Chaetoviridin A | CAS# 128252-98-2 | antifungal

MedKoo Cat#: 412793 | Name: Chaetoviridin A

Description:

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

Chaetoviridin A is an azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a 3-hydroxy-2-methylbutanoyl group at position 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. Isolated from Chaetomium globosum, it exhibits antifungal activity against plant pathogenic fungi.

Chemical Structure

Chaetoviridin A

CAS#128252-98-2

Theoretical Analysis

MedKoo Cat#: 412793

Name: Chaetoviridin A

CAS#: 128252-98-2

Chemical Formula: C23H25ClO6

Exact Mass: 432.1340

Molecular Weight: 432.89

Elemental Analysis: C, 63.81; H, 5.82; Cl, 8.19; O, 22.17

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Chaetoviridin A; ChaetoviridinA; Chaetoviridin-A

IUPAC/Chemical Name

(S)-5-chloro-9-((2S,3R)-3-hydroxy-2-methylbutanoyl)-6a-methyl-3-((S,E)-3-methylpent-1-en-1-yl)-6H-furo[2,3-h]isochromene-6,8(6aH)-dione

InChi Key

HWSQVPGTQUYLEQ-CCBHEJLASA-N

InChi Code

InChI=1S/C23H25ClO6/c1-6-11(2)7-8-14-9-15-16(10-29-14)18-17(20(26)12(3)13(4)25)22(28)30-23(18,5)21(27)19(15)24/h7-13,25H,6H2,1-5H3/b8-7+/t11-,12-,13+,23-/m0/s1

SMILES Code

CC[C@@H](/C=C/C1=CC2=C(C([C@]3(OC(C(C([C@H]([C@H](O)C)C)=O)=C3C2=CO1)=O)C)=O)Cl)C

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

>2 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 432.89 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: Fierro-Cruz JE, Jiménez P, Coy-Barrera E. Fungal endophytes isolated from Protium heptaphyllum and Trattinnickia rhoifolia as antagonists of Fusarium oxysporum. Rev Argent Microbiol. 2017 Jul-Sep;49(3):255-263. doi: 10.1016/j.ram.2016.12.009. Epub 2017 May 8. PMID: 28495036. 2: Yan W, Cao LL, Zhang YY, Zhao R, Zhao SS, Khan B, Ye YH. New Metabolites from Endophytic Fungus Chaetomium globosum CDW7. Molecules. 2018 Nov 4;23(11):2873. doi: 10.3390/molecules23112873. PMID: 30400338; PMCID: PMC6278401. 3: Winter JM, Sato M, Sugimoto S, Chiou G, Garg NK, Tang Y, Watanabe K. Identification and characterization of the chaetoviridin and chaetomugilin gene cluster in Chaetomium globosum reveal dual functions of an iterative highly- reducing polyketide synthase. J Am Chem Soc. 2012 Oct 31;134(43):17900-3. doi: 10.1021/ja3090498. Epub 2012 Oct 19. PMID: 23072467; PMCID: PMC3494086. 4: Sato M, Winter JM, Kishimoto S, Noguchi H, Tang Y, Watanabe K. Combinatorial Generation of Chemical Diversity by Redox Enzymes in Chaetoviridin Biosynthesis. Org Lett. 2016 Mar 18;18(6):1446-9. doi: 10.1021/acs.orglett.6b00380. Epub 2016 Mar 9. PMID: 26959241; PMCID: PMC4903021. 5: Yasukawa K, Takahashi M, Natori S, Kawai K, Yamazaki M, Takeuchi M, Takido M. Azaphilones inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mice. Oncology. 1994 Jan-Feb;51(1):108-12. doi: 10.1159/000227320. PMID: 8265094. 6: Chen GD, Li YJ, Gao H, Chen Y, Li XX, Li J, Guo LD, Cen YZ, Yao XS. New azaphilones and chlorinated phenolic glycosides from Chaetomium elatum with caspase-3 inhibitory activity. Planta Med. 2012 Oct;78(15):1683-9. doi: 10.1055/s-0032-1315211. Epub 2012 Aug 13. PMID: 22890540. 7: Wang W, Liao Y, Chen R, Hou Y, Ke W, Zhang B, Gao M, Shao Z, Chen J, Li F. Chlorinated Azaphilone Pigments with Antimicrobial and Cytotoxic Activities Isolated from the Deep Sea Derived Fungus Chaetomium sp. NA-S01-R1. Mar Drugs. 2018 Feb 13;16(2):61. doi: 10.3390/md16020061. PMID: 29438326; PMCID: PMC5852489. 8: Wang W, Yang J, Liao YY, Cheng G, Chen J, Cheng XD, Qin JJ, Shao Z. Cytotoxic Nitrogenated Azaphilones from the Deep-Sea-Derived Fungus Chaetomium globosum MP4-S01-7. J Nat Prod. 2020 Apr 24;83(4):1157-1166. doi: 10.1021/acs.jnatprod.9b01165. Epub 2020 Mar 20. PMID: 32193933. 9: Tomoda H, Matsushima C, Tabata N, Namatame I, Tanaka H, Bamberger MJ, Arai H, Fukazawa M, Inoue K, Omura S. Structure-specific inhibition of cholesteryl ester transfer protein by azaphilones. J Antibiot (Tokyo). 1999 Feb;52(2):160-70. doi: 10.7164/antibiotics.52.160. PMID: 10344570. 10: Yue HM, Wang M, Gong WF, Zhang LQ. The screening and identification of the biological control fungi Chaetomium spp. against wheat common root rot. FEMS Microbiol Lett. 2018 Nov 1;365(22). doi: 10.1093/femsle/fny242. PMID: 30289449.