gramicidin D

Also known as Gramicidin, Gramicidine, Gramicidin A, Gramicidin B, Gramicidin C, Bacillus brevis gramicidin D

Gramicidin, also called gramicidin D, is a mix of ionophoric antibiotics, gramicidin A, B and C, which make up about 80%, 5%, and 15% of the mix, respectively. Each has 2 isoforms, so the mix has 6 different types of gramicidin molecules. They can be extracted from Brevibacillus brevis soil bacteria. Gramicidins are linear peptides with 15 amino acids. This is in contrast to unrelated gramicidin S, which is a cyclic peptide.

Key facts

Protein family.Symbol: N/A
Protein family.image: Gramicidin A.gif
Protein family.width: 300
Protein family.caption: Gramicidin A head-to-head dimer
Protein family.TCDB: 1.D.1
Protein family.OPM family: 65
Protein family.OPM protein: 1grm

via Wikipedia infobox

Chemical data

Formula: C96H135N19O16
Molecular weight: 1811.2 g/mol
IUPAC name: (2R)-2-[[2-[[(2S)-2-formamido-3-methylbutanoyl]amino]acetyl]amino]-N-[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-(2-hydroxyethylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]-4-methylpentanamide
SMILES: C[C@@H](C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC5=CNC6=CC=CC=C65)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)[C@@H](CC(C)C)NC(=O)CNC(=O)[C@H](C(C)C)NC=O
InChIKey: NDAYQJDHGXTBJL-MWWSRJDJSA-N
XLogP: 10.9
Polar surface area: 520 Å²
H-bond donors: 20
H-bond acceptors: 16
Formal charge: 0

via PubChem

Research

4,349 papers

Gramicidin D conformation, dynamics and membrane ion transport.Biopolymers · 1999
Gramicidin D enhances the antibacterial activity of fluoride.Bioorganic & medicinal chemistry letters · 2014
In Silico and In Vitro Inhibition of SARS-CoV-2 PL(pro) with Gramicidin D.International journal of molecular sciences · 2023
Gramicidin D and dithiothreitol effects on erythrocyte exovesiculation.Cell biochemistry and biophysics · 2005
Gramicidin A in Asymmetric Lipid Membranes.Biomolecules · 2024

via PubMed

Wikidata facts

Subclass of: extract
Mass: 1811.036774
Has use: medication

Show 4 more facts

Commons category: Gramicidin
chemical formula: C₉₆H₁₃₅N₁₉O₁₆
canonical SMILES: CC(C)CC(C(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(C)C)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CC(C)C)C(=O)NC(CC5=CNC6=CC=CC=C65)C(=O)NC(CC(C)C)C(=O)NC(CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)CNC(=O)C(C(C)C)NC=O
isomeric SMILES: C[C@@H](C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC5=CNC6=CC=CC=C65)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)[C@@H](CC(C)C)NC(=O)CNC(=O)[C@H](C(C)C)NC=O

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Encyclopedic overview

5 sections

Contents

Medical uses
History
Structure and chemistry
Pharmacological effect
References

==Medical uses== Gramicidins work as antibiotics against gram-positive bacteria like Bacillus subtilis and Staphylococcus aureus, but not well against gram-negative ones like E. coli.

Excerpted from Wikipedia’s “gramicidin D” article, available under the CC BY-SA 4.0 licence.

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