Basic Description

Synonyms	Reveromycin A \| 134615-37-5 \| (2E,4S,5S,6E,8E)-10-[(2S,3R,6S,8R,9S)-3-butyl-2-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dienyl]-3-(3-carboxypropanoyloxy)-9-methyl-1,7-dioxaspiro[5.5]undecan-8-yl]-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid \| (2E,4S,5S,6E,8E)-10-[(
Specifications & Purity	solid
Storage Temp	Store at -20°C
Shipped In	Ice chest + Ice pads

Associated Targets(non-human)

ileS Isoleucyl-tRNA synthetase (49 Activities)

Discover Target: ileS

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NRK (373 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Names and Identifiers

IUPAC Name	(2E,4S,5S,6E,8E)-10-[(2S,3R,6S,8R,9S)-3-butyl-2-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dienyl]-3-(3-carboxypropanoyloxy)-9-methyl-1,7-dioxaspiro[5.5]undecan-8-yl]-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid
INCHI	InChI=1S/C36H52O11/c1-6-7-19-35(47-34(44)17-16-32(40)41)21-22-36(46-30(35)14-10-25(3)23-33(42)43)20-18-27(5)29(45-36)13-9-24(2)8-12-28(37)26(4)11-15-31(38)39/h8-12,14-15,23,26-30,37H,6-7,13,16-22H2,1-5H3,(H,38,39)(H,40,41)(H,42,43)/b12-8+,14-10+,15-11+,24-9+,25-23+/t26-,27-,28-,29+,30-,35+,36-/m0/s1
InChi Key	ZESGNAJSBDILTB-OXVOKJAASA-N
Canonical SMILES	CCCCC1(CCC2(CCC(C(O2)CC=C(C)C=CC(C(C)C=CC(=O)O)O)C)OC1C=CC(=CC(=O)O)C)OC(=O)CCC(=O)O
Isomeric SMILES	CCCC[C@]1(CC[C@]2(CC[C@@H]([C@H](O2)C/C=C(\C)/C=C/[C@@H]([C@@H](C)/C=C/C(=O)O)O)C)O[C@H]1/C=C/C(=C/C(=O)O)/C)OC(=O)CCC(=O)O
PubChem CID	9939559
Molecular Weight	660.79

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Solubility	DMF: soluble; DMSO: soluble; ethanol: soluble; ethyl acetate: soluble; methanol: solublesoluble

References

1. H Koshino,H Takahashi,H Osada,K Isono. (1992-09-01) Reveromycins, new inhibitors of eukaryotic cell growth. III. Structures of reveromycins A, B, C and D.. The Journal of antibiotics, 45 ((9)): (1420-1427). [PMID:1429227]
2. K E Drouet,T Ling,H V Tran,E A Theodorakis. (2000-05-18) Enantioselective synthesis of the [6,6] spiroketal core of reveromycin A.. Organic letters, 2 ((2)): (207-210). [PMID:10814283]
3. T Shimizu,T Masuda,K Hiramoto,T Nakata. (2000-07-13) Total synthesis of reveromycin A.. Organic letters, 2 ((14)): (2153-2156). [PMID:10891254]
4. Takeshi Shimizu,Takeo Usui,Kiyotaka Machida,Kouichi Furuya,Hiroyuki Osada,Tadashi Nakata. (2002-11-07) Chemical modification of reveromycin A and its biological activities.. Bioorganic & medicinal chemistry letters, 12 ((23)): (3363-3366). [PMID:12419362]
5. Hiroyuki Osada. (2003-04-08) Development and application of bioprobes for Mammalian cell cycle analyses.. Current medicinal chemistry, 10 ((9)): (727-732). [PMID:12678775]
6. Naoyuki Takahashi,Sadakazu Ejiri,Shigeru Yanagisawa,Hidehiro Ozawa. (2007-07-31) Regulation of osteoclast polarization.. Odontology, 95 ((1)): (1-9). [PMID:17660975]
7. Saburo Sone,Seiji Yano. (2007-09-06) Molecular pathogenesis and its therapeutic modalities of lung cancer metastasis to bone.. Cancer metastasis reviews, 26 ((3-4)): (685-689). [PMID:17786536]
8. Tokichi Miyakawa,Yoshifumi Kobayashi,Masaki Mizunuma. (2007-12-07) [Identification of target molecules for small-molecule inhibitors using yeast].. Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme, 52 ((13 Suppl)): (1719-1723). [PMID:18051406]
9. Je-Tae Woo,Takayuki Yonezawa,Byung-Yoon Cha,Toshiaki Teruya,Kazuo Nagai. (2008-04-24) Pharmacological topics of bone metabolism: antiresorptive microbial compounds that inhibit osteoclast differentiation, function, and survival.. Journal of pharmacological sciences, 106 ((4)): (547-554). [PMID:18431038]
10. Koji Hiraoka,Michihisa Zenmyo,Kousuke Watari,Haruo Iguchi,Abbas Fotovati,Yusuke N Kimura,Fumihito Hosoi,Takanori Shoda,Kensei Nagata,Hiroyuki Osada,Mayumi Ono,Michihiko Kuwano. (2008-08-30) Inhibition of bone and muscle metastases of lung cancer cells by a decrease in the number of monocytes/macrophages.. Cancer science, 99 ((8)): (1595-1602). [PMID:18754872]
11. Makoto Kawatani,Hiroyuki Osada. (2009-08-14) Osteoclast-targeting small molecules for the treatment of neoplastic bone metastases.. Cancer science, 100 ((11)): (1999-2005). [PMID:19673888]
12. Shunji Takahashi,Atsushi Toyoda,Yasuyo Sekiyama,Hiroshi Takagi,Toshihiko Nogawa,Masakazu Uramoto,Ryuichiro Suzuki,Hiroyuki Koshino,Takuto Kumano,Suresh Panthee,Tohru Dairi,Jun Ishikawa,Haruo Ikeda,Yoshiyuki Sakaki,Hiroyuki Osada. (2011-06-07) Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation.. Nature chemical biology, 7 ((7)): (461-468). [PMID:21642985]
13. Kira J Weissman. (2011-06-21) Biosynthesis: a twist in the tail.. Nature chemical biology, 7 ((7)): (409-411). [PMID:21685883]
14. Takahiro Yabumoto,Ken Miyazawa,Masako Tabuchi,Satsuki Shoji,Miyuki Tanaka,Manami Kadota,Mamoru Yoshizako,Makoto Kawatani,Hiroyuki Osada,Hatsuhiko Maeda,Shigemi Goto. (2013-09-03) Stabilization of tooth movement by administration of reveromycin A to osteoprotegerin-deficient knockout mice.. American journal of orthodontics and dentofacial orthopedics : official publication of the American Association of Orthodontists, its constituent societies, and the American Board of Orthodontics, 144 ((3)): (368-380). [PMID:23992809]
15. Z Cui,D Hirata,E Tsuchiya,H Osada,T Miyakawa. (1996-06-21) The multidrug resistance-associated protein (MRP) subfamily (Yrs1/Yor1) of Saccharomyces cerevisiae is important for the tolerance to a broad range of organic anions.. The Journal of biological chemistry, 271 ((25)): (14712-14716). [PMID:8663018]
16. H Takahashi,Y Yamashita,H Takaoka,J Nakamura,M Yoshihama,H Osada. (1997-01-01) Inhibitory action of reveromycin A on TGF-alpha-dependent growth of ovarian carcinoma BG-1 in vitro and in vivo.. Oncology research, 9 ((1)): (7-11). [PMID:9112255]
17. Z Cui,T Shiraki,D Hirata,T Miyakawa. (1998-10-10) Yeast gene YRR1, which is required for resistance to 4-nitroquinoline N-oxide, mediates transcriptional activation of the multidrug resistance transporter gene SNQ2.. Molecular microbiology, 29 ((5)): (1307-1315). [PMID:9767597]
18. Mariana El Sous,Danny Ganame,Peter A Tregloan,Mark A Rizzacasa. (2004-08-28) Total synthesis of (-)-reveromycin a.. Organic letters, 6 ((17)): (3001-3004). [PMID:15330668]
19. Hiroaki Muguruma,Seiji Yano,Soji Kakiuchi,Hisanori Uehara,Makoto Kawatani,Hiroyuki Osada,Saburo Sone. (2005-12-20) Reveromycin A inhibits osteolytic bone metastasis of small-cell lung cancer cells, SBC-5, through an antiosteoclastic activity.. Clinical cancer research : an official journal of the American Association for Cancer Research, 11 ((24 Pt 1)): (8822-8828). [PMID:16361571]
20. Je-Tae Woo,Makoto Kawatani,Masanori Kato,Toshimasa Shinki,Takayuki Yonezawa,Naoki Kanoh,Hiroshi Nakagawa,Masamichi Takami,Kun Hyung Lee,Paula H Stern,Kazuo Nagai,Hiroyuki Osada. (2006-03-16) Reveromycin A, an agent for osteoporosis, inhibits bone resorption by inducing apoptosis specifically in osteoclasts.. Proceedings of the National Academy of Sciences of the United States of America, 103 ((12)): (4729-4734). [PMID:16537392]
21. Russell T Hill. (2006-10-04) Industrial microbiology and biotechnology - 2006 Annual Meeting.. IDrugs : the investigational drugs journal, 9 ((10)): (690-692). [PMID:17016773]
22. Takeshi Shimizu,Takeo Usui,Makoto Fujikura,Makoto Kawatani,Tomoharu Satoh,Kiyotaka Machida,Naoki Kanoh,Je-Tae Woo,Hiroyuki Osada,Mikiko Sodeoka. (2008-06-04) Synthesis and biological activities of reveromycin A and spirofungin A derivatives.. Bioorganic & medicinal chemistry letters, 18 ((13)): (3756-3760). [PMID:18519164]
23. M Tanaka,K Miyazawa,M Tabuchi,T Yabumoto,M Kadota,M Yoshizako,C Yamane,M Kawatani,H Osada,H Maeda,S Goto. (2012-06-08) Effect of Reveromycin A on experimental tooth movement in OPG-/- mice.. Journal of dental research, 91 ((8)): (771-776). [PMID:22674934]
24. Toshihiko Nogawa,Shunji Takahashi,Yasuyo Sekiyama,Hiroshi Takagi,Masakazu Uramoto,Hiroyuki Koshino,Makoto Kawatani,Takeshi Shimizu,Hiroyuki Osada. (2012-12-13) Creation of novel reveromycin derivatives by alcohol-added fermentation.. The Journal of antibiotics, 66 ((4)): (247-250). [PMID:23232929]

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Reveromycin A - solid, high purity , CAS No.134615-37-5