Basic information
- CAS
151487-20-6- Standard SMILES
Oc1c(Cl)cc(Cl)cc1-c1c(Cl)cc(Cl)c(Oc2ccc(Cl)cc2Cl)c1O- InChIKey
AHLSIYMTIQLHAO-UHFFFAOYSA-N- Molecular formula
- C18H8Cl6O3
- Average molar mass
- 485 g/mol
- Monoisotopic mass
- 481.86046
Overview
Ambigol A is a polychlorobiphenyl.
Names & identifiers
- Preferred name
- Ambigol A
- IUPAC
- 3,5-dichloro-2-(3,5-dichloro-2-hydroxyphenyl)-6-(2,4-dichlorophenoxy)phenol
- English name
- ambigol A
- Molecular formula
- C18H8Cl6O3
- Molecular weight
- 484.97
Names & synonyms
Ambigol A151487-20-63,5-dichloro-2-(3,5-dichloro-2-hydroxyphenyl)-6-(2,4-dichlorophenoxy)phenolDTXSID20164794RefChem:111857DTXCID50872853-(2,4-Dichlorophenoxy)-3',4,5'-,6-tetrachloro-2,2'-biphenyldiolCHEMBL479907SCHEMBL29496176CHEBI:214078GLXC-231193',4,5',6-Tetrachloro-3-(2,4-dichlorophenoxy)[1,1'-biphenyl]-2,2'-diol
Show more names
Aids085791Aids-085791[1,1'-Biphenyl]-2,2'-diol, 3',4,5',6-tetrachloro-3-(2,4-dichlorophenoxy)-
3,5-dichloro-2-(3,5-dichloro-2-hydroxy-phenyl)-6-(2,4-dichlorophenoxy)phenol
Database identifiers
- CAS
151487-20-6- PubChem CID
- 475341
- DTXSID
DTXSID20164794- ChEMBL
CHEMBL479907- ChEBI
CHEBI:214078
Properties
Computed structural properties
- XLogP
- 8.1
- Topological polar surface area
- 49.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 500
Chemistry & industry
Applications
DescriptionAmbigol A is an antibiotic against Serratia sp. ATCC 39006 (S39006) strain. The terrestrial cyanobacterium Fischerella ambigua 108b produces the three polychlorinated triphenyls ambigol A–C that exhibit interesting antimicrobial, antiviral and cytotoxic activities. They are structurally related to polybrominated diphenylethers synthesized by diverse marine bacteria that are known to be highly toxic and are bioaccumulating in natural food webs. All ambigols display unusual connectivities: Ambigols A and B exhibit chlorination and ambigol C biaryl-ether bonds in the relative meta position at the central phenol unit, which is flanked by two 2,4-dichlorophenol units in all three compounds. Here we report on the identification of the biosynthetic gene cluster (BGC) reponsible for ambigol production in F. ambigua.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…