Chaetoglobosin A Acetate

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MedKoo CAT#: 464012

CAS#: 50939-69-0

Description: 19-O-Acetylchaetoglobosin A (Chaetoglobosin A Acetate) is a fungal metabolite originally isolated from C. globosum that has actin polymerization inhibitory and cytotoxic activities. It inhibits actin polymerization in a cell-free assay when used at a concentration of 2 µM. 19-O-Acetylchaetoglobosin A is cytotoxic to HeLa cervical cancer cells.

Chemical Structure

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Chaetoglobosin A Acetate
CAS# 50939-69-0
Instruction

Theoretical Analysis

MedKoo Cat#: 464012
Name: Chaetoglobosin A Acetate
CAS#: 50939-69-0
Chemical Formula: C34H38N2O6
Exact Mass: 570.27
Molecular Weight: 570.686
Elemental Analysis: C, 71.56; H, 6.71; N, 4.91; O, 16.82

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Chaetoglobosin A Acetate; Chaetoglobosin A-Acetate; Chaetoglobosin-A Acetate; Chaetoglobosin-A-Acetate; 19-O-Acetylchaetoglobosin A;

IUPAC/Chemical Name: (1E,4S,5E,7R,9E,11aR,14S,14aR,15S,15aR,16aS,16bR)-14-((1H-indol-3-yl)methyl)-4,6,15,15a-tetramethyl-8,11,12-trioxo-4,7,8,11,12,13,14,14a,15,15a,16a,16b-dodecahydro-3H-cyclotrideca[d]oxireno[2,3-f]isoindol-7-yl acetate

InChi Key: AZLAYOMQTNEYFJ-YZYWEBORSA-N

InChi Code: InChI=1S/C34H38N2O6/c1-18-9-8-11-24-31-33(5,42-31)20(3)29-26(16-22-17-35-25-12-7-6-10-23(22)25)36-32(40)34(24,29)28(39)14-13-27(38)30(19(2)15-18)41-21(4)37/h6-8,10-15,17-18,20,24,26,29-31,35H,9,16H2,1-5H3,(H,36,40)/b11-8+,14-13+,19-15+/t18-,20-,24-,26-,29-,30+,31-,33+,34+/m0/s1

SMILES Code: [H][C@@]1([C@@]2(O[C@]2(C)[C@@H](C)[C@@]3([H])[C@H](CC4=CNC5=C4C=CC=C5)NC([C@]31C(/C=C/C([C@@H]6OC(C)=O)=O)=O)=O)[H])/C=C/C[C@@H](/C=C6\C)C

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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 570.69 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: Ashrafi S, Helaly S, Schroers HJ, Stadler M, Richert-Poeggeler KR, Dababat AA, Maier W. Ijuhya vitellina sp. nov., a novel source for chaetoglobosin A, is a destructive parasite of the cereal cyst nematode Heterodera filipjevi. PLoS One. 2017 Jul 12;12(7):e0180032. doi: 10.1371/journal.pone.0180032. PMID: 28700638; PMCID: PMC5507501.

2: Ratnayake R, Fremlin LJ, Lacey E, Gill JH, Capon RJ. Acremolides A-D, lipodepsipeptides from an Australian marine-derived fungus, Acremonium sp. J Nat Prod. 2008 Mar;71(3):403-8. doi: 10.1021/np070589g. Epub 2008 Feb 21. PMID: 18288804.

3: Von Wallbrunn C, Luftmann H, Bergander K, Meinhardt F. Phytotoxic chaetoglobosins are produced by the plant pathogen Calonectria morganii (anamorph Cylindrocladium scoparium). J Gen Appl Microbiol. 2001 Feb;47(1):33-38. doi: 10.2323/jgam.47.33. PMID: 12483566.

4: Bogyo D, Vaidya N, Flashner M, Tanenbaum SW. Photoaffinity labeling of plasma membrane receptors for cytochalasins in Ehrlich tumor cells. Biochimie. 1988 Feb;70(2):187-91. doi: 10.1016/0300-9084(88)90060-0. PMID: 3134942.