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MedKoo Cat#: 412794 | Name: Chaetomellic acid A

Description:

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

Chaetomellic acid A is a potent inhibitor of farnesyltransferase in isolated enzyme assays (IC50=55nM) but is inactive in whole cells. Inhibition of farnesyltransferase is selective over geranylgeranyltransferase I and II (IC50=92µM and 34µM respectively).

Chemical Structure

Chaetomellic acid A
Chaetomellic acid A
CAS#148796-51-4

Theoretical Analysis

MedKoo Cat#: 412794

Name: Chaetomellic acid A

CAS#: 148796-51-4

Chemical Formula: C19H34O4

Exact Mass: 326.2457

Molecular Weight: 326.48

Elemental Analysis: C, 69.90; H, 10.50; O, 19.60

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.
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Synonym
Chaetomellic acid A
IUPAC/Chemical Name
2-methyl-3-tetradecylmaleic acid
InChi Key
ULSDRNDLXFVDED-MSUUIHNZSA-N
InChi Code
InChI=1S/C19H34O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17(19(22)23)16(2)18(20)21/h3-15H2,1-2H3,(H,20,21)(H,22,23)/b17-16-
SMILES Code
CCCCCCCCCCCCCC/C(C(O)=O)=C(C(O)=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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 326.48 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: Nogueira A, Peixoto F, Oliveira MM, Pires CA, Colaço B, Oliveira PA, Pires MJ. The Effects of Long-Term Chaetomellic Acid A Administration on Renal Function and Oxidative Stress in a Rat Model of Renal Mass Reduction. Biomed Res Int. 2017;2017:5125980. doi: 10.1155/2017/5125980. Epub 2017 Feb 23. PMID: 28326323; PMCID: PMC5343227. 2: Bellesia F, Choi SR, Felluga F, Fiscaletti G, Ghelfi F, Menziani MC, Parsons AF, Poulter CD, Roncaglia F, Sabbatini M, Spinelli D. Novel route to chaetomellic acid A and analogues: serendipitous discovery of a more competent FTase inhibitor. Bioorg Med Chem. 2013 Jan 1;21(1):348-58. doi: 10.1016/j.bmc.2012.10.034. Epub 2012 Oct 29. PMID: 23182215; PMCID: PMC3761967. 3: Ratemi ES, Dolence JM, Poulter CD, Vederas JC. Synthesis of Protein Farnesyltransferase and Protein Geranylgeranyltransferase Inhibitors: Rapid Access to Chaetomellic Acid A and Its Analogues. J Org Chem. 1996 Sep 6;61(18):6296-6301. doi: 10.1021/jo960699k. PMID: 11667470. 4: Argade NP, Naik RH. A simple and efficient synthesis of the ras farnesyl- protein transferase inhibitor chaetomellic acid A. Bioorg Med Chem. 1996 Jun;4(6):881-3. doi: 10.1016/0968-0896(96)00076-4. PMID: 8818238. 5: Nogueira A, Vala H, Vasconcelos-Nóbrega C, Faustino-Rocha AI, Pires CA, Colaço A, Oliveira PA, Pires MJ. Long-term treatment with chaethomellic acid A reduces glomerulosclerosis and arteriolosclerosis in a rat model of chronic kidney disease. Biomed Pharmacother. 2017 Dec;96:489-496. doi: 10.1016/j.biopha.2017.09.137. Epub 2017 Oct 12. PMID: 29032332. 6: Kar A, Argade NP. A facile synthesis of natural products chaetomellic acid A and 1,7(Z)- nonadecadiene-2,3-dicarboxylic acid. J Org Chem. 2002 Oct 4;67(20):7131-4. doi: 10.1021/jo020195o. PMID: 12354009. 7: Singh SB, Jayasuriya H, Silverman KC, Bonfiglio CA, Williamson JM, Lingham RB. Efficient syntheses, human and yeast farnesyl-protein transferase inhibitory activities of chaetomellic acids and analogues. Bioorg Med Chem. 2000 Mar;8(3):571-80. doi: 10.1016/s0968-0896(99)00312-0. PMID: 10732974. 8: Garneau S, Qiao L, Chen L, Walker S, Vederas JC. Synthesis of mono- and disaccharide analogs of moenomycin and lipid II for inhibition of transglycosylase activity of penicillin-binding protein 1b. Bioorg Med Chem. 2004 Dec 15;12(24):6473-94. doi: 10.1016/j.bmc.2004.09.019. PMID: 15556765. 9: Lingham RB, Silverman KC, Bills GF, Cascales C, Sanchez M, Jenkins RG, Gartner SE, Martin I, Diez MT, Peláez F, et al. Chaetomella acutiseta produces chaetomellic acids A and B which are reversible inhibitors of farnesyl-protein transferase. Appl Microbiol Biotechnol. 1993 Nov;40(2-3):370-4. doi: 10.1007/BF00170395. PMID: 7764394. 10: Gibbs JB, Pompliano DL, Mosser SD, Rands E, Lingham RB, Singh SB, Scolnick EM, Kohl NE, Oliff A. Selective inhibition of farnesyl-protein transferase blocks ras processing in vivo. J Biol Chem. 1993 Apr 15;268(11):7617-20. PMID: 8463291.