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

MedKoo CAT#: 597080

CAS#: 495-27-2

Description: Ophthalmic acid is a glutathione analog in which cysteine moiety is replaced by L-aminobutyrate.


Chemical Structure

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Ophthalmic acid
CAS# 495-27-2

Theoretical Analysis

MedKoo Cat#: 597080
Name: Ophthalmic acid
CAS#: 495-27-2
Chemical Formula: C11H19N3O6
Exact Mass: 289.13
Molecular Weight: 289.288
Elemental Analysis: C, 45.67; H, 6.62; N, 14.53; O, 33.18

Price and Availability

Size Price Availability Quantity
10mg USD 385 2 Weeks
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Synonym: Ophthalmic acid;

IUPAC/Chemical Name: N5-((S)-1-((carboxymethyl)amino)-1-oxobutan-2-yl)-L-glutamine

InChi Key: JCMUOFQHZLPHQP-BQBZGAKWSA-N

InChi Code: InChI=1S/C11H19N3O6/c1-2-7(10(18)13-5-9(16)17)14-8(15)4-3-6(12)11(19)20/h6-7H,2-5,12H2,1H3,(H,13,18)(H,14,15)(H,16,17)(H,19,20)/t6-,7-/m0/s1

SMILES Code: CC[C@H](NC(CC[C@H](N)C(O)=O)=O)C(NCC(O)=O)=O

Appearance: Solid powder

Purity: >96% (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: >2 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:

Product Data:
Biological target: Ophthalmic acid is a glutathione analog in which cysteine moiety is replaced by L-aminobutyrate.
In vitro activity: TBD
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 5.0 17.28
DMSO 5.0 17.28
Ethanol 12.0 41.48
PBS (pH 7.2) 3.0 10.37

Preparing Stock Solutions

The following data is based on the product molecular weight 289.29 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
Formulation protocol: TBD
In vitro protocol: TBD
In vivo protocol: TBD

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1: Servillo L, Castaldo D, Giovane A, Casale R, D'Onofrio N, Cautela D, Balestrieri ML. Ophthalmic acid is a marker of oxidative stress in plants as in animals. Biochim Biophys Acta. 2018 Apr;1862(4):991-998. doi: 10.1016/j.bbagen.2018.01.015. PubMed PMID: 29413907.

2: Ito T, Tokoro M, Hori R, Hemmi H, Yoshimura T. Production of Ophthalmic Acid Using Engineered Escherichia coli. Appl Environ Microbiol. 2018 Mar 19;84(7). pii: e02806-17. doi: 10.1128/AEM.02806-17. Print 2018 Apr 1. PubMed PMID: 29352090; PubMed Central PMCID: PMC5861832.

3: Lee J, Kang ES, Kobayashi S, Homma T, Sato H, Seo HG, Fujii J. The viability of primary hepatocytes is maintained under a low cysteine-glutathione redox state with a marked elevation in ophthalmic acid production. Exp Cell Res. 2017 Dec 1;361(1):178-191. doi: 10.1016/j.yexcr.2017.10.017. Epub 2017 Oct 26. PubMed PMID: 29079265.

4: Kobayashi S, Lee J, Takao T, Fujii J. Increased ophthalmic acid production is supported by amino acid catabolism under fasting conditions in mice. Biochem Biophys Res Commun. 2017 Sep 23;491(3):649-655. doi: 10.1016/j.bbrc.2017.07.149. Epub 2017 Jul 28. PubMed PMID: 28757411.

5: Servillo L, D'Onofrio N, Casale R, Cautela D, Giovane A, Castaldo D, Balestrieri ML. Ergothioneine products derived by superoxide oxidation in endothelial cells exposed to high-glucose. Free Radic Biol Med. 2017 Jul;108:8-18. doi: 10.1016/j.freeradbiomed.2017.03.009. Epub 2017 Mar 12. PubMed PMID: 28300670.

6: Irino Y, Toh R, Nagao M, Mori T, Honjo T, Shinohara M, Tsuda S, Nakajima H, Satomi-Kobayashi S, Shinke T, Tanaka H, Ishida T, Miyata O, Hirata KI. 2-Aminobutyric acid modulates glutathione homeostasis in the myocardium. Sci Rep. 2016 Nov 9;6:36749. doi: 10.1038/srep36749. PubMed PMID: 27827456; PubMed Central PMCID: PMC5101505.

7: Ito T, Yamauchi A, Hemmi H, Yoshimura T. Ophthalmic acid accumulation in an Escherichia coli mutant lacking the conserved pyridoxal 5'-phosphate-binding protein YggS. J Biosci Bioeng. 2016 Dec;122(6):689-693. doi: 10.1016/j.jbiosc.2016.06.010. Epub 2016 Jul 12. PubMed PMID: 27426274.

8: Chaleckis R, Murakami I, Takada J, Kondoh H, Yanagida M. Individual variability in human blood metabolites identifies age-related differences. Proc Natl Acad Sci U S A. 2016 Apr 19;113(16):4252-9. doi: 10.1073/pnas.1603023113. Epub 2016 Mar 28. PubMed PMID: 27036001; PubMed Central PMCID: PMC4843419.

9: Pluskal T, Sajiki K, Becker J, Takeda K, Yanagida M. Diverse fission yeast genes required for responding to oxidative and metal stress: Comparative analysis of glutathione-related and other defense gene deletions. Genes Cells. 2016 Jun;21(6):530-42. doi: 10.1111/gtc.12359. Epub 2016 Mar 23. PubMed PMID: 27005325.

10: Narainsamy K, Farci S, Braun E, Junot C, Cassier-Chauvat C, Chauvat F. Oxidative-stress detoxification and signalling in cyanobacteria: the crucial glutathione synthesis pathway supports the production of ergothioneine and ophthalmate. Mol Microbiol. 2016 Apr;100(1):15-24. doi: 10.1111/mmi.13296. Epub 2016 Feb 9. PubMed PMID: 26713511.

11: Kaur G, Leslie EM, Tillman H, Lee WM, Swanlund DP, Karvellas CJ; US Acute Liver Failure Study Group. Detection of Ophthalmic Acid in Serum from Acetaminophen-Induced Acute Liver Failure Patients Is More Frequent in Non-Survivors. PLoS One. 2015 Sep 25;10(9):e0139299. doi: 10.1371/journal.pone.0139299. eCollection 2015. PubMed PMID: 26407170; PubMed Central PMCID: PMC4583290.

12: Carretero A, León Z, García-Cañaveras JC, Zaragoza A, Gómez-Lechón MJ, Donato MT, Lahoz A. In vitro/in vivo screening of oxidative homeostasis and damage to DNA, protein, and lipids using UPLC/MS-MS. Anal Bioanal Chem. 2014 Sep;406(22):5465-76. doi: 10.1007/s00216-014-7983-5. Epub 2014 Jun 27. PubMed PMID: 24969468.

13: Brunelli L, Caiola E, Marabese M, Broggini M, Pastorelli R. Capturing the metabolomic diversity of KRAS mutants in non-small-cell lung cancer cells. Oncotarget. 2014 Jul 15;5(13):4722-31. PubMed PMID: 24952473; PubMed Central PMCID: PMC4148094.

14: Geenen S, du Preez FB, Snoep JL, Foster AJ, Sarda S, Kenna JG, Wilson ID, Westerhoff HV. Glutathione metabolism modeling: a mechanism for liver drug-robustness and a new biomarker strategy. Biochim Biophys Acta. 2013 Oct;1830(10):4943-59. doi: 10.1016/j.bbagen.2013.04.014. Epub 2013 Apr 30. PubMed PMID: 23643929.

15: Geenen S, Yates JW, Kenna JG, Bois FY, Wilson ID, Westerhoff HV. Multiscale modelling approach combining a kinetic model of glutathione metabolism with PBPK models of paracetamol and the potential glutathione-depletion biomarkers ophthalmic acid and 5-oxoproline in humans and rats. Integr Biol (Camb). 2013 Jun;5(6):877-88. doi: 10.1039/c3ib20245c. PubMed PMID: 23632663.

16: Dello SA, Neis EP, de Jong MC, van Eijk HM, Kicken CH, Olde Damink SW, Dejong CH. Systematic review of ophthalmate as a novel biomarker of hepatic glutathione depletion. Clin Nutr. 2013 Jun;32(3):325-30. doi: 10.1016/j.clnu.2012.10.008. Epub 2012 Oct 30. Review. PubMed PMID: 23182341.

17: Dello SA, van Eijk HM, Neis EP, de Jong MC, Olde Damink SW, Dejong CH. Ophthalmate detection in human plasma with LC-MS-MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Aug 15;903:1-6. doi: 10.1016/j.jchromb.2012.06.023. Epub 2012 Jun 26. PubMed PMID: 22831884.

18: Németi B, Anderson ME, Gregus Z. Glutathione synthetase promotes the reduction of arsenate via arsenolysis of glutathione. Biochimie. 2012 Jun;94(6):1327-33. doi: 10.1016/j.biochi.2012.02.033. Epub 2012 Mar 8. PubMed PMID: 22426003.

19: Carew MW, Naranmandura H, Shukalek CB, Le XC, Leslie EM. Monomethylarsenic diglutathione transport by the human multidrug resistance protein 1 (MRP1/ABCC1). Drug Metab Dispos. 2011 Dec;39(12):2298-304. doi: 10.1124/dmd.111.041673. Epub 2011 Sep 14. PubMed PMID: 21918036.

20: Geenen S, du Preez FB, Reed M, Nijhout HF, Kenna JG, Wilson ID, Westerhoff HV, Snoep JL. A mathematical modelling approach to assessing the reliability of biomarkers of glutathione metabolism. Eur J Pharm Sci. 2012 Jul 16;46(4):233-43. doi: 10.1016/j.ejps.2011.08.017. Epub 2011 Aug 24. PubMed PMID: 21888969.