Viridicatumtoxin
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MedKoo CAT#: 461859

CAS#: 39277-41-3

Description: Viridicatumtoxin is a fungus-derived tetracycline-like antibiotic.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 970 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-08-10. Prices are subject to change without notice.

Viridicatumtoxin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461859
Name: Viridicatumtoxin
CAS#: 39277-41-3
Chemical Formula: C30H31NO10
Exact Mass: 565.1948
Molecular Weight: 565.57
Elemental Analysis: C, 63.71; H, 5.52; N, 2.48; O, 28.29


Synonym: Viridicatumtoxin; SC 28762; SC-28762; SC28762; Viriditoxin;

IUPAC/Chemical Name: (1R,7a'S,11a'S,12'S)-5',6',7a',10',11a',12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-7',7a',8',11',11a',12'-hexahydro-5'H-spiro[cyclohexane-1,2'-cyclopenta[de]tetracen]-2-ene-9'-carboxamide

InChi Key: YEAXHJGUSZXWQI-AKOCBNACSA-N

InChi Code: InChI=1S/C30H31NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8-9,13,23,32-35,39-40H,5,7,10H2,1-4H3,(H2,31,38)/t13?,23-,28+,29-,30+/m0/s1

SMILES Code: O=C(C(C([C@]12O)=O)=C(O)C[C@]1(O)[C@@H](O)C(C3=C[C@]4(C5=C3C(C(O)C=C5OC)=C6O)C(C)=CCCC4(C)C)=C6C2=O)N


Technical Data

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


References

1: Nicolaou KC, Hale CR, Nilewski C, Ioannidou HA, ElMarrouni A, Nilewski LG, Beabout K, Wang TT, Shamoo Y. Total synthesis of viridicatumtoxin B and analogues thereof: strategy evolution, structural revision, and biological evaluation. J Am Chem Soc. 2014 Aug 27;136(34):12137-60. doi: 10.1021/ja506472u. Epub 2014 Aug 15. PubMed PMID: 25317739; PubMed Central PMCID: PMC4210137.

2: Nicolaou KC, Nilewski C, Hale CR, Ioannidou HA, ElMarrouni A, Koch LG. Total synthesis and structural revision of viridicatumtoxin B. Angew Chem Int Ed Engl. 2013 Aug 12;52(33):8736-41. doi: 10.1002/anie.201304691. Epub 2013 Jul 24. PubMed PMID: 23893651; PubMed Central PMCID: PMC3835450.

3: Zheng CJ, Yu HE, Kim EH, Kim WG. Viridicatumtoxin B, a new anti-MRSA agent from Penicillium sp. FR11. J Antibiot (Tokyo). 2008 Oct;61(10):633-7. doi: 10.1038/ja.2008.84. PubMed PMID: 19168978.

4: Chooi YH, Cacho R, Tang Y. Identification of the viridicatumtoxin and griseofulvin gene clusters from Penicillium aethiopicum. Chem Biol. 2010 May 28;17(5):483-94. doi: 10.1016/j.chembiol.2010.03.015. PubMed PMID: 20534346; PubMed Central PMCID: PMC2884005.

5: Inokoshi J, Nakamura Y, Komada S, Komatsu K, Umeyama H, Tomoda H. Inhibition of bacterial undecaprenyl pyrophosphate synthase by small fungal molecules. J Antibiot (Tokyo). 2016 Nov;69(11):798-805. doi: 10.1038/ja.2016.35. Epub 2016 Apr 6. PubMed PMID: 27049441.

6: Shang Z, Salim AA, Khalil Z, Quezada M, Bernhardt PV, Capon RJ. Viridicatumtoxins: Expanding on a Rare Tetracycline Antibiotic Scaffold. J Org Chem. 2015 Dec 18;80(24):12501-8. doi: 10.1021/acs.joc.5b02367. Epub 2015 Dec 7. PubMed PMID: 26605854.

7: Bendele AM, Carlton WW, Nelson GE, Peterson RE, Grove MD. Viridicatumtoxin mycotoxicosis in mice and rats. Toxicol Lett. 1984 Sep;22(3):287-91. PubMed PMID: 6485002.

8: Bolin DC, Carlton WW, Peterson RE, Grove MD. Studies of the teratogenicity of xanthomegnin and viridicatumtoxin in ICR mice. Toxicol Lett. 1991 Mar;55(3):273-7. PubMed PMID: 2003269.

9: Hutchison RD, Steyn PS, Van Rensburg SJ. Viridicatumtoxin, a new mycotoxin from Penicillium viridicatum Westling. Toxicol Appl Pharmacol. 1973 Mar;24(3):507-9. PubMed PMID: 4122267.

10: Tomoda H. [Mode of action of microbial anti-MRSA agents]. Yakugaku Zasshi. 2012;132(1):37-44. Review. Japanese. PubMed PMID: 22214578.

11: Chooi YH, Hong YJ, Cacho RA, Tantillo DJ, Tang Y. A cytochrome P450 serves as an unexpected terpene cyclase during fungal meroterpenoid biosynthesis. J Am Chem Soc. 2013 Nov 13;135(45):16805-8. doi: 10.1021/ja408966t. Epub 2013 Nov 1. PubMed PMID: 24161266; PubMed Central PMCID: PMC3872057.

12: Chooi YH, Wang P, Fang J, Li Y, Wu K, Wang P, Tang Y. Discovery and characterization of a group of fungal polycyclic polyketide prenyltransferases. J Am Chem Soc. 2012 Jun 6;134(22):9428-37. doi: 10.1021/ja3028636. Epub 2012 May 25. PubMed PMID: 22590971; PubMed Central PMCID: PMC3904230.

13: Pi B, Yu D, Dai F, Song X, Zhu C, Li H, Yu Y. A genomics based discovery of secondary metabolite biosynthetic gene clusters in Aspergillus ustus. PLoS One. 2015 Feb 23;10(2):e0116089. doi: 10.1371/journal.pone.0116089. eCollection 2015. PubMed PMID: 25706180; PubMed Central PMCID: PMC4338041.

14: Inokoshi J, Nakamura Y, Hongbin Z, Uchida R, Nonaka K, Masuma R, Tomoda H. Spirohexalines, new inhibitors of bacterial undecaprenyl pyrophosphate synthase, produced by Penicillium brasilianum FKI-3368. J Antibiot (Tokyo). 2013 Jan;66(1):37-41. doi: 10.1038/ja.2012.83. Epub 2012 Nov 21. PubMed PMID: 23168407.

15: de la Rosa P, Jordano R, Medina LM. Influence of low concentrations of an acid preservative on sponge cakes under different storage conditions. J Food Sci. 2009 Mar;74(2):M80-2. doi: 10.1111/j.1750-3841.2009.01059.x. PubMed PMID: 19323762.

16: Liu Y, Mándi A, Li XM, Meng LH, Kurtán T, Wang BG. Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides. Mar Drugs. 2015 Jun 5;13(6):3640-52. doi: 10.3390/md13063640. PubMed PMID: 26058014; PubMed Central PMCID: PMC4483649.

17: Wehner FC, Thiel PG, van Rensburg SJ, Demasius IP. Mutagenicity to Salmonella typhimurium of some Aspergillus and Penicillium mycotoxins. Mutat Res. 1978 Nov;58(2-3):193-203. PubMed PMID: 370570.

18: Li G, Kusari S, Lamshöft M, Schüffler A, Laatsch H, Spiteller M. Antibacterial secondary metabolites from an endophytic fungus, Eupenicillium sp. LG41. J Nat Prod. 2014 Nov 26;77(11):2335-41. doi: 10.1021/np500111w. Epub 2014 Oct 30. PubMed PMID: 25356913.

19: Bladt TT, Dürr C, Knudsen PB, Kildgaard S, Frisvad JC, Gotfredsen CH, Seiffert M, Larsen TO. Bio-activity and dereplication-based discovery of ophiobolins and other fungal secondary metabolites targeting leukemia cells. Molecules. 2013 Nov 26;18(12):14629-50. doi: 10.3390/molecules181214629. PubMed PMID: 24287995.

20: Steyn PS, Jemmali M. Some newly discovered mycotoxins. Ann Nutr Aliment. 1977;31(4-6):651-62. PubMed PMID: 613927.