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Tropodithietic acid

CAT: 0804-HY-N6705Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N6705Size:1 mg
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Description
Tropodithietic acid is a sulfur-containing antibiotic produced by the marine bacterium Phaeobacter inhibens. Tropodithietic acid exhibits a strong antibiotic activity against a broad spectrum of bacteria including alpha- and gammaproteobacteria, flavobacteria and actinobacteria[1].
CAS Number
750590-18-2
UNSPSC
12352005
Hazard Statement
H315-H319-H335
Target
Antibiotic; Bacterial
Type
Natural Products
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/tropodithietic-acid.html
Solubility
10 mM in DMSO
Smiles
O=C1C=CC=C2C(SS2)=C1C(O)=O
Molecular Formula
C8H4O3S2
Molecular Weight
212.25
Precautions
P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P362+P364-P403+P233-P405-P501
References & Citations
[1]Rabe P, et al. Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid. Beilstein J Org Chem. 2014 Aug 6;10:1796-801.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Tropodithietic acid

Tropodithietic acid is a monocarboxylic acid that is 8,9-dithiabicyclo[5.2.0]nona-1,3,6-triene substituted by a carboxy group at position 2 and an oxo group at position 3. It is a broad spectrum antibiotic produced by the marine bacterium Phaeobacter inhibens that also acts as a signalling molecule at lower concentrations. It has a role as a toxin, an antibacterial agent, a signalling molecule, a marine metabolite and a bacterial metabolite. It is a monocarboxylic acid, an organic heterobicyclic compound, an organic disulfide, an organosulfur heterocyclic compound and a cyclic ketone. It is a tautomer of a thiotropocin.

CAS Number750590-18-2
PubChem CID44632924
IUPAC Name3-oxo-8,9-dithiabicyclo[5.2.0]nona-1,4,6-triene-2-carboxylic acid
Molecular FormulaC8H4O3S2
Molecular Weight212.2
XLogP1.5
Topological Polar Surface Area105
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Heavy Atom Count13
Formal Charge0
Complexity390
SMILES
C1=CC(=O)C(=C2C(=C1)SS2)C(=O)O
InChI
InChI=1S/C8H4O3S2/c9-4-2-1-3-5-7(13-12-5)6(4)8(10)11/h1-3H,(H,10,11)
InChIKey
BLFCMITWMARUSM-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Tropodithietic acid
CAS: 750590-18-2
CID: 44632924
Formula: C8H4O3S2
MW: 212.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight212.2
XLogP31.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass211.96018633
Monoisotopic Mass211.96018633
Topological Polar Surface Area105 Ų
Heavy Atom Count13
Formal Charge0
Complexity390
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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