MedKoo Cat#: 571061 | Name: Leucettamol A

Description:

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

Leucettamol A is a A leukotriene B4 receptor antagonist isolated from the marine sponge Leucetta microraphis.It has a structure of a chiral long-chain "two-headed" sphingolipid (dimeric sphingolipid). It inhibits the formation of a complex composed of the ubiquitin E2 enzyme Ubc13 and Uev1A. The post-translational modification of proteins with ubiquitin (Ub) controls a number of fundamental processes within the cell, including protein degradation by the Ub−proteasome system (UPS). These inhibitors may be leads for anti-cancer agents and anti-rheumatoid arthritis agents.

Chemical Structure

Leucettamol A
Leucettamol A
CAS#151124-32-2

Theoretical Analysis

MedKoo Cat#: 571061

Name: Leucettamol A

CAS#: 151124-32-2

Chemical Formula: C30H52N2O2

Exact Mass: 472.4029

Molecular Weight: 472.76

Elemental Analysis: C, 76.22; H, 11.09; N, 5.93; O, 6.77

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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Related CAS #
No Data
Synonym
Leucettamol A; Leucettamine A
IUPAC/Chemical Name
5,8,11,14,17,20-Triacontahexaene-3,28-diol, 2,29-diamino-, (2R,3S,5Z,8Z,11Z,14Z,20Z,28S,29R)-rel-
InChi Key
CXFKWMQQNSTRAS-OGMHTJTFSA-N
InChi Code
InChI=1S/C30H52N2O2/c1-27(31)29(33)25-23-21-19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-22-24-26-30(34)28(2)32/h3,5-6,8-9,11-12,14-15,17,21,23,27-30,33-34H,4,7,10,13,16,18-20,22,24-26,31-32H2,1-2H3/b5-3-,8-6+,11-9-,14-12-,17-15-,23-21-/t27-,28-,29+,30+/m1/s1
SMILES Code
C[C@@H](N)[C@@H](O)C/C=C\C/C=C\C/C=C\C/C=C\C/C=C/C/C=C\CCCCCC[C@H](O)[C@H](N)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
Inflammatory cytokines, such as interleukin-1 (IL-1), IL-6, and TNF-α, are abundant in the synovial tissue and synovial fluid of patients with RA. Thus, NF-κB is regarded as an ideal target for anti-RA. NF-κB is a protein complex that controls the transcription of DNA, cytokine production, and cell survival. Incorrect regulation of NF-κB has been linked to cancer, inflammation, autoimmune diseases, septic shock, viral infection, and improper immune development. Among most cell types, NF- κB is sequestered in the cytoplasm in an inactive form associated with inhibitors of NF-κB (IκB). The activation of NF-κB pathway is dependent on protein ubiquitination. Therefore, inhibitors of ubiquitination may suppress the activation of the NF-κB signaling pathway. Ubiquitination is an enzymatic post-translational modification in which a ubiquitin protein is attached to a substrate protein.

Preparing Stock Solutions

The following data is based on the product molecular weight 472.76 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: Chen H, Wu G, Gao S, Guo R, Zhao Z, Yuan H, Liu S, Wu J, Lu X, Yuan X, Yu Z, Zu X, Xie N, Yang N, Hu Z, Sun Q, Zhang W. Discovery of Potent Small-Molecule Inhibitors of Ubiquitin-Conjugating Enzyme UbcH5c from α-Santonin Derivatives. J Med Chem. 2017 Aug 2. doi: 10.1021/acs.jmedchem.6b01829. [Epub ahead of print] PubMed PMID: 28696694. 2: Dalisay DS, Tsukamoto S, Molinski TF. Absolute configuration of the alpha,omega bifunctionalized sphingolipid leucettamol A from Leucetta microrhaphis by deconvoluted exciton coupled CD. J Nat Prod. 2009 Mar 27;72(3):353-9. doi: 10.1021/np800549n. PubMed PMID: 19159253; PubMed Central PMCID: PMC2765480. 3: Ushiyama S, Umaoka H, Kato H, Suwa Y, Morioka H, Rotinsulu H, Losung F, Mangindaan RE, de Voogd NJ, Yokosawa H, Tsukamoto S. Manadosterols A and B, sulfonated sterol dimers inhibiting the Ubc13-Uev1A interaction, isolated from the marine sponge Lissodendryx fibrosa. J Nat Prod. 2012 Aug 24;75(8):1495-9. doi: 10.1021/np300352u. Epub 2012 Aug 8. PubMed PMID: 22873794. 4: Tsukamoto S, Takeuchi T, Rotinsulu H, Mangindaan RE, van Soest RW, Ukai K, Kobayashi H, Namikoshi M, Ohta T, Yokosawa H. Leucettamol A: a new inhibitor of Ubc13-Uev1A interaction isolated from a marine sponge, Leucetta aff. microrhaphis. Bioorg Med Chem Lett. 2008 Dec 15;18(24):6319-20. doi: 10.1016/j.bmcl.2008.10.110. Epub 2008 Oct 31. PubMed PMID: 19006668. 5: Crews P, Clark DP, Tenney K. Variation in the alkaloids among indo-pacific Leucetta sponges. J Nat Prod. 2003 Feb;66(2):177-82. PubMed PMID: 12608847. 6: Abdjul DB, Yamazaki H, Kanno SI, Tomizawa A, Rotinsulu H, Wewengkang DS, Sumilat DA, Ukai K, Kapojos MM, Namikoshi M. An anti-mycobacterial bisfunctionalized sphingolipid and new bromopyrrole alkaloid from the Indonesian marine sponge Agelas sp. J Nat Med. 2017 Jul;71(3):531-536. doi: 10.1007/s11418-017-1085-6. Epub 2017 Mar 31. PubMed PMID: 28364227. 7: Chianese G, Fattorusso E, Putra MY, Calcinai B, Bavestrello G, Moriello AS, De Petrocellis L, Di Marzo V, Taglialatela-Scafati O. Leucettamols, bifunctionalized marine sphingoids, act as modulators of TRPA1 and TRPM8 channels. Mar Drugs. 2012 Nov 2;10(11):2435-47. doi: 10.3390/md10112435. PubMed PMID: 23203269; PubMed Central PMCID: PMC3509527.