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MedKoo Cat#: 585381 | Name: Viridin

Description:

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

Viridin is an antifungal metabolite of Gliocladium virens that was first reported in 1945.

Chemical Structure

Viridin
Viridin
CAS#3306-52-3

Theoretical Analysis

MedKoo Cat#: 585381

Name: Viridin

CAS#: 3306-52-3

Chemical Formula: C20H16O6

Exact Mass: 352.0947

Molecular Weight: 352.34

Elemental Analysis: C, 68.18; H, 4.58; O, 27.24

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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Related CAS #
No Data
Synonym
Viridin
IUPAC/Chemical Name
(1R,17S,18S)-18-hydroxy-17-methoxy-1-methyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),3,5(9),12(19),14-pentaene-6,11,16-trione
InChi Key
YEIGUXGHHKAURB-VAMGGRTRSA-N
InChi Code
InChI=1S/C20H16O6/c1-20-11-5-3-8-9(4-6-12(8)21)13(11)16(23)17-14(20)10(7-26-17)15(22)18(25-2)19(20)24/h3,5,7,18-19,24H,4,6H2,1-2H3/t18-,19-,20-/m1/s1
SMILES Code
O=C1C(C=CC([C@@]2(C)[C@H](O)[C@H](OC)C3=O)=C4C(C5=C2C3=CO5)=O)=C4CC1
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 352.34 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: Jones RW, Hancock JG. Conversion of viridin to viridiol by viridin-producing fungi. Can J Microbiol. 1987 Nov;33(11):963-6. PubMed PMID: 3447692. 2: Ji Y, Xin Z, He H, Gao S. Total Synthesis of Viridin and Viridiol. J Am Chem Soc. 2019 Oct 16;141(41):16208-16212. doi: 10.1021/jacs.9b08577. Epub 2019 Oct 3. PubMed PMID: 31554399. 3: Del Bel M, Abela AR, Ng JD, Guerrero CA. Enantioselective Chemical Syntheses of the Furanosteroids (-)-Viridin and (-)-Viridiol. J Am Chem Soc. 2017 May 24;139(20):6819-6822. doi: 10.1021/jacs.7b02829. Epub 2017 May 12. PubMed PMID: 28463562. 4: Law DJ, Dajani AS. Interactions between Neisseria sicca and viridin B, a bacteriocin produced by Streptococcus mitis. Antimicrob Agents Chemother. 1978 Mar;13(3):473-8. PubMed PMID: 263887; PubMed Central PMCID: PMC352266. 5: Pollastro F, Caprioglio D, Marotta P, Moriello AS, De Petrocellis L, Taglialatela-Scafati O, Appendino G. Iodine-Promoted Aromatization of p-Menthane-Type Phytocannabinoids. J Nat Prod. 2018 Mar 23;81(3):630-633. doi: 10.1021/acs.jnatprod.7b00946. Epub 2017 Dec 14. PubMed PMID: 29240420. 6: Dajani AS, Veres CM, Law DJ. Substances that interfere with action of viridin B, a Streptococcus mitis bacteriocin. Infect Immun. 1978 Apr;20(1):20-4. PubMed PMID: 669792; PubMed Central PMCID: PMC421543. 7: Andersson PF, Bengtsson S, Cleary M, Stenlid J, Broberg A. Viridin-like steroids from Hymenoscyphus pseudoalbidus. Phytochemistry. 2013 Feb;86:195-200. doi: 10.1016/j.phytochem.2012.09.012. Epub 2012 Oct 22. PubMed PMID: 23098903. 8: Smith A, Blois J, Yuan H, Aikawa E, Ellson C, Figueiredo JL, Weissleder R, Kohler R, Yaffe MB, Cantley LC, Josephson L. The antiproliferative cytostatic effects of a self-activating viridin prodrug. Mol Cancer Ther. 2009 Jun;8(6):1666-75. doi: 10.1158/1535-7163.MCT-08-1012. Epub 2009 Jun 9. PubMed PMID: 19509266; PubMed Central PMCID: PMC2740925. 9: Pakora GA, Mpika J, Kone D, Ducamp M, Kebe I, Nay B, Buisson D. Inhibition of Phytophthora species, agents of cocoa black pod disease, by secondary metabolites of Trichoderma species. Environ Sci Pollut Res Int. 2018 Oct;25(30):29901-29909. doi: 10.1007/s11356-017-0283-9. Epub 2017 Sep 30. PubMed PMID: 28965291. 10: Blois J, Yuan H, Smith A, Pacold ME, Weissleder R, Cantley LC, Josephson L. Slow self-activation enhances the potency of viridin prodrugs. J Med Chem. 2008 Aug 14;51(15):4699-707. doi: 10.1021/jm800374f. Epub 2008 Jul 17. PubMed PMID: 18630894; PubMed Central PMCID: PMC2663427. 11: Lang Y, Souza FE, Xu X, Taylor NJ, Assoud A, Rodrigo R. Pentacyclic furanosteroids: the synthesis of potential kinase inhibitors related to viridin and wortmannolone. J Org Chem. 2009 Aug 7;74(15):5429-39. doi: 10.1021/jo900922q. PubMed PMID: 19572524. 12: Hayward DG, Newbatt Y, Pickard L, Byrne E, Mao G, Burns S, Sahota NK, Workman P, Collins I, Aherne W, Fry AM. Identification by high-throughput screening of viridin analogs as biochemical and cell-based inhibitors of the cell cycle-regulated nek2 kinase. J Biomol Screen. 2010 Sep;15(8):918-927. doi: 10.1177/1087057110376537. Epub 2010 Jul 27. PubMed PMID: 20664067; PubMed Central PMCID: PMC3947748. 13: Hanson JR. The viridin family of steroidal antibiotics. Nat Prod Rep. 1995 Aug;12(4):381-4. Review. PubMed PMID: 7666979. 14: Apelgren LD, Dajani AS. Purification of a streptococcal bacteriocin (viridin B) and its separation from alpha-hemolysin. Antimicrob Agents Chemother. 1979 Mar;15(3):436-9. PubMed PMID: 464570; PubMed Central PMCID: PMC352678. 15: Hao JJ, Geng C, Xie W, Gong Z, Liu WY, Wang E. Isolation and characterization of viridin, a new 65 kDa antifungal protein from the mould Trichoderma viride. Biol Chem. 1999 Oct;380(10):1243-5. PubMed PMID: 10595589. 16: Dajani AS, Law DJ, Bollinger RO, Ecklund PS. Ultrastructural and biochemical alterations effected by viridin B, a bacterocin of alpha-hemolytic streptococci. Infect Immun. 1976 Sep;14(3):776-82. PubMed PMID: 965095; PubMed Central PMCID: PMC420953. 17: Stangenberg L, Ellson C, Cortez-Retamozo V, Ortiz-Lopez A, Yuan H, Blois J, Smith RA, Yaffe MB, Weissleder R, Benoist C, Mathis D, Josephson L, Mahmood U. Abrogation of antibody-induced arthritis in mice by a self-activating viridin prodrug and association with impaired neutrophil and endothelial cell function. Arthritis Rheum. 2009 Aug;60(8):2314-24. doi: 10.1002/art.24704. PubMed PMID: 19644878; PubMed Central PMCID: PMC3080016. 18: Viswanathan K, Ononye SN, Cooper HD, Kyle Hadden M, Anderson AC, Wright DL. Viridin analogs derived from steroidal building blocks. Bioorg Med Chem Lett. 2012 Nov 15;22(22):6919-22. doi: 10.1016/j.bmcl.2012.09.015. Epub 2012 Sep 13. PubMed PMID: 23040731. 19: Wang GQ, Chen GD, Qin SY, Hu D, Awakawa T, Li SY, Lv JM, Wang CX, Yao XS, Abe I, Gao H. Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage. Nat Commun. 2018 May 9;9(1):1838. doi: 10.1038/s41467-018-04298-2. PubMed PMID: 29743477; PubMed Central PMCID: PMC5943271. 20: Onyango EO, Jacobi PA. Synthetic studies on furanosteroids: construction of the viridin core structure via Diels-Alder/retro-Diels-Alder and vinylogous Mukaiyama aldol-type reaction. J Org Chem. 2012 Sep 7;77(17):7411-27. doi: 10.1021/jo301232w. Epub 2012 Aug 16. PubMed PMID: 22849426.

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