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MedKoo Cat#: 573262 | Name: Aranorosin
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Description:

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

Aranorosin is an antibiotic which has been shown to circumvent arbekacin-resistance in MRSA by inhibiting the bifunctional enzyme AAC(6')/APH(2″) and exhibits some anti-cancer activity.

Chemical Structure

Aranorosin
CAS#117184-53-9

Theoretical Analysis

MedKoo Cat#: 573262

Name: Aranorosin

CAS#: 117184-53-9

Chemical Formula: C23H33NO6

Exact Mass: 419.2308

Molecular Weight: 419.52

Elemental Analysis: C, 65.85; H, 7.93; N, 3.34; O, 22.88

Price and Availability

Size Price Availability Quantity
1mg USD 385.00 2 Weeks
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Related CAS #
No Data
Synonym
Aranorosin
IUPAC/Chemical Name
(R,2E,4E)-N-((1'R,2s,3'S,4S,5R,5'R,7'S)-5-hydroxy-6'-oxodihydro-3H-4',8'-dioxaspiro[furan-2,2'-tricyclo[5.1.0.03,5]octan]-4-yl)-4,6-dimethyldodeca-2,4-dienamide
InChi Key
JHTWWPWUODMKEO-ZVNJHPNESA-N
InChi Code
InChI=1S/C23H33NO6/c1-4-5-6-7-8-13(2)11-14(3)9-10-16(25)24-15-12-23(30-22(15)27)20-18(28-20)17(26)19-21(23)29-19/h9-11,13,15,18-22,27H,4-8,12H2,1-3H3,(H,24,25)/b10-9+,14-11+/t13-,15+,18-,19+,20-,21+,22-,23-/m1/s1
SMILES Code
O=C1[C@H]2[C@H](O2)[C@]3(O[C@@H](O)[C@@H](NC(/C=C/C(C)=C/[C@H](C)CCCCCC)=O)C3)[C@H]4[C@@H]1O4
Appearance
Solid powder
Purity
>95% (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 419.52 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: Suga T, Ishii T, Iwatsuki M, Yamamoto T, Nonaka K, Masuma R, Matsui H, Hanaki H, Omura S, Shiomi K. Aranorosin circumvents arbekacin-resistance in MRSA by inhibiting the bifunctional enzyme AAC(6')/APH(2″). J Antibiot (Tokyo). 2012 Oct;65(10):527-9. doi: 10.1038/ja.2012.53. Epub 2012 Jul 4. PMID: 22760297. 2: Nakashima T, Tanaka R, Yamashita Y, Kanda Y, Hara M. Aranorosin and a novel derivative inhibit the anti-apoptotic functions regulated by Bcl-2. Biochem Biophys Res Commun. 2008 Dec 26;377(4):1085-90. doi: 10.1016/j.bbrc.2008.10.112. Epub 2008 Oct 31. PMID: 18977202. 3: Fehlhaber HW, Kogler H, Mukhopadhyay T, Vijayakumar EK, Roy K, Rupp RH, Ganguli BN. Aranorosin, a novel antibiotic from Pseudoarachniotus roseus. II. Structure elucidation. J Antibiot (Tokyo). 1988 Dec;41(12):1785-94. doi: 10.7164/antibiotics.41.1785. PMID: 3209473. 4: Roy K, Mukhopadhyay T, Reddy GC, Desikan KR, Rupp RH, Ganguli BN. Aranorosin, a novel antibiotic from Pseudoarachniotus roseus. I. Taxonomy, fermentation, isolation, chemical and biological properties. J Antibiot (Tokyo). 1988 Dec;41(12):1780-4. doi: 10.7164/antibiotics.41.1780. PMID: 3209472. 5: Tong B, Belcher BP, Nomura DK, Maimone TJ. Chemical investigations into the biosynthesis of the gymnastatin and dankastatin alkaloids. Chem Sci. 2021 May 31;12(25):8884-8891. doi: 10.1039/d1sc02613e. PMID: 34257889; PMCID: PMC8246081. 6: Hammerschmidt L, Aly AH, Abdel-Aziz M, Müller WE, Lin W, Daletos G, Proksch P. Cytotoxic acyl amides from the soil fungus Gymnascella dankaliensis. Bioorg Med Chem. 2015 Feb 15;23(4):712-9. doi: 10.1016/j.bmc.2014.12.068. Epub 2015 Jan 3. PMID: 25600409. 7: Vijayakumar EK, Roy K, Chatterjee S, Mukhopadhyay T, Bhat RG, Ganguli BN. Structure-activity relationships of new aranorosin analogs to antifungal activity. J Antibiot (Tokyo). 1998 May;51(5):522-4. doi: 10.7164/antibiotics.51.522. PMID: 9666184. 8: Roy K, Vijayakumar EK, Mukhopadhyay T, Chatterjee S, Bhat RG, Blumbach J, Ganguli BN. Aranorosinol A and aranorosinol B, two new metabolites from Pseudoarachniotus roseus: production, isolation, structure elucidation and biological properties. J Antibiot (Tokyo). 1992 Oct;45(10):1592-8. doi: 10.7164/antibiotics.45.1592. PMID: 1473986. 9: Wipf P, Jeger P, Kim Y. Thiophilic ring-opening and rearrangement reactions of epoxyketone natural products. Bioorg Med Chem Lett. 1998 Feb 17;8(4):351-6. doi: 10.1016/s0960-894x(98)00026-2. PMID: 9871683.