Hibarimicin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00953 |
| CAS | |
| Molecular Weight | 1725.77 |
| Molecular Formula | C85H112O37 |
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Description
Hibarimicin A is a tyrosine kinase inhibitor produced by Microbispora rosea subsp. hibaria. It selectively inhibits the activity of src tyrosine kinase without affecting protein kinase A and C. It also has moderate anti-Gram-positive bacteria activity with a MIC of 0.8-12.56 μg/mL.
Specification
| IUPAC Name | 5-[(2S,5S,6R)-5-[(2R,6R)-5-acetyl-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-15-[9-[(2S,5S,6R)-5-[(2S,5R,6R)-5-acetyl-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-7-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1,8,10,10a,12-pentahydroxy-3,4-dimethoxy-11-oxo-10-propyl-6a,7,8,9-tetrahydro-6H-tetracen-2-yl]-7-[(4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6,9,12,19-tetrahydroxy-16-methoxy-4-propyl-3-oxapentacyclo[9.8.0.02,8.04,9.013,18]nonadeca-1(11),12,15,18-tetraene-10,14,17-trione |
| Canonical SMILES | CCCC1(C(C(C(C2C1(C(=O)C3=C(C4=C(C=C3C2)C(=C(C(=C4O)C5=C(C(=O)C6=C(C7=C(C(=C6C5=O)O)C(=O)C8(C9C7OC8(C(C(C9OC1CC(C(C(O1)C)O)O)O)OC1CCC(C(O1)C)OC1CCC(C(O1)C)(C(=O)C)O)CCC)O)O)OC)OC)OC)O)O)OC1CC(C(C(O1)C)O)O)O)OC1CCC(C(O1)C)OC1CCC(C(O1)C)(C(=O)C)O)O |
| InChI | InChI=1S/C85H112O37/c1-14-22-82(104)78(120-45-18-16-43(30(3)110-45)116-47-20-24-80(102,34(7)86)36(9)114-47)68(98)71(118-49-28-41(88)60(90)32(5)112-49)40-27-38-26-39-52(62(92)51(38)76(100)84(40,82)105)63(93)56(74(109-13)70(39)107-11)55-64(94)53-54(67(97)73(55)108-12)65(95)57-58(66(53)96)77(101)85(106)59-72(57)122-83(85,23-15-2)79(69(99)75(59)119-50-29-42(89)61(91)33(6)113-50)121-46-19-17-44(31(4)111-46)117-48-21-25-81(103,35(8)87)37(10)115-48/h26,30-33,36-37,40-50,59-61,68-69,71-72,75,78-79,88-93,95-96,98-99,102-106H,14-25,27-29H2,1-13H3/t30-,31-,32+,33+,36-,37-,40?,41-,42-,43+,44+,45+,46+,47-,48+,49+,50?,59?,60+,61+,68?,69?,71?,72?,75?,78?,79?,80+,81?,82?,83?,84?,85?/m1/s1 |
| InChI Key | XGHSXRXEPCUHTN-HTMXLIDQSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >200°C |
Reference Reading
1. Studies on a biomimetic oxidative dimerization approach to the hibarimicins
Ian M Romaine, Gary A Sulikowski Tetrahedron Lett. 2015 Jun 3;56(23):3617-3619. doi: 10.1016/j.tetlet.2015.01.127.
Nature utilizes dimerization as a method of producing structurally complex metabolites. The microbial metabolites known collectively as the hibarimicins are one example of complex natural products produced biosynthetically by dimerization of a phenolic aromatic polyketide. Described in this communication are model studies aimed at demonstrating regiocontrolled oxidative dimerization of phenolic ring systems related to the biosynthetic precursor of the hibarimicin family of natural products.
2. Assignment and stereocontrol of hibarimicin atropoisomers
Ian M Romaine, Jonathan E Hempel, Ganesh Shanmugam, Hiroshi Hori, Yasuhiro Igarashi, Prasad L Polavarapu, Gary A Sulikowski Org Lett. 2011 Sep 2;13(17):4538-41. doi: 10.1021/ol2017005. Epub 2011 Aug 3.
A stereochemical feature of the hibarimicins is a central biaryl (HMP-Y6) or aryl-quinone (hibarimicinone) incorporated as a single atropodiastereomer. Herein, a chiral resolution and deracemization process to access optically enriched biaryls aR-3 and aS-3 is described. From these atropoenantiomers the BCD-EFG ring system of HMP-Y6 is constructed [(+)-aR-7]. Comparison of CD spectra of aR-7 to HMP-Y6 leads to the assignment of HMP-Y6 and hibarimicin B atropoisomers as aR and aS, respectively.
3. Synthetic studies directed toward the AB decalin common to HMP-Y1 and hibarimicinone
Jonathan E Hempel, Darren W Engers, Gary A Sulikowski Tetrahedron Lett. 2014 Mar 26;55(13):2157-2159. doi: 10.1016/j.tetlet.2014.02.069. Epub 2014 Feb 26.
Efforts toward the synthesis of the decalin ring system common to the hibarimicin shunt metabolite HMP-Y1 and parent aglycone hibarimicinone are reported herein. An intramolecular Diels-Alder cyclization rapidly generated the decalin framework. Two approaches toward completion of the AB decalin were vetted. Incorporation of a phenylsulfonyl leaving group β- to both a ketone and a γ-lactone followed by base-induced elimination of sulfinate led to the undesired α,β-unsaturated lactone. Methanolysis of the γ-lactone followed by elimination produced the unexpected bridged cyclic ether by way of an intramolecular oxy-Michael addition of the endo oriented C13 alcohol.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
