MedKoo Cat#: 584713 | Name: Terpentecin

Description:

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

Terpentecin is isolated from strain MF730-N6 and is active against leukemia L-1210 and Ehrlich ascites carcinoma.

Chemical Structure

Terpentecin
Terpentecin
CAS#100440-25-3

Theoretical Analysis

MedKoo Cat#: 584713

Name: Terpentecin

CAS#: 100440-25-3

Chemical Formula: C20H28O6

Exact Mass: 364.1886

Molecular Weight: 364.44

Elemental Analysis: C, 65.92; H, 7.74; O, 26.34

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
Terpentecin; Antibiotic MF 730N6; MF 730N6
IUPAC/Chemical Name
Oxiraneacetaldehyde, 2-(1-hydroxy-2-(1,2,3,4,4a,7,8,8a-octahydro-3-hydroxy-1,2,4a,5-tetramethyl-4-oxo-1-naphthalenyl)ethyl)-alpha-oxo-, (1-alpha(S*(R*)),2-alpha,3-beta,4a-beta,8a-alpha)-
InChi Key
ISTOHHFNKVUOKP-SHNWCLPJSA-N
InChi Code
InChI=1S/C20H28O6/c1-11-6-5-7-13-18(3,12(2)16(24)17(25)19(11,13)4)8-14(22)20(10-26-20)15(23)9-21/h6,9,12-14,16,22,24H,5,7-8,10H2,1-4H3/t12?,13-,14+,16+,18?,19+,20-/m1/s1
SMILES Code
O=CC([C@@]1([C@@H](O)CC2(C)C(C)[C@H](O)C([C@@]3(C)C(C)=CCC[C@]23[H])=O)OC1)=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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 364.44 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: Kawada S, Yamashita Y, Fujii N, Nakano H. Induction of a heat-stable topoisomerase II-DNA cleavable complex by nonintercalative terpenoides, terpentecin and clerocidin. Cancer Res. 1991 Jun 1;51(11):2922-5. PubMed PMID: 1851667. 2: Tamamura T, Tsuchiya M, Isshiki K, Sawa T, Takeuchi T, Hori M, Sakata N. Terpentecin, an inhibitor of DNA synthesis. J Antibiot (Tokyo). 1988 May;41(5):648-54. PubMed PMID: 3290173. 3: Isshiki K, Tamamura T, Sawa T, Naganawa H, Takeuchi T, Umezawa H. Biosynthetic studies of terpentecin. J Antibiot (Tokyo). 1986 Nov;39(11):1634-5. PubMed PMID: 3793635. 4: Dairi T, Motohira Y, Kuzuyama T, Takahashi S, Itoh N, Seto H. Cloning of the gene encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase from terpenoid antibiotic-producing Streptomyces strains. Mol Gen Genet. 2000 Jan;262(6):957-64. PubMed PMID: 10660057. 5: Hamano Y, Kuzuyama T, Itoh N, Furihata K, Seto H, Dairi T. Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin. J Biol Chem. 2002 Oct 4;277(40):37098-104. Epub 2002 Jul 22. PubMed PMID: 12138123. 6: Arens JC, Haltli B, Kerr RG. Draft Genome Sequence of Kitasatospora griseola Strain MF730-N6, a Bafilomycin, Terpentecin, and Satosporin Producer. Genome Announc. 2015 Mar 26;3(2). pii: e00208-15. doi: 10.1128/genomeA.00208-15. PubMed PMID: 25814608; PubMed Central PMCID: PMC4384148. 7: Kawada S, Yamashita Y, Ochiai K, Ando K, Iwasaki T, Takiguchi T, Nakano H. Terpentecin and ECT4B, new family of topoisomerase II targeting antitumor antibiotics produced by Streptomyces: producing organism, fermentation and large scale purification. J Antibiot (Tokyo). 1995 Mar;48(3):211-6. PubMed PMID: 7730154. 8: Isshiki K, Tamamura T, Takahashi Y, Sawa T, Naganawa H, Takeuchi T, Umezawa H. The structure of a new antibiotic, terpentecin. J Antibiot (Tokyo). 1985 Dec;38(12):1819-21. PubMed PMID: 3841540. 9: Hamano Y, Dairi T, Yamamoto M, Kawasaki T, Kaneda K, Kuzuyama T, Itoh N, Seto H. Cloning of a gene cluster encoding enzymes responsible for the mevalonate pathway from a terpenoid-antibiotic-producing Streptomyces strain. Biosci Biotechnol Biochem. 2001 Jul;65(7):1627-35. PubMed PMID: 11515548. 10: Dairi T, Hamano Y, Kuzuyama T, Itoh N, Furihata K, Seto H. Eubacterial diterpene cyclase genes essential for production of the isoprenoid antibiotic terpentecin. J Bacteriol. 2001 Oct;183(20):6085-94. PubMed PMID: 11567009; PubMed Central PMCID: PMC99688. 11: Tamamura T, Sawa T, Isshiki K, Masuda T, Homma Y, Inuma H, Naganawa H, Hamada M, Takeuchi T, Umezawa H. Isolation and characterization of terpentecin, a new antitumor antibiotic. J Antibiot (Tokyo). 1985 Dec;38(12):1664-9. PubMed PMID: 3841535. 12: Dairi T. Studies on biosynthetic genes and enzymes of isoprenoids produced by actinomycetes. J Antibiot (Tokyo). 2005 Apr;58(4):227-43. Review. PubMed PMID: 15981409. 13: Kawasaki T, Kuzuyama T, Kuwamori Y, Matsuura N, Itoh N, Furihata K, Seto H, Dairi T. Presence of copalyl diphosphate synthase gene in an actinomycete possessing the mevalonate pathway. J Antibiot (Tokyo). 2004 Nov;57(11):739-47. PubMed PMID: 15712669. 14: Hamano Y, Dairi T, Yamamoto M, Kuzuyama T, Itoh N, Seto H. Growth-phase dependent expression of the mevalonate pathway in a terpenoid antibiotic-producing Streptomyces strain. Biosci Biotechnol Biochem. 2002 Apr;66(4):808-19. PubMed PMID: 12036054. 15: Eguchi T, Dekishima Y, Hamano Y, Dairi T, Seto H, Kakinuma K. A new approach for the investigation of isoprenoid biosynthesis featuring pathway switching, deuterium hyperlabeling, and 1H NMR spectroscopy. The reaction mechanism of a novel streptomyces diterpene cyclase. J Org Chem. 2003 Jul 11;68(14):5433-8. PubMed PMID: 12839434. 16: Kawasaki T, Kuzuyama T, Furihata K, Itoh N, Seto H, Dairi T. A relationship between the mevalonate pathway and isoprenoid production in actinomycetes. J Antibiot (Tokyo). 2003 Nov;56(11):957-66. PubMed PMID: 14763562. 17: Nakano H. [Antitumor agents targeting mammalian topoisomerases]. Gan To Kagaku Ryoho. 1991 Aug;18(10):1550-5. Review. Japanese. PubMed PMID: 1651681. 18: Inaba M, Mitsuhashi J, Kawada S, Nakano H. Different modes of cell-killing action between DNA topoisomerase I and II inhibitors revealed by kinetic analysis. Jpn J Cancer Res. 1994 Feb;85(2):187-93. PubMed PMID: 8144400; PubMed Central PMCID: PMC5919418. 19: Kawada SZ, Yamashita Y, Uosaki Y, Gomi K, Iwasaki T, Takiguchi T, Nakano H. UCT4B, a new antitumor antibiotic with topoisomerase II mediated DNA cleavage activity, from Streptomyces sp. J Antibiot (Tokyo). 1992 Jul;45(7):1182-4. PubMed PMID: 1325436. 20: Fujii N, Yamashita Y, Saitoh Y, Nakano H. Induction of mammalian DNA topoisomerase I-mediated DNA cleavage and DNA winding by bulgarein. J Biol Chem. 1993 Jun 25;268(18):13160-5. PubMed PMID: 8390457.