Ansatrienin A | CAS#82189-03-5 | osteoclastic bone resorption antibiotic inhibitor

MedKoo Cat#: 471198 | Name: Ansatrienin A

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Description:

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

Ansatrienin A is an ansamycin antibiotic inhibitor of osteoclastic bone resorption.

Chemical Structure

Ansatrienin A

CAS#82189-03-5

Theoretical Analysis

MedKoo Cat#: 471198

Name: Ansatrienin A

CAS#: 82189-03-5

Chemical Formula: C36H48N2O8

Exact Mass: 636.3410

Molecular Weight: 636.79

Elemental Analysis: C, 67.90; H, 7.60; N, 4.40; O, 20.10

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 400.00	2 Weeks

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Related CAS #

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Synonym

Ansatrienin A, Mycotrienin I

IUPAC/Chemical Name

N-(cyclohexylcarbonyl)-D-alanine (5R,6E,8E,10E,13S,14R,15R,16Z)-15-hydroxy-5-methoxy-14,16-dimethyl-3,22,24-trioxo-2-azabicyclo[18.3.1]tetracosa-6,8,10,16,20,23-hexaen-13-yl ester

InChi Key

WWUVMHRJRCRFSL-UOZMSBJPSA-N

InChi Code

InChI=1S/C36H48N2O8/c1-23-14-13-17-27-20-28(39)21-30(34(27)42)38-32(40)22-29(45-4)18-11-6-5-7-12-19-31(24(2)33(23)41)46-36(44)25(3)37-35(43)26-15-9-8-10-16-26/h5-7,11-12,14,18,20-21,24-26,29,31,33,41H,8-10,13,15-17,19,22H2,1-4H3,(H,37,43)(H,38,40)/b6-5+,12-7+,18-11+,23-14-/t24-,25+,29-,31-,33-/m0/s1

SMILES Code

C[C@H](C(O[C@H]([C@H](C)[C@@H](O)/C(C)=C\CCC1=C2)C/C=C/C=C/C=C/[C@H](OC)CC(NC(C1=O)=CC2=O)=O)=O)NC(C3CCCCC3)=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 636.79 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

1: Patton SM, Cropp TA, Reynolds KA. A novel delta(3),delta(2)-enoyl-CoA isomerase involved in the biosynthesis of the cyclohexanecarboxylic acid-derived moiety of the polyketide ansatrienin A. Biochemistry. 2000 Jun 27;39(25):7595-604. doi: 10.1021/bi0005714. PMID: 10858310. 2: Reynolds KA, Wang P, Fox KM, Speedie MK, Lam Y, Floss HG. Purification and characterization of a novel enoyl coenzyme A reductase from Streptomyces collinus. J Bacteriol. 1992 Jun;174(12):3850-4. doi: 10.1128/jb.174.12.3850-3854.1992. PMID: 1597409; PMCID: PMC206091. 3: Cropp TA, Wilson DJ, Reynolds KA. Identification of a cyclohexylcarbonyl CoA biosynthetic gene cluster and application in the production of doramectin. Nat Biotechnol. 2000 Sep;18(9):980-3. doi: 10.1038/79479. PMID: 10973220. 4: Moore BS, Floss HG. Biosynthetic studies on the origin of the cyclohexanecarboxylic acid moiety of ansatrienin A and omega-cyclohexyl fatty acids. J Nat Prod. 1994 Mar;57(3):382-6. doi: 10.1021/np50105a008. PMID: 8201312. 5: Chen S, von Bamberg D, Hale V, Breuer M, Hardt B, Müller R, Floss HG, Reynolds KA, Leistner E. Biosynthesis of ansatrienin (mycotrienin) and naphthomycin. Identification and analysis of two separate biosynthetic gene clusters in Streptomyces collinus Tü 1892. Eur J Biochem. 1999 Apr;261(1):98-107. doi: 10.1046/j.1432-1327.1999.00244.x. PMID: 10103039. 6: Wu TS, Duncan J, Tsao SW, Chang CJ, Keller PJ, Floss HG. Biosynthesis of the ansamycin antibiotic ansatrienin (mycotrienin) by Streptomyces collinus. J Nat Prod. 1987 Jan-Feb;50(1):108-18. doi: 10.1021/np50049a015. PMID: 3598593. 7: Yamada Y, Tashiro E, Taketani S, Imoto M, Kataoka T. Mycotrienin II, a translation inhibitor that prevents ICAM-1 expression induced by pro- inflammatory cytokines. J Antibiot (Tokyo). 2011 May;64(5):361-6. doi: 10.1038/ja.2011.23. Epub 2011 Mar 30. PMID: 21448188. 8: Reynolds KA, Wang P, Fox KM, Floss HG. Biosynthesis of ansatrienin by Streptomyces collinus: cell-free transformations of cyclohexene- and cyclohexadienecarboxylic acids. J Antibiot (Tokyo). 1992 Mar;45(3):411-9. doi: 10.7164/antibiotics.45.411. PMID: 1577668. 9: Feuerbach D, Waelchli R, Fehr T, Feyen JH. Mycotrienins. A new class of potent inhibitors of osteoclastic bone resorption. J Biol Chem. 1995 Oct 27;270(43):25949-55. doi: 10.1074/jbc.270.43.25949. PMID: 7592784. 10: Kawamura T, Tashiro E, Yamamoto K, Shindo K, Imoto M. SAR study of a novel triene-ansamycin group compound, quinotrierixin, and related compounds, as inhibitors of ER stress-induced XBP1 activation. J Antibiot (Tokyo). 2008 May;61(5):303-11. doi: 10.1038/ja.2008.43. PMID: 18653996. 11: Sugita M, Natori Y, Sasaki T, Furihata K, Shimazu A, Seto H, Otake N. Studies on mycotrienin antibiotics, a novel class of ansamycins. I. Taxonomy, fermentation, isolation and properties of mycotrienins I and II. J Antibiot (Tokyo). 1982 Nov;35(11):1460-6. doi: 10.7164/antibiotics.35.1460. PMID: 7161184. 12: Sugita M, Sasaki T, Furihata K, Seto H, Otake N. Studies on mycotrienin antibiotics, a novel class of ansamycins. II. Structure elucidation and biosynthesis of mycotrienins I and II. J Antibiot (Tokyo). 1982 Nov;35(11):1467-73. doi: 10.7164/antibiotics.35.1467. PMID: 7161185. 13: Panek JS, Masse CE. Total Synthesis of (+)-Mycotrienol and (+)-Mycotrienin I. J Org Chem. 1997 Nov 28;62(24):8290-8291. doi: 10.1021/jo971793j. PMID: 11671962. 14: Kuwano M, Ikezaki K, Mamizuka K, Komiyama S, Seto H, Otake N, Sugita M, Yamaguchi T, Kishiye T, Fukawa H, et al. Potentiation of mitomycin C, 6-mercaptopurine, bleomycin, cis-diamminedichloroplatinum and 5-fluorouracil by mycotrienins and mycotrienols. Gan. 1983 Oct;74(5):759-66. PMID: 6196249.