Ovothiol A | CAS#108418-13-9 | antioxidant

MedKoo Cat#: 597339 | Name: Ovothiol A

Description:

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

Ovothiol A (N1-methyl-4-mercaptohistidine) is a highly reducing antioxidant mercaptohistidine, which accumulates to very high levels in the eggs of certain marine invertebrates, including sea urchins, scallops and starfish, where it acts to scavenge hydrogen peroxide released during fertilization. This thiol is also found in some human pathogens including trypanosomes and members of the genus Leishmania. The anti-ulcerogenic activity of ovothiol A includes scavenging free radicals, inhibition of inflammation, regulation of apoptosis, and stabilization of fibroblast growth factors to promote gastric ulcers healing.

Chemical Structure

Ovothiol A

CAS#108418-13-9

Theoretical Analysis

MedKoo Cat#: 597339

Name: Ovothiol A

CAS#: 108418-13-9

Chemical Formula: C7H11N3O2S

Exact Mass: 201.0572

Molecular Weight: 201.24

Elemental Analysis: C, 41.78; H, 5.51; N, 20.88; O, 15.90; S, 15.93

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Ovothiol A; U23; U 23; U-23;

IUPAC/Chemical Name

(S)-2-amino-3-(4-mercapto-1-methyl-1H-imidazol-5-yl)propanoic acid

InChi Key

XWKKYVJREGXHFO-BYPYZUCNSA-N

InChi Code

InChI=1S/C7H11N3O2S/c1-10-3-9-6(13)5(10)2-4(8)7(11)12/h3-4,13H,2,8H2,1H3,(H,11,12)/t4-/m0/s1

SMILES Code

N[C@@H](CC1=C(S)N=CN1C)C(O)=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 201.24 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: Salaheldin AT, Shehata MR, Sakr HI, Atia T, Mohamed AS. Therapeutic Potency of Ovothiol A on Ethanol-Induced Gastric Ulcers in Wistar Rats. Mar Drugs. 2022 Dec 28;21(1):25. doi: 10.3390/md21010025. PMID: 36662198; PMCID: PMC9862145. 2: Leo P, Spragg J, Wakefield J, Swart J. Predictors of cycling performance success: Traditional approaches and a novel method to assess performance capacity in U23 road cyclists. J Sci Med Sport. 2023 Jan;26(1):52-57. doi: 10.1016/j.jsams.2022.11.005. Epub 2022 Dec 1. PMID: 36513568. 3: Leo P, Simon D, Hovorka M, Lawley J, Mujika I. Elite versus non-elite cyclist - Stepping up to the international/elite ranks from U23 cycling. J Sports Sci. 2022 Aug;40(16):1874-1884. doi: 10.1080/02640414.2022.2117394. Epub 2022 Aug 30. PMID: 36040014. 4: Mohammed EN, Soliman AM, Mohamed AS. Modulatory effect of Ovothiol-A on myocardial infarction induced by epinephrine in rats. J Food Biochem. 2022 Sep;46(9):e14296. doi: 10.1111/jfbc.14296. Epub 2022 Jul 5. PMID: 35791516. 5: Cordell GA, Lamahewage SNS. Ergothioneine, Ovothiol A, and Selenoneine- Histidine-Derived, Biologically Significant, Trace Global Alkaloids. Molecules. 2022 Apr 21;27(9):2673. doi: 10.3390/molecules27092673. PMID: 35566030; PMCID: PMC9103826. 6: Osik NA, Zelentsova EA, Tsentalovich YP. Kinetic Studies of Antioxidant Properties of Ovothiol A. Antioxidants (Basel). 2021 Sep 15;10(9):1470. doi: 10.3390/antiox10091470. PMID: 34573105; PMCID: PMC8470380. 7: Leo P, Spragg J, Simon D, Lawley J, Mujika I. Climbing Performance in U23 and Professional Cyclists during a Multi-stage Race. Int J Sports Med. 2022 Feb;43(2):161-167. doi: 10.1055/a-1524-2656. Epub 2021 Jul 15. Erratum in: Int J Sports Med. 2021 Aug 11;: PMID: 34265861. 8: Leo P, Spragg J, Mujika I, Giorgi A, Lorang D, Simon D, Lawley JS. Power Profiling, Workload Characteristics, and Race Performance of U23 and Professional Cyclists During the Multistage Race Tour of the Alps. Int J Sports Physiol Perform. 2021 Aug 1;16(8):1089–1095. doi: 10.1123/ijspp.2020-0381. Epub 2021 Mar 31. PMID: 33789246. 9: Leo P, Spragg J, Mujika I, Menz V, Lawley JS. Power Profiling in U23 Professional Cyclists During a Competitive Season. Int J Sports Physiol Perform. 2021 Jun 1;16(6):881-889. doi: 10.1123/ijspp.2020-0200. Epub 2021 Feb 19. PMID: 33607626. 10: Tsentalovich YP, Zelentsova EA, Yanshole LV, Yanshole VV, Odud IM. Most abundant metabolites in tissues of freshwater fish pike-perch (Sander lucioperca). Sci Rep. 2020 Oct 13;10(1):17128. doi: 10.1038/s41598-020-73895-3. PMID: 33051472; PMCID: PMC7555489. 11: Goncharenko KV, Flückiger S, Liao C, Lim D, Stampfli AR, Seebeck FP. Selenocysteine as a Substrate, an Inhibitor and a Mechanistic Probe for Bacterial and Fungal Iron-Dependent Sulfoxide Synthases. Chemistry. 2020 Jan 27;26(6):1328-1334. doi: 10.1002/chem.201903898. Epub 2020 Jan 20. PMID: 31545545. 12: Yanshole VV, Yanshole LV, Zelentsova EA, Tsentalovich YP. Ovothiol A is the Main Antioxidant in Fish Lens. Metabolites. 2019 May 10;9(5):95. doi: 10.3390/metabo9050095. PMID: 31083459; PMCID: PMC6572425. 13: Brancaccio M, D'Argenio G, Lembo V, Palumbo A, Castellano I. Antifibrotic Effect of Marine Ovothiol in an In Vivo Model of Liver Fibrosis. Oxid Med Cell Longev. 2018 Dec 17;2018:5045734. doi: 10.1155/2018/5045734. PMID: 30647809; PMCID: PMC6311726. 14: Naowarojna N, Huang P, Cai Y, Song H, Wu L, Cheng R, Li Y, Wang S, Lyu H, Zhang L, Zhou J, Liu P. In Vitro Reconstitution of the Remaining Steps in Ovothiol A Biosynthesis: C-S Lyase and Methyltransferase Reactions. Org Lett. 2018 Sep 7;20(17):5427-5430. doi: 10.1021/acs.orglett.8b02332. Epub 2018 Aug 24. PMID: 30141637. 15: Castellano I, Seebeck FP. On ovothiol biosynthesis and biological roles: from life in the ocean to therapeutic potential. Nat Prod Rep. 2018 Dec 12;35(12):1241-1250. doi: 10.1039/c8np00045j. PMID: 30052250. 16: Castellano I, Di Tomo P, Di Pietro N, Mandatori D, Pipino C, Formoso G, Napolitano A, Palumbo A, Pandolfi A. Anti-Inflammatory Activity of Marine Ovothiol A in an In Vitro Model of Endothelial Dysfunction Induced by Hyperglycemia. Oxid Med Cell Longev. 2018 Apr 19;2018:2087373. doi: 10.1155/2018/2087373. PMID: 29849868; PMCID: PMC5932987. 17: Castellano I, Migliaccio O, D'Aniello S, Merlino A, Napolitano A, Palumbo A. Shedding light on ovothiol biosynthesis in marine metazoans. Sci Rep. 2016 Feb 26;6:21506. doi: 10.1038/srep21506. PMID: 26916575; PMCID: PMC4768315. 18: Mirzahosseini A, Orgován G, Tóth G, Hosztafi S, Noszál B. The complete microspeciation of ovothiol A disulfide: a hexabasic symmetric biomolecule. J Pharm Biomed Anal. 2015 Mar 25;107:209-16. doi: 10.1016/j.jpba.2014.12.029. Epub 2014 Dec 24. PMID: 25594898. 19: Russo GL, Russo M, Castellano I, Napolitano A, Palumbo A. Ovothiol isolated from sea urchin oocytes induces autophagy in the Hep-G2 cell line. Mar Drugs. 2014 Jul 7;12(7):4069-85. doi: 10.3390/md12074069. PMID: 25003791; PMCID: PMC4113815. 20: Trochine A, Creek DJ, Faral-Tello P, Barrett MP, Robello C. Benznidazole biotransformation and multiple targets in Trypanosoma cruzi revealed by metabolomics. PLoS Negl Trop Dis. 2014 May 22;8(5):e2844. doi: 10.1371/journal.pntd.0002844. PMID: 24853684; PMCID: PMC4031082.