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MedKoo Cat#: 562856 | Name: Chaetominine

Description:

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

Chaetominine is a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015.

Chemical Structure

Chaetominine
Chaetominine
CAS#918659-56-0

Theoretical Analysis

MedKoo Cat#: 562856

Name: Chaetominine

CAS#: 918659-56-0

Chemical Formula: C22H18N4O4

Exact Mass: 402.1328

Molecular Weight: 402.41

Elemental Analysis: C, 65.66; H, 4.51; N, 13.92; O, 15.90

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 #
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Synonym
Chaetominine; NSC-746369; NSC 746369; NSC746369;
IUPAC/Chemical Name
(2S,4R,5aS,9cS)-5a-Hydroxy-2-methyl-4-(4-oxoquinazolin-3(4H)-yl)-4,5,5a,9c-tetrahydro-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione
InChi Key
GEURDGODABUDHB-TYTLQBBQSA-N
InChi Code
InChI=1S/C22H18N4O4/c1-12-18(27)26-16-9-5-3-7-14(16)22(30)10-17(20(29)25(12)21(22)26)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1
SMILES Code
O=C(N1C2=C([C@@]3(O)C[C@H]4N5C=NC6=C(C=CC=C6)C5=O)C=CC=C2)[C@H](C)N([C@]31[H])C4=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 402.41 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: Liu CQ, Pan ZH, An FL, Lu YH. Co-addition Strategy for Enhancement of Chaetominine from Submerged Fermentation of Aspergillus fumigatus CY018. Appl Biochem Biotechnol. 2018 Apr 10. doi: 10.1007/s12010-018-2714-6. [Epub ahead of print] PubMed PMID: 29637396. 2: Zhou Y, Breit B. Rhodium-Catalyzed Asymmetric N-H Functionalization of Quinazolinones with Allenes and Allylic Carbonates: The First Enantioselective Formal Total Synthesis of (-)-Chaetominine. Chemistry. 2017 Dec 22;23(72):18156-18160. doi: 10.1002/chem.201705059. Epub 2017 Dec 5. PubMed PMID: 29105185. 3: Yao J, Wei X, Lu Y. Chaetominine reduces MRP1-mediated drug resistance via inhibiting PI3K/Akt/Nrf2 signaling pathway in K562/Adr human leukemia cells. Biochem Biophys Res Commun. 2016 May 13;473(4):867-873. doi: 10.1016/j.bbrc.2016.03.141. Epub 2016 Mar 30. PubMed PMID: 27038543. 4: Liu C, Jiao R, Yao L, Zhang Y, Lu Y, Tan R. Adsorption characteristics and preparative separation of chaetominine from Aspergillus fumigatus mycelia by macroporous resin. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Mar 15;1015-1016:135-141. doi: 10.1016/j.jchromb.2016.02.027. Epub 2016 Feb 20. PubMed PMID: 26919448. 5: Yao J, Jiao R, Liu C, Zhang Y, Yu W, Lu Y, Tan R. Assessment of the Cytotoxic and Apoptotic Eἀects of Chaetominine in a Human Leukemia Cell Line. Biomol Ther (Seoul). 2016 Mar 1;24(2):147-55. doi: 10.4062/biomolther.2015.093. PubMed PMID: 26902083; PubMed Central PMCID: PMC4774495. 6: Shen L, Zhu L, Luo Q, Li XW, Xi JQ, Kong GM, Song YC. Fumigaclavine I, a new alkaloid isolated from endophyte Aspergillus terreus. Chin J Nat Med. 2015 Dec;13(12):937-41. doi: 10.1016/S1875-5364(15)30101-1. PubMed PMID: 26721713. 7: Xu CP, Luo SP, Wang AE, Huang PQ. Complexity generation by chemical synthesis: a five-step synthesis of (-)-chaetominine from L-tryptophan and its biosynthetic implications. Org Biomol Chem. 2014 May 14;12(18):2859-63. doi: 10.1039/c4ob00314d. PubMed PMID: 24675877. 8: Peng QL, Luo SP, Xia XE, Liu LX, Huang PQ. The four-step total synthesis of (-)-chaetominine. Chem Commun (Camb). 2014 Feb 25;50(16):1986-8. doi: 10.1039/c3cc48833k. PubMed PMID: 24413776. 9: Tréguier B, Roche SP. Double annulative cascade of tryptophan-containing peptides triggered by selectfluor. Org Lett. 2014 Jan 3;16(1):278-81. doi: 10.1021/ol403281t. Epub 2013 Dec 11. PubMed PMID: 24328461. 10: Beaumont S, Pons V, Retailleau P, Dodd RH, Dauban P. Catalytic oxyamidation of indoles. Angew Chem Int Ed Engl. 2010 Feb 22;49(9):1634-7. doi: 10.1002/anie.200906650. PubMed PMID: 20112323. 11: Malgesini B, Forte B, Borghi D, Quartieri F, Gennari C, Papeo G. A straightforward total synthesis of (-)-chaetominine. Chemistry. 2009 Aug 10;15(32):7922-9. doi: 10.1002/chem.200900793. PubMed PMID: 19562787. 12: Toumi M, Couty F, Marrot J, Evano G. Total synthesis of chaetominine. Org Lett. 2008 Nov 6;10(21):5027-30. doi: 10.1021/ol802155n. Epub 2008 Oct 11. PubMed PMID: 18847212. 13: Snider BB, Wu X. Synthesis of (-)-chaetominine. Org Lett. 2007 Nov 8;9(23):4913-5. Epub 2007 Oct 18. PubMed PMID: 17944481; PubMed Central PMCID: PMC2527753. 14: Jiao RH, Xu S, Liu JY, Ge HM, Ding H, Xu C, Zhu HL, Tan RX. Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015. Org Lett. 2006 Dec 7;8(25):5709-12. PubMed PMID: 17134253.

View History

CH-38083

CH-38083