Viridicatumtoxin | CAS#39277-41-3 | Tetracycline antibiotic

MedKoo Cat#: 461859 | Name: Viridicatumtoxin

Featured

Description:

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

Viridicatumtoxin is a fungus-derived tetracycline-like antibiotic.

Chemical Structure

Viridicatumtoxin

CAS#39277-41-3

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

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 1,100.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

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

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 565.57 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.

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: 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.