Hexacyclinol

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Category Others
Catalog number BBF-00951
CAS
Molecular Weight 416.47
Molecular Formula C23H28O7

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Description

Hexacycline is a natural metabolite of the fungus Panus rudis HKI 0254. It has moderate anti-Gram-positive bacteria activity, 4-40μg/mL can inhibit the production of oxidants by polymorphonuclear neutrophils (PMNL) stimulated by zymosan. It inhibits the growth of L-930 and K 562 cells with IC50 of 1.4μg/mL and 0.4μg/mL, respectively, and the IC50 of HeLa cells is 10μg/mL. It also has an anti-Plasmodium effect, and its IC50 for Plasmodium falciparum is 2.4μg/mL.

Specification

Synonyms (+)-Hexacyclinol
IUPAC Name (1S,2S,6S,8S,9R,10S,11S,12R,13S,15S,17R)-9-hydroxy-2-(2-methoxypropan-2-yl)-17-(2-methylprop-1-enyl)-7,14,18-trioxahexacyclo[10.4.2.01,11.04,10.06,8.013,15]octadec-3-ene-5,16-dione
Canonical SMILES CC(=CC1C23C(C=C4C(C2C(O1)C5C(C3=O)O5)C(C6C(C4=O)O6)O)C(C)(C)OC)C
InChI InChI=1S/C23H28O7/c1-8(2)6-11-23-10(22(3,4)27-5)7-9-12(15(25)18-17(29-18)14(9)24)13(23)16(28-11)19-20(30-19)21(23)26/h6-7,10-13,15-20,25H,1-5H3/t10-,11-,12-,13-,15-,16-,17-,18+,19+,20+,23+/m1/s1
InChI Key PFZFRWWDGXFULQ-NHFKQXEKSA-N

Properties

Appearance Colorless Solid
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 615.5±55.0 °C at 760 mmHg
Melting Point 172-173°C
Density 1.4±0.1 g/cm3

Reference Reading

1. (+)-hexacyclinol
David M Pinkerton, Martin G Banwell, Anthony C Willis Acta Crystallogr Sect E Struct Rep Online. 2010 Jan 13;66(Pt 2):o342-3. doi: 10.1107/S1600536810000620.
A SAMPLE OF THE TITLE COMPOUND [SYSTEMATIC NAME: (1aS,2aS,3S,5aS,6aS,7R,7aS,7bS,8R,8aS,10R)-7-hydr-oxy-3-(1-meth-oxy-1-methyl-ethyl)-10-(2-methyl-1-propen-yl)-1a,5a,6a,7,7a,7b,8,8a-octa-hydro-2H-8,2a-(epoxy-methano)phenanthro[2,3-b:6,7-b']bis-oxirene-2,5(3H)-dione], C(23)H(28)O(7), was generated by enanti-oselective synthesis. There are three mol-ecules of the compound in the crystallographic asymmetric unit. Hydrogen bonding between alcohol H atoms and keto groups of adjacent mol-ecules appears to stabilize the structure. The compound is enanti-omerically pure but the absolute configuration could not be determined directly in this study. Accordingly, the illustrated configuration was assigned on the basis of the nature of the chiral nonracemic precursor used in the synthesis.
2. Recent advances in the structure elucidation of small organic molecules by the LSD software
Bertrand Plainchont, Vicente de Paulo Emerenciano, Jean-Marc Nuzillard Magn Reson Chem. 2013 Aug;51(8):447-53. doi: 10.1002/mrc.3965. Epub 2013 Jun 9.
The LSD software proposes the structures of small organic molecules that fit with structural constraints from 1D and 2D NMR spectroscopy. Its initial design introduced limits that needed to be eliminated to extend its scope and help its users choose the most likely structure among those proposed. The LSD software code has been improved, so that it recognizes a wider set of atom types to build molecules. More flexibility has been given in the interpretation of 2D NMR data, including the automatic detection of very long-range correlations. A program named pyLSD was written to deal with problems in which atom types are ambiguously defined. It also provides a (13)C NMR chemical shift-based solution ranking algorithm. PyLSD was able to propose the correct structure of hexacyclinol, a natural product whose structure determination has been highly controversal. The solution was ranked first within a list of ten structures that were produced by pyLSD from the literature NMR data. The structure of an aporphin natural product was determined by pyLSD, taking advantage of the possibility of handling electrically charged atoms. The structure generation of the insect antifeedant azadirachtin by LSD was reinvestigated by pyLSD, considering that three (13)C resonances did not lead to univocal hybridization states.
3. Chemoenzymatic access to versatile epoxyquinol synthons
David M Pinkerton, Martin G Banwell, Anthony C Willis Org Lett. 2009 Oct 1;11(19):4290-3. doi: 10.1021/ol9016657.
The enantiomerically pure and readily available metabolites 10-12 have been converted over four simple steps into the epoxyquinol derivatives 22-24, respectively. Compounds 23 and 24 or their immediate precursors have been exploited in efficient total syntheses of (-)-bromoxone (ent-1), (-)-epiepoformin (ent-2), (-)-harveynone (4), (+)-panepophenanthrin (6), and (+)-hexacyclinol (9).

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