Venturicidin A | CAS# 33538-72-5 | Antibiotic

MedKoo Cat#: 571281 | Name: Venturicidin A

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Description:

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

Venturicidin A is a macrolide antibiotic that acts as a potent inhibitor of mitochondrial and bacterial ATP synthase (F₁F₀-ATPase). By binding to the F₀ subunit of ATP synthase, it disrupts ATP production, leading to impaired cellular energy metabolism. This mechanism makes Venturicidin A a valuable tool in research on oxidative phosphorylation and bioenergetics.

Chemical Structure

Venturicidin A

CAS#33538-71-5

Theoretical Analysis

MedKoo Cat#: 571281

Name: Venturicidin A

CAS#: 33538-71-5

Chemical Formula: C41H67NO11

Exact Mass: 749.4714

Molecular Weight: 749.98

Elemental Analysis: C, 65.66; H, 9.01; N, 1.87; O, 23.47

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450.00	2 Weeks
5mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Venturicidin A; A-130; A130; A 130; AA 0368; AA-0368; AA0368

IUPAC/Chemical Name

(2R,3R,4R,6R)-3-hydroxy-6-(((1R,5S,6R,8R,9E,11R,15Z,17R)-1-hydroxy-5-((2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl)-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl)oxy)-2-methyltetrahydro-2H-pyran-4-yl carbamate

InChi Key

HHQKNFDAEDTRJK-KXQVSFSQSA-N

InChi Code

InChI=1S/C41H67NO11/c1-10-32(43)29(8)36(45)26(5)20-28(7)38-27(6)19-23(2)15-16-31(50-35-21-33(51-40(42)47)37(46)30(9)49-35)14-12-11-13-24(3)39-25(4)17-18-41(48,53-39)22-34(44)52-38/h13,15-17,23,26-31,33,35-39,45-46,48H,10-12,14,18-22H2,1-9H3,(H2,42,47)/b16-15+,24-13-/t23-,26+,27+,28+,29+,30+,31+,33+,35-,36-,37+,38-,39+,41+/m0/s1

SMILES Code

CCC([C@H]([C@H]([C@@H](C[C@H]([C@H]1OC(C[C@]2(CC=C([C@@H](/C(C)=C\CCC[C@H](/C=C/[C@@H](C[C@H]1C)C)O[C@H]3C[C@H]([C@@H]([C@H](O3)C)O)OC(N)=O)O2)C)O)=O)C)C)O)C)=O

Appearance

Solid powder

Purity

>95% (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 749.98 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

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Inhibitors of ATP Synthase as New Antibacterial Candidates. Antibiotics (Basel). 2023 Mar 24;12(4):650. doi: 10.3390/antibiotics12040650. PMID: 37107012; PMCID: PMC10135114. 5: Rao DF, Zhang H, Wang JL, Meng XX, Li ZZ, Xie CY, Jaidi IE, Dai L, Ye JJ, Zhu M, Peng YJ, Chen Q, Zhang DX, Teng YB. Structural insights into the substrate binding sites of O-carbamoyltransferase VtdB from Streptomyces sp. NO1W98. Biochem Biophys Res Commun. 2023 Jun 4;659:40-45. doi: 10.1016/j.bbrc.2023.03.081. Epub 2023 Mar 31. PMID: 37031593. 6: Zharova TV, Kozlovsky VS, Grivennikova VG. Interaction of Venturicidin and Fo·F1-ATPase/ATP Synthase of Tightly Coupled Subbacterial Particles of Paracoccus denitrificans in Energized Membranes. Biochemistry (Mosc). 2022 Aug;87(8):742-751. doi: 10.1134/S0006297922080065. PMID: 36171655. 7: Li H, Zhang M, Li H, Yu H, Chen S, Wu W, Sun P. Discovery of Venturicidin Congeners and Identification of the Biosynthetic Gene Cluster from Streptomyces sp. NRRL S-4. J Nat Prod. 2021 Jan 22;84(1):110-119. doi: 10.1021/acs.jnatprod.0c01177. Epub 2020 Dec 23. PMID: 33356258. 8: Yarlagadda V, Medina R, Wright GD. Venturicidin A, A Membrane-active Natural Product Inhibitor of ATP synthase Potentiates Aminoglycoside Antibiotics. Sci Rep. 2020 May 18;10(1):8134. doi: 10.1038/s41598-020-64756-0. PMID: 32424122; PMCID: PMC7235042. 9: Lin J, Weixler D, Daboss S, Seibold GM, Andronescu C, Schuhmann W, Kranz C. Time-resolved ATP measurements during vesicle respiration. Talanta. 2019 Dec 1;205:120083. doi: 10.1016/j.talanta.2019.06.083. Epub 2019 Jun 29. PMID: 31450430. 10: Otoguro K, Ishiyama A, Namatame M, Nishihara A, Furusawa T, Masuma R, Shiomi K, Takahashi Y, Yamada H, Omura S. Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites. J Antibiot (Tokyo). 2008 Jun;61(6):372-8. doi: 10.1038/ja.2008.52. PMID: 18667785. 11: Fourati-Ben Fguira L, Smaoui S, Karray-Rebai I, Bejar S, Mellouli L. The antifungal activity of the terrestrial Streptomyces US80 strain is induced by heat-killed fungi. Biotechnol J. 2008 Aug;3(8):1058-66. doi: 10.1002/biot.200700155. PMID: 18481262. 12: Fourati-Ben Fguira L, Fotso S, Ben Ameur-Mehdi R, Mellouli L, Laatsch H. Purification and structure elucidation of antifungal and antibacterial activities of newly isolated Streptomyces sp. strain US80. Res Microbiol. 2005 Apr;156(3):341-7. doi: 10.1016/j.resmic.2004.10.006. Epub 2004 Dec 15. PMID: 15808937. 13: Evron Y, Pick U. Modification of Sulfhydryl Groups in the [gamma]-Subunit of Chloroplast-Coupling Factor 1 Affects the Proton Slip through the ATP Synthase. Plant Physiol. 1997 Dec;115(4):1549-1555. doi: 10.1104/pp.115.4.1549. PMID: 12223880; PMCID: PMC158621. 14: Galmiche JM, Pezennec S, Zhao R, Girault G, Baeuerlein E. The prokaryotic thermophilic TF1-ATPase is functionally compatible with the eukaryotic CFo-part of the chloroplast ATP-synthase. FEBS Lett. 1994 Jan 31;338(2):152-6. doi: 10.1016/0014-5793(94)80354-4. PMID: 8307173. 15: Valerio M, de Kouchkovsky Y, Haraux F. An attempt to discriminate catalytic and regulatory proton binding sites in membrane-bound, thiol-reduced chloroplast ATPase. Biochemistry. 1992 May 5;31(17):4239-47. doi: 10.1021/bi00132a013. PMID: 1314660. 16: Akita H. [The use of microbial and enzymatic function in organic synthesis. Total synthesis of the aglycone of venturicidins A and B]. Yakugaku Zasshi. 1990 Nov;110(11):789-806. Japanese. doi: 10.1248/yakushi1947.110.11_789. PMID: 2082010. 17: Akita H, Yamada H, Oishi T, Yamaguchi I. Identity of aabomycin A with venturicidins. Agric Biol Chem. 1990 Sep;54(9):2465-6. PMID: 1368582. 18: Gogoll A, Tanner D. Complete 1 H and 13 C NMR spectral assignment of venturicidin A by 2D NMR spectroscopy. Magn Reson Chem. 1989 Sep;27(9):863-871. doi: 10.1002/mrc.1260270909. PMID: 34034427. 19: Ooi BG, Novitski CE, Nagley P. DNA sequence analysis of the oli1 gene reveals amino acid changes in mitochondrial ATPase subunit 9 from oligomycin- resistant mutants of Saccharomyces cerevisiae. Eur J Biochem. 1985 Nov 4;152(3):709-14. doi: 10.1111/j.1432-1033.1985.tb09251.x. PMID: 2932333. 20: Brufani M, Cellai L, Musu C, Keller-Schierlein W. 229. Stoffwechselprodukte von Mikroorganismen. 102. Uber die Struktur der Venturicidine A und [229. Metabolic products of microorganisms. 102. The structure of venturicidin A and B]. Helv Chim Acta. 1972;55(7):2329-46. German. doi: 10.1002/hlca.19720550706. PMID: 4637271.