Viridicatumtoxin
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MedKoo CAT#: 461859

CAS#: 39277-41-3

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


Chemical Structure

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Viridicatumtoxin
CAS# 39277-41-3

Theoretical Analysis

MedKoo Cat#: 461859
Name: Viridicatumtoxin
CAS#: 39277-41-3
Chemical Formula: C30H31NO10
Exact Mass: 565.19
Molecular Weight: 565.570
Elemental Analysis: C, 63.71; H, 5.52; N, 2.48; O, 28.29

Price and Availability

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5mg USD 970
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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:

Biological target:
In vitro activity:
In vivo activity:

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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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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.

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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.

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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.

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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.

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