7-Chloro-1-O-methylemodin

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7-Chloro-1-O-methylemodin
Category Enzyme inhibitors
Catalog number BBF-01308
CAS 19267-89-1
Molecular Weight 318.71
Molecular Formula C16H11ClO5

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Description

It is produced by the strain of Fusarium aquaedeductuum WC-5228. It inhibits the binding activity of type B endothelin-1 (ETB) receptor with IC50 of 50 μmol/L. It has antibacterial activities against Gram-positive bacteria, including vancomycin-resistant Enterococcus faecium and methicillin-resistant Staphylococcus aureus.

Specification

Synonyms 7-Chloro-6,8-dihydroxy-1-meth-oxy-3-methylanthraquinone; 1,3-dihydroxy-8-methoxy-2-chloro-6-methylanthraquinone
IUPAC Name 2-chloro-1,3-dihydroxy-8-methoxy-6-methylanthracene-9,10-dione
Canonical SMILES CC1=CC2=C(C(=C1)OC)C(=O)C3=C(C(=C(C=C3C2=O)O)Cl)O
InChI InChI=1S/C16H11ClO5/c1-6-3-7-11(10(4-6)22-2)15(20)12-8(14(7)19)5-9(18)13(17)16(12)21/h3-5,18,21H,1-2H3
InChI Key CLRXTBMRGOWHGZ-UHFFFAOYSA-N

Properties

Appearance Orange Crystal
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 279-281 °C

Reference Reading

1. Antiviral activities of anthraquinones, bianthrones and hypericin derivatives from lichens
P A Cohen, J B Hudson, G H Towers Experientia. 1996 Feb 15;52(2):180-3. doi: 10.1007/BF01923366.
The antiviral activities of some naturally occurring anthraquinones, bianthrones, and hypericin derivatives were compared by the end-point CPE (viral cytopathic effects) method and plaque assays. Under optimal conditions of exposure to light, hypericin, 7,7'-dichlorohypericin and 5,7-dichloroemodin exhibited strong inhibitory activity against HSV-1 (herpes simplex virus type 1) in both assays. Partial inactivation of the virus was shown by emodin, 7-chloroemodin and 7-chloro-1-O-methylemodin; the bianthrones and other anthraquinones were found to be inactive. Antiviral activity appeared to be positively correlated with increasing substitution of chlorine in the anthraquinone structure. In the absence of light, only hypericin and 7,7'-dichlorohypericin displayed detectable activity.

Bio Calculators

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L

* 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

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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