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netropsin
Sign in to saveNetropsin (also termed congocidine or sinanomycin) is a polyamide with antibiotic and antiviral activity. Netropsin was discovered by Finlay et al., and first isolated from the actinobacterium Streptomyces netropsis. It belongs to the class of pyrrole-amidine antibiotics.
Chemical data
- Formula
- C18H26N10O3
- Molecular weight
- 430.5 g/mol
- IUPAC name
- N-[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]-4-[[2-(diaminomethylideneamino)acetyl]amino]-1-methylpyrrole-2-carboxamide
- SMILES
- CN1C=C(C=C1C(=O)NC2=CN(C(=C2)C(=O)NCCC(=N)N)C)NC(=O)CN=C(N)N
- InChIKey
- IDBIFFKSXLYUOT-UHFFFAOYSA-N
- XLogP
- -3.1
- Polar surface area
- 211 Ų
- H-bond donors
- 7
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
791 papers- Carbocyclic Analogues of Distamycin and Netropsin.Mini reviews in medicinal chemistry · 2019
- Transcriptional Regulation of Congocidine (Netropsin) Biosynthesis and Resistance.Applied and environmental microbiology · 2021
- Netropsin, a minor groove binding ligand: a potential radioprotective agent.Radiation research · 2009
- Examining the Effects of Netropsin on the Curvature of DNA A-Tracts Using Electrophoresis.Molecules (Basel, Switzerland) · 2021
- Sequence-specific DNA minor groove binders. Design and synthesis of netropsin and distamycin analogues.Bioconjugate chemistry · 1998
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 430.219
Show 3 more facts
- canonical SMILES
- CN1C=C(C=C1C(=O)NC2=CN(C(=C2)C(=O)NCCC(=N)N)C)NC(=O)CN=C(N)N
- chemical formula
- C₁₈H₂₆N₁₀O₃
- isomeric SMILES
- [H]/N=C(/CCNC(=O)C1=CC(=CN1C)NC(=O)C2=CC(=CN2C)NC(=O)CN=C(N)N)\N
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- DNA binding properties
- Antibiotic properties
- See also
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 416422024 | ImageFile =Netropsin.png | ImageClass = skin-invert-image | IUPACName = N-{5-[(3-Amino-3-iminopropyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl}-4-[(N-carbamimidoylglycyl)amino]-1-methyl-1H-pyrrole-2-carboxamide | OtherNames = Nt, congocidin, sinanomycin | Section1 = | Section2 = }} Netropsin (also termed congocidine or sinanomycin) is a polyamide with antibiotic and antiviral activity. Netropsin was discovered by Finlay et al., and first isolated from the actinobacterium Streptomyces netropsis. It belongs to the class of pyrrole-amidine antibiotics.
== DNA binding properties == Netropsin binds to the minor groove of AT-rich sequences of double stranded DNA. In contrast, netropsin does not bind single stranded DNA or double stranded RNA. Crystallographic structures of DNA-bound Netropsin have been obtained and elucidate details of how the drug binds in the minor groove. In the bound structure, the drug makes hydrogen bonding interactions with four subsequent base pairs of the DNA duplex, locally displacing the water molecules of the spine of hydration.
Excerpted from Wikipedia’s “netropsin” article, available under the CC BY-SA 4.0 licence.