MedKoo Cat#: 599189 | Name: Longestin

Description:

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

Longestin is a trypanocidal agent; isolated from Steptomyces argenteolus; inhibits brain calcium- and calmodulin-dependent cyclic nucleotide phosphodiesterase.

Chemical Structure

Longestin
Longestin
CAS#131774-53-3

Theoretical Analysis

MedKoo Cat#: 599189

Name: Longestin

CAS#: 131774-53-3

Chemical Formula: C61H88O17

Exact Mass: 1092.6022

Molecular Weight: 1093.35

Elemental Analysis: C, 67.01; H, 8.11; O, 24.88

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 #
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Synonym
Longestin; KS-505a; KS 505a; KS505a;
IUPAC/Chemical Name
2-((6-carboxy-4,5-dihydroxy-3-methoxytetrahydro-2H-pyran-2-yl)oxy)-14-hydroxy-8a,10a-bis(hydroxymethyl)-14-(3-methoxy-3-oxopropyl)-1,4,4a,6,6a,17b,19b,21b-octamethyl-16-oxo-2,3,4,4a,4b,5,6,6a,6b,7,8,8a,8b,9,10,10a,14,16,17,17a,17b,18,19,19a,19b,20,21,21a,21b,22,23,23a-dotriacontahydro-1H-benzo[9,10]piceno[3,4-a]furo[3,4-j]xanthene-1-carboxylic acid
InChi Key
DBIAGVXGCNWASW-UHFFFAOYSA-N
InChi Code
InChI=1S/C61H88O17/c1-30-25-40-54(4,21-15-39-57(40,7)31(2)26-42(58(39,8)52(70)71)75-51-48(74-10)46(66)45(65)47(76-51)49(67)68)35-13-19-53(3)36(56(30,35)6)16-22-59(28-62)37(53)14-20-55(5)38(59)17-23-60(29-63)41(55)27-32-34(77-60)12-11-33-44(32)50(69)78-61(33,72)24-18-43(64)73-9/h11-12,30-31,35-42,45-48,51,62-63,65-66,72H,13-29H2,1-10H3,(H,67,68)(H,70,71)
SMILES Code
CC1CC2C(C3C1(C)C4CCC5(CO)C(CCC6(C)C5CCC7(CO)C6Cc8c(C(OC9(O)CCC(OC)=O)=O)c9ccc8O7)C4(C)CC3)(C)CCC%10C2(C)C(C)CC(OC%11C(OC)C(O)C(O)C(C(O)=O)O%11)C%10(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
>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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,093.35 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: Hayashi Y, Onaka H, Itoh N, Seto H, Dairi T. Cloning of the gene cluster responsible for biosynthesis of KS-505a (longestin), a unique tetraterpenoid. Biosci Biotechnol Biochem. 2007 Dec;71(12):3072-81. Epub 2007 Dec 7. PubMed PMID: 18071268. 2: Dairi T. [Alternative menaquinone biosynthetic pathway operating in microorganisms]. Seikagaku. 2009 Feb;81(2):95-9. Japanese. PubMed PMID: 19306654. 3: Nakanishi S, Osawa K, Saito Y, Kawamoto I, Kuroda K, Kase H. KS-505a, a novel inhibitor of bovine brain Ca2+ and calmodulin-dependent cyclic-nucleotide phosphodiesterase from Streptomyces argenteolus. J Antibiot (Tokyo). 1992 Mar;45(3):341-7. PubMed PMID: 1374373. 4: Nagashima K, Toki S, Nakanishi S, Kase H, Matsuda Y. Neurite formation in NG108-15 neuroblastoma x glioma hybrid cells by KS-505a, a potent inhibitor of brain cyclic nucleotide phosphodiesterase. J Antibiot (Tokyo). 1993 Sep;46(9):1481-3. PubMed PMID: 7693640. 5: Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Masuma R, Shiomi K, Takahashi Y, Ichimura M, Yamada H, Omura S. In vitro and in vivo antitrypanosomal activitiy of two microbial metabolites, KS-505a and alazopeptin. J Antibiot (Tokyo). 2008 Oct;61(10):627-32. doi: 10.1038/ja.2008.83. PubMed PMID: 19168977. 6: Ozaki T, Shinde SS, Gao L, Okuizumi R, Liu C, Ogasawara Y, Lei X, Dairi T, Minami A, Oikawa H. Enzymatic Formation of a Skipped Methyl-Substituted Octaprenyl Side Chain of Longestin (KS-505a): Involvement of Homo-IPP as a Common Extender Unit. Angew Chem Int Ed Engl. 2018 May 28;57(22):6629-6632. doi: 10.1002/anie.201802116. Epub 2018 Apr 26. PubMed PMID: 29603559. 7: Ichimura M, Eiki R, Osawa K, Nakanishi S, Kase H. KS-505a, an isoform-selective inhibitor of calmodulin-dependent cyclic nucleotide phosphodiesterase. Biochem J. 1996 May 15;316 ( Pt 1):311-6. PubMed PMID: 8645223; PubMed Central PMCID: PMC1217340.