MedKoo Cat#: 592688 | Name: Pseudopterosin E

Description:

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

Pseudopterosin E has an effect against Mycobacterium tuberculosis and other pathogens.

Chemical Structure

 Pseudopterosin E
Pseudopterosin E
CAS#121011-80-1

Theoretical Analysis

MedKoo Cat#: 592688

Name: Pseudopterosin E

CAS#: 121011-80-1

Chemical Formula: C26H38O6

Exact Mass: 446.2668

Molecular Weight: 446.58

Elemental Analysis: C, 69.93; H, 8.58; O, 21.50

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
Pseudopterosin E
IUPAC/Chemical Name
alpha-L-Galactopyranoside, (1S,3R,7S,9aR)-2,3,7,8,9,9a-hexahydro-6-hydroxy-1,4,7-trimethyl-3-(2-methyl-1-propen-1-yl)-1H-phenalen-5-yl 6-deoxy-
InChi Key
LIAAPIYLHKRUNZ-BRPLUSLASA-N
InChi Code
InChI=1S/C26H38O6/c1-11(2)9-16-10-13(4)17-8-7-12(3)18-20(17)19(16)14(5)25(22(18)28)32-26-24(30)23(29)21(27)15(6)31-26/h9,12-13,15-17,21,23-24,26-30H,7-8,10H2,1-6H3/t12-,13-,15-,16-,17+,21+,23+,24-,26-/m0/s1
SMILES Code
O[C@@H]([C@@H]([C@@H]([C@H](C)O1)O)O)[C@@H]1OC2=C(C)C3=C4[C@]([C@@H](C)C[C@@H]3/C=C(C)\C)([H])CC[C@H](C)C4=C2O
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 446.58 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: McCulloch MW, Haltli B, Marchbank DH, Kerr RG. Evaluation of pseudopteroxazole and pseudopterosin derivatives against Mycobacterium tuberculosis and other pathogens. Mar Drugs. 2012 Aug;10(8):1711-28. Epub 2012 Aug 15. PubMed PMID: 23015770; PubMed Central PMCID: PMC3447335. 2: Newton CG, Sherburn MS. Total synthesis of the pseudopterosin aglycones. Nat Prod Rep. 2015 Jun;32(6):865-76. doi: 10.1039/c5np00008d. Review. PubMed PMID: 25882677. 3: Newton CG, Drew SL, Lawrence AL, Willis AC, Paddon-Row MN, Sherburn MS. Pseudopterosin synthesis from a chiral cross-conjugated hydrocarbon through a series of cycloadditions. Nat Chem. 2015 Jan;7(1):82-6. doi: 10.1038/nchem.2112. Epub 2014 Nov 17. PubMed PMID: 25515894. 4: Flachsmann F, Schellhaas K, Moya CE, Jacobs RS, Fenical W. Synthetic pseudopterosin analogues: A novel class of antiinflammatory drug candidates. Bioorg Med Chem. 2010 Dec 1;18(23):8324-33. doi: 10.1016/j.bmc.2010.09.067. Epub 2010 Oct 7. PubMed PMID: 21041093. 5: Lazerwith SE, Johnson TW, Corey EJ. Syntheses and stereochemical revision of pseudopterosin G-J aglycon and helioporin E. Org Lett. 2000 Jul 27;2(15):2389-92. PubMed PMID: 10930291. 6: Xiong M, Guo Z, Han B, Chen M. Combating multidrug resistance in bacterial infection by targeting functional proteome with natural products. Nat Prod Res. 2015;29(17):1624-9. doi: 10.1080/14786419.2014.991926. Epub 2014 Dec 18. PubMed PMID: 25518752. 7: Puyana M, Narvaez G, Paz A, Osorno O, Duque C. Pseudopterosin content variability of the purple sea whip Pseudopterogorgia elisabethae at the islands of San Andres and Providencia (SW Caribbean). J Chem Ecol. 2004 Jun;30(6):1183-201. PubMed PMID: 15303322. 8: Day DR, Jabaiah S, Jacobs RS, Little RD. Cyclodextrin formulation of the marine natural product pseudopterosin A uncovers optimal pharmacodynamics in proliferation studies of human umbilical vein endothelial cells. Mar Drugs. 2013 Aug 26;11(9):3258-71. doi: 10.3390/md11093258. PubMed PMID: 24065164; PubMed Central PMCID: PMC3806459. 9: Caplan SL, Zheng B, Dawson-Scully K, White CA, West LM. Pseudopterosin A: Protection of Synaptic Function and Potential as a Neuromodulatory Agent. Mar Drugs. 2016 Mar 10;14(3). pii: E55. doi: 10.3390/md14030055. PubMed PMID: 26978375; PubMed Central PMCID: PMC4820309. 10: Mayer AM, Jacobson PB, Fenical W, Jacobs RS, Glaser KB. Pharmacological characterization of the pseudopterosins: novel anti-inflammatory natural products isolated from the Caribbean soft coral, Pseudopterogorgia elisabethae. Life Sci. 1998;62(26):PL401-7. PubMed PMID: 9651113. 11: Mydlarz LD, Jacobs RS, Boehnlein J, Kerr RG. Pseudopterosin biosynthesis in Symbiodinium sp., the dinoflagellate symbiont of Pseudopterogorgia elisabethae. Chem Biol. 2003 Nov;10(11):1051-6. PubMed PMID: 14652072. 12: Thornton RS, Kerr RG. Induction of pseudopterosin biosynthesis in the gorgonian Pseudopterogorgia elisabethae. J Chem Ecol. 2002 Oct;28(10):2083-90. PubMed PMID: 12474901. 13: Kohl AC, Kerr RG. Identification and characterization of the pseudopterosin diterpene cyclase, elisabethatriene synthase, from the marine gorgonian, Pseudopterogorgia elisabethae. Arch Biochem Biophys. 2004 Apr 1;424(1):97-104. PubMed PMID: 15019841. 14: Rodríguez II, Shi YP, García OJ, Rodríguez AD, Mayer AM, Sánchez JA, Ortega-Barria E, González J. New pseudopterosin and seco-pseudopterosin diterpene glycosides from two Colombian isolates of Pseudopterogorgia elisabethae and their diverse biological activities. J Nat Prod. 2004 Oct;67(10):1672-80. PubMed PMID: 15497938. 15: Ferns TA, Kerr RG. Identification of amphilectosins as key intermediates in pseudopterosin biosynthesis. J Org Chem. 2005 Aug 5;70(16):6152-7. PubMed PMID: 16050671. 16: Ettouati WS, Jacobs RS. Effect of pseudopterosin A on cell division, cell cycle progression, DNA, and protein synthesis in cultured sea urchin embryos. Mol Pharmacol. 1987 May;31(5):500-5. PubMed PMID: 3574294. 17: Zhong W, Moya C, Jacobs RS, Little RD. Synthesis and an evaluation of the bioactivity of the C-glycoside of pseudopterosin A methyl ether. J Org Chem. 2008 Sep 19;73(18):7011-6. doi: 10.1021/jo801432t. Epub 2008 Aug 19. PubMed PMID: 18710290. 18: Kohl AC, Ata A, Kerr RG. Pseudopterosin biosynthesis-pathway elucidation, enzymology, and a proposed production method for anti-inflammatory metabolites from Pseudopterogorgia elisabethae. J Ind Microbiol Biotechnol. 2003 Aug;30(8):495-9. Epub 2003 Aug 14. PubMed PMID: 12920603. 19: Onumah N. A novel anti-inflammatory in treatment of acne vulgaris: the pseudopterosins. J Drugs Dermatol. 2013 Oct;12(10):1177-9. PubMed PMID: 24085056. 20: Kerr RG, Kohl AC, Ferns TA. Elucidation of the biosynthetic origin of the anti-inflammatory pseudopterosins. J Ind Microbiol Biotechnol. 2006 Jul;33(7):532-8. Epub 2006 Mar 23. Review. PubMed PMID: 16555072.