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MedKoo Cat#: 412784 | Name: Chaetoglobosin D

Description:

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

Chaetoglobosin D is a cytochalasan alkaloid found in Chaetomium globosum and Chaetomium brasiliense. It has a role as an antineoplastic agent

Chemical Structure

Chaetoglobosin D
Chaetoglobosin D
CAS#55945-73-8

Theoretical Analysis

MedKoo Cat#: 412784

Name: Chaetoglobosin D

CAS#: 55945-73-8

Chemical Formula: C32H36N2O5

Exact Mass: 528.2624

Molecular Weight: 528.65

Elemental Analysis: C, 72.70; H, 6.86; N, 5.30; O, 15.13

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
Chaetoglobosin D; ChaetoglobosinD; Chaetoglobosin-D
IUPAC/Chemical Name
(3S,3aR,4S,6S,6aR,7E,10S,11Z,13R,15E,17aR)-3-((1H-indol-3-yl)methyl)-6,13-dihydroxy-4,10,12-trimethyl-5-methylene-2,3,3a,4,5,6,6a,9,10,13-decahydro-1H-cyclotrideca[d]isoindole-1,14,17-trione
InChi Key
FTBNYQWFSWKCKW-MRSLDMDQSA-N
InChi Code
InChI=1S/C32H36N2O5/c1-17-8-7-10-23-30(38)20(4)19(3)28-25(15-21-16-33-24-11-6-5-9-22(21)24)34-31(39)32(23,28)27(36)13-12-26(35)29(37)18(2)14-17/h5-7,9-14,16-17,19,23,25,28-30,33,37-38H,4,8,15H2,1-3H3,(H,34,39)/b10-7+,13-12+,18-14-/t17-,19+,23-,25-,28-,29+,30+,32+/m0/s1
SMILES Code
C[C@H]1C/C=C/[C@H]2[C@@H](C([C@H]([C@H]3[C@@H](NC([C@@]23C(/C=C/C([C@@H](/C(C)=C\1)O)=O)=O)=O)Cc(c[nH]4)c5c4cccc5)C)=C)O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 528.65 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: Jiang C, Song J, Zhang J, Yang Q. New production process of the antifungal chaetoglobosin A using cornstalks. Braz J Microbiol. 2017 Jul-Sep;48(3):410-418. doi: 10.1016/j.bjm.2016.11.008. Epub 2017 Feb 4. PMID: 28223029; PMCID: PMC5498411. 2: Zheng QC, Kong MZ, Zhao Q, Chen GD, Tian HY, Li XX, Guo LD, Li J, Zheng YZ, Gao H. Chaetoglobosin Y, a new cytochalasan from Chaetomium globosum. Fitoterapia. 2014 Mar;93:126-31. doi: 10.1016/j.fitote.2013.12.022. Epub 2014 Jan 11. PMID: 24418656. 3: Zhu X, Zhou D, Liang F, Wu Z, She Z, Li C. Penochalasin K, a new unusual chaetoglobosin from the mangrove endophytic fungus Penicillium chrysogenum V11 and its effective semi-synthesis. Fitoterapia. 2017 Nov;123:23-28. doi: 10.1016/j.fitote.2017.09.016. Epub 2017 Sep 27. PMID: 28958956. 4: Jiang T, Wang M, Li L, Si J, Song B, Zhou C, Yu M, Wang X, Zhang Y, Ding G, Zou Z. Overexpression of the Global Regulator LaeA in Chaetomium globosum Leads to the Biosynthesis of Chaetoglobosin Z. J Nat Prod. 2016 Oct 28;79(10):2487-2494. doi: 10.1021/acs.jnatprod.6b00333. Epub 2016 Oct 19. PMID: 27759375. 5: Maruyama K, Oosawa M, Tashiro A, Suzuki T, Tanikawa M, Kikuchi M, Sekita S, Natori S. Effects of chaetoglobosin J on the G-F transformation of actin. Biochim Biophys Acta. 1986 Nov 21;874(2):137-43. doi: 10.1016/0167-4838(86)90110-x. PMID: 3778915. 6: Wang Z, Cui J, Gao W, Yang Q, Chen L, Yang L, Sun Q, Zhang H. Effects of rice straw structure on chaetoglobosin A production by Chaetomium globosum CGMCC 6882. Int J Biol Macromol. 2020 May 1;150:1223-1228. doi: 10.1016/j.ijbiomac.2019.10.132. Epub 2019 Nov 16. PMID: 31743701. 7: Xue M, Zhang Q, Gao JM, Li H, Tian JM, Pescitelli G. Chaetoglobosin Vb from endophytic Chaetomium globosum: absolute configuration of chaetoglobosins. Chirality. 2012 Aug;24(8):668-74. doi: 10.1002/chir.22068. Epub 2012 May 17. PMID: 22593034. 8: Yang MH, Gu ML, Han C, Guo XJ, Yin GP, Yu P, Kong LY. Aureochaeglobosins A-C, Three [4 + 2] Adducts of Chaetoglobosin and Aureonitol Derivatives from Chaetomium globosum. Org Lett. 2018 Jun 1;20(11):3345-3348. doi: 10.1021/acs.orglett.8b01243. Epub 2018 May 17. PMID: 29771535. 9: Hu Y, Hao X, Chen L, Akhberdi O, Yu X, Liu Y, Zhu X. Gα-cAMP/PKA pathway positively regulates pigmentation, chaetoglobosin A biosynthesis and sexual development in Chaetomium globosum. PLoS One. 2018 Apr 13;13(4):e0195553. doi: 10.1371/journal.pone.0195553. PMID: 29652900; PMCID: PMC5898716. 10: Hu Y, Hao X, Lou J, Zhang P, Pan J, Zhu X. A PKS gene, pks-1, is involved in chaetoglobosin biosynthesis, pigmentation and sporulation in Chaetomium globosum. Sci China Life Sci. 2012 Dec;55(12):1100-8. doi: 10.1007/s11427-012-4409-5. Epub 2012 Dec 12. PMID: 23233225.