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MedKoo Cat#: 585297 | Name: Aquayamycin

Description:

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

Aquayamycin is an anthraquinone derivative and inhibitor of the enzyme tyrosine hydroxylase..

Chemical Structure

Aquayamycin
CAS#26055-63-0

Theoretical Analysis

MedKoo Cat#: 585297

Name: Aquayamycin

CAS#: 26055-63-0

Chemical Formula: C25H26O10

Exact Mass: 486.1526

Molecular Weight: 486.47

Elemental Analysis: C, 61.72; H, 5.39; O, 32.89

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
Aquayamycin
IUPAC/Chemical Name
9-(Tetrahydro-4',5'-dihydroxy-6'-methyl-2'H-pyran-2'-yl)-3,4,4a,12b-tetrahydro-3,4a,8,12b-tetrahydroxy-3-methyl-benz(a)anthracene-1,7,12(2H)-trione
InChi Key
KCOULPRVOZDQEL-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H26O10/c1-10-19(28)14(26)7-15(35-10)11-3-4-12-17(20(11)29)21(30)13-5-6-24(33)9-23(2,32)8-16(27)25(24,34)18(13)22(12)31/h3-6,10,14-15,19,26,28-29,32-34H,7-9H2,1-2H3
SMILES Code
O=C1CC(C)(O)CC2(O)C1(O)C3=C(C(C4=C(C3=O)C=CC(C5CC(O)C(O)C(C)O5)=C4O)=O)C=C2
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 486.47 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: Sezaki M, Kondo S, Maeda K, Umezawa H, Ono M. The structure of aquayamycin. Tetrahedron. 1970 Nov;26(22):5171-90. PubMed PMID: 5499897. 2: Uchida T, Imoto M, Watanabe Y, Miura K, Dobashi T, Matsuda N, Sawa T, Naganawa H, Hamada M, Takeuchi T. Saquayamycins, new aquayamycin-group antibiotics. J Antibiot (Tokyo). 1985 Sep;38(9):1171-81. PubMed PMID: 3840796. 3: Kusumi S, Nakayama H, Kobayashi T, Kuriki H, Matsumoto Y, Takahashi D, Toshima K. Total Synthesis of Aquayamycin. Chemistry. 2016 Dec 23;22(52):18733-18736. doi: 10.1002/chem.201604697. Epub 2016 Nov 18. PubMed PMID: 27859867. 4: Nagatsu T, Ayukawa S, Umezawa H. Inhibition of dopamine beta-hydroxylase by aquayamycin. J Antibiot (Tokyo). 1968 May;21(5):354-7. PubMed PMID: 5726289. 5: Ayukawa S, Takeuchi T, Sezaki M, Hara T, Umezawa H. Inhibition of tyrosine hydroxylase by aquayamycin. J Antibiot (Tokyo). 1968 May;21(5):350-3. PubMed PMID: 5726288. 6: Kirschning A, Chen GW, Dräger G, Schuberth I, Tietze LF. Syntheses and biological evaluation of new glyco-modified angucyclin-antibiotics. Bioorg Med Chem. 2000 Sep;8(9):2347-54. PubMed PMID: 11026547. 7: Nozaki M, Okuno S, Fujisawa H. The mechanism of inhibition of tryptophan 2,3-dioxygenase by aquayamycin. Biochem Biophys Res Commun. 1971 Sep;44(5):1109-16. PubMed PMID: 5160401. 8: Sezaki M, Hara T, Ayukawa S, Takeuchi T, Okami Y. Studies on a new antibiotic pigment, aquayamycin. J Antibiot (Tokyo). 1968 Feb;21(2):91-7. PubMed PMID: 5674372. 9: Rohr J, Thiericke R. Angucycline group antibiotics. Nat Prod Rep. 1992 Apr;9(2):103-37. Review. PubMed PMID: 1620493. 10: Aouiche A, Bijani C, Zitouni A, Mathieu F, Sabaou N. Antimicrobial activity of saquayamycins produced by Streptomyces spp. PAL114 isolated from a Saharan soil. J Mycol Med. 2014 Jun;24(2):e17-23. doi: 10.1016/j.mycmed.2013.09.001. Epub 2013 Oct 16. PubMed PMID: 24139182. 11: Krohn K, Frese P, Flörke U. Biomimetic synthesis of the racemic angucyclinones of the aquayamycin and WP 3688-2 types. Chemistry. 2000 Nov 3;6(21):3887-96. PubMed PMID: 11126949. 12: Trefzer A, Hoffmeister D, Künzel E, Stockert S, Weitnauer G, Westrich L, Rix U, Fuchser J, Bindseil KU, Rohr J, Bechthold A. Function of glycosyltransferase genes involved in urdamycin A biosynthesis. Chem Biol. 2000 Feb;7(2):133-42. PubMed PMID: 10662691. 13: Imamura N, Kakinuma K, Ikekawa N, Tanaka H, Omura S. Biosynthesis of vineomycins A1 and B2. J Antibiot (Tokyo). 1982 May;35(5):602-8. PubMed PMID: 7107524. 14: Drautz H, Zähner H, Rohr J, Zeeck A. Metabolic products of microorganisms. 234. Urdamycins, new angucycline antibiotics from Streptomyces fradiae. I. Isolation, characterization and biological properties. J Antibiot (Tokyo). 1986 Dec;39(12):1657-69. PubMed PMID: 3818439. 15: Kalyon B, Tan GY, Pinto JM, Foo CY, Wiese J, Imhoff JF, Süssmuth RD, Sabaratnam V, Fiedler HP. Langkocyclines: novel angucycline antibiotics from Streptomyces sp. Acta 3034(*). J Antibiot (Tokyo). 2013 Oct;66(10):609-16. doi: 10.1038/ja.2013.53. Epub 2013 Jul 3. PubMed PMID: 23820614. 16: Hayaishi O, Okuno S, Fujisawa H. Inhibition of brain tryptophan 5-monooxygenase by aquayamycin. Biochem Biophys Res Commun. 1970 May 22;39(4):643-50. PubMed PMID: 5490213. 17: Dürr C, Hoffmeister D, Wohlert SE, Ichinose K, Weber M, Von Mulert U, Thorson JS, Bechthold A. The glycosyltransferase UrdGT2 catalyzes both C- and O-glycosidic sugar transfers. Angew Chem Int Ed Engl. 2004 May 24;43(22):2962-5. PubMed PMID: 15170316. 18: Acharya PP, Khatri HR, Janda S, Zhu J. Synthesis and antitumor activities of aquayamycin and analogues of derhodinosylurdamycin A. Org Biomol Chem. 2019 Mar 6;17(10):2691-2704. doi: 10.1039/c9ob00121b. PubMed PMID: 30768092. 19: Hu Z, Qin L, Wang Q, Ding W, Chen Z, Ma Z. Angucycline antibiotics and its derivatives from marine-derived actinomycete Streptomyces sp. A6H. Nat Prod Res. 2016 Nov;30(22):2551-2558. doi: 10.1080/14786419.2015.1120730. Epub 2016 Jan 4. PubMed PMID: 26728112.