Cochlioquinone A

For research use only. Not for therapeutic Use.

  • CAT Number: R004545
  • CAS Number: 32450-25-2
  • Molecular Formula: C30H44O8
  • Molecular Weight: 532.674
  • Purity: 99%
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Cochlioquinone A is the major component of a bioactive pigment isolated from Bipolaris leersia. Cochlioquinone A is anti-angiogenic and exhibits inhibitory activity against diacylglycerol acyltransferase and NADH-ubiquinone reductase.<br />
Cochlioquinone A is an antagonist of the human chemokine receptor, CCR5, in HIV-1.


Catalog Number R004545
CAS Number 32450-25-2
Synonyms

(3R,4aR,6aR,12S,12aS,12bR)-9-[(1S,2R,3S)-2-(acetyloxy)-1,3-dimethylpentyl]-1,2,3,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-3-(1-hydroxy-1-methylethyl-6a,12b-dimethyl-pyrano[3,2-a]xanthene-8,11-dione

Molecular Formula C30H44O8
Purity 99%
Target DGK
Appearance Yellow Lyophilisate
Storage -20°C
Analysis method HPLC
IUPAC Name [(2S,3R,4S)-2-[(3R,4aR,6aR,12S,12aS,12bR)-12-hydroxy-3-(2-hydroxypropan-2-yl)-6a,12b-dimethyl-8,11-dioxo-1,2,3,4a,5,6,12,12a-octahydropyrano[3,2-a]xanthen-9-yl]-4-methylhexan-3-yl] acetate
InChI InChI=1S/C30H44O8/c1-9-15(2)25(36-17(4)31)16(3)18-14-19(32)22-24(34)27-29(7)12-10-20(28(5,6)35)37-21(29)11-13-30(27,8)38-26(22)23(18)33/h14-16,20-21,24-25,27,34-35H,9-13H2,1-8H3/t15-,16-,20+,21+,24+,25+,27+,29-,30+/m0/s1
InChIKey UWSYUCZPPVXEKW-MHUJPXPPSA-N
SMILES CCC(C)C(C(C)C1=CC(=O)C2=C(C1=O)OC3(CCC4C(C3C2O)(CCC(O4)C(C)(C)O)C)C)OC(=O)C
Reference

Cochlioquinones and epi-cochlioquinones: antagonists of the human chemokine receptor CCR5 from Bipolaris brizae and Stachybotrys chartarum. Yoganathan K., et al. , J. Antibiot. 2004, 57, 59.&nbsp;<br />
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Cochlioquinone A1, a new anti-angiogenic agent from Bipolaris zeicola. Jung H.J. et al. , Bioorg. Med. Chem. 2003, 11, 4743.&nbsp;<br />
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Inhibitory activity of diacylglycerol acyltransferase by cochlioquinones A and A1. Lee H.B. et al. , J. Antibiot. 2003, 56, 967.&nbsp;<br />
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Phytotoxic compounds cochlioquinones are inhibitors of mitochondrial NADH-ubiquinone reductase. Lim C.-H. et al. , J. Pesticide Sci. 1996, 21, 213.
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