang HL, Nie H, Sun HD, Chen GQ. Preventive and therapeutic effects of adenanthin on experimental autoimmune encephalomyelitis by inhibiting NF-κB signaling. J Immunol. 2013 Sep 1;191(5):2115-25. doi: 10.4049/jimmunol.1203546. PubMed PMID: 23964105. 6: Liu CX, Yin QQ, Zhou HC, Wu YL, Pu JX, Xia L, Liu W, Huang X, Jiang T, Wu MX, He LC, Zhao YX, Wang XL, Xiao WL, Chen HZ, Zhao Q, Zhou AW, Wang LS, Sun HD, Chen GQ. Adenanthin targets peroxiredoxin I and II to induce differentiation of leukemic cells. Nat Chem Biol. 2012 Apr 8;8(5):486-93. doi: 10.1038/nchembio.935. PubMed PMID: 22484541.