MedKoo Cat#: 598373 | Name: Fumitremorgin B
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Description:

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

Fumitremorgin B is intermediary in TR-2 mycotoxin biosyn.

Chemical Structure

Fumitremorgin B
Fumitremorgin B
CAS#12626-17-4

Theoretical Analysis

MedKoo Cat#: 598373

Name: Fumitremorgin B

CAS#: 12626-17-4

Chemical Formula: C27H33N3O5

Exact Mass: 479.2420

Molecular Weight: 479.57

Elemental Analysis: C, 67.62; H, 6.94; N, 8.76; O, 16.68

Price and Availability

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1mg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Fumitremorgin B; Lanosulin; Fumitremorgen B;
IUPAC/Chemical Name
(5aR,6S,12S,14aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione
InChi Key
WEIYXEFMCIRZHC-MWGWWEMPSA-N
InChi Code
InChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3/t19-,21-,24-,27+/m0/s1
SMILES Code
O=C([C@]1(O)[C@@H](O)C2=C([C@H](/C=C(C)\C)N13)N(C/C=C(C)\C)C4=C2C=CC(OC)=C4)N5[C@](CCC5)([H])C3=O
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 479.57 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: Liu J, Yang ZJ, Meng ZH. The isolation, purification and identification of fumitremorgin B produced by Aspergillus fumigatus. Biomed Environ Sci. 1996 Mar;9(1):1-11. PubMed PMID: 8721621. 2: Liu J, Yang Z, Meng Z. [Preparation of fumitremorgin B]. Zhonghua Yu Fang Yi Xue Za Zhi. 1996 Sep;30(5):282-5. Chinese. PubMed PMID: 9388887. 3: Liu J, Meng ZH. Production and characterization of monoclonal antibodies against fumitremorgin B. Biomed Environ Sci. 1998 Dec;11(4):336-44. PubMed PMID: 10095931. 4: Yamazaki M, Suzuki S. Toxicology of tremorgenic mycotoxins, fumitremorgin A and B. Dev Toxicol Environ Sci. 1986;12:273-82. PubMed PMID: 2881766. 5: Liu J, Yang ZJ, Meng ZH. The preparation and identification of fumitremorgin B-hemisuccinate-carrier proteins. Biomed Environ Sci. 1996 Mar;9(1):12-6. PubMed PMID: 8721622. 6: Grundmann A, Kuznetsova T, Afiyatullov SSh, Li SM. FtmPT2, an N-prenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B. Chembiochem. 2008 Sep 1;9(13):2059-63. doi: 10.1002/cbic.200800240. PubMed PMID: 18683158. 7: Wang X, Su H, Liu Y. Insights into the unprecedented epoxidation mechanism of fumitremorgin B endoperoxidase (FtmOx1) from Aspergillus fumigatus by QM/MM calculations. Phys Chem Chem Phys. 2017 Mar 15;19(11):7668-7677. doi: 10.1039/c7cp00313g. PubMed PMID: 28256663. 8: Yan W, Song H, Song F, Guo Y, Wu CH, Her AS, Pu Y, Wang S, Naowarojna N, Weitz A, Hendrich MP, Costello CE, Zhang L, Liu P, Zhang YJ. Endoperoxide formation by an α-ketoglutarate-dependent mononuclear non-haem iron enzyme. Nature. 2015 Nov 26;527(7579):539-543. doi: 10.1038/nature15519. Epub 2015 Nov 2. PubMed PMID: 26524521; PubMed Central PMCID: PMC4804460. 9: Wollinsky B, Li SM. Detection and purification of non-ribosomal peptide synthetase products in Neosartorya fischeri. Methods Mol Biol. 2012;944:111-9. doi: 10.1007/978-1-62703-122-6_7. PubMed PMID: 23065611. 10: Sabater-Vilar M, Nijmeijer S, Fink-Gremmels J. Genotoxicity assessment of five tremorgenic mycotoxins (fumitremorgen B, paxilline, penitrem A, verruculogen, and verrucosidin) produced by molds isolated from fermented meats. J Food Prot. 2003 Nov;66(11):2123-9. PubMed PMID: 14627292. 11: Willingale J, Perera KP, Mantle PG. An intermediary role for the tremorgenic mycotoxin TR-2 in the biosynthesis of verruculogen. Biochem J. 1983 Sep 15;214(3):991-3. PubMed PMID: 6626168; PubMed Central PMCID: PMC1152342. 12: dos Santos VM, Dorner JW, Carreira F. Isolation and toxigenicity of Aspergillus fumigatus from moldy silage. Mycopathologia. 2003;156(2):133-8. PubMed PMID: 12733634. 13: di Menna ME, Lauren DR, Wyatt PA. Effect of culture conditions on tremorgen production by some Penicillium species. Appl Environ Microbiol. 1986 Apr;51(4):821-4. PubMed PMID: 3707124; PubMed Central PMCID: PMC238967.