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Gramicidin S

CAT: 0804-HY-P5712-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-P5712-01Size:1 mg
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Description
Gramicidin S (Gramicidin soviet) is a cationic cyclic peptide antibiotic that selectively targets bacterial cell membranes and has anticancer activity. Gramicidin S also exerts antibacterial activity by destroying membrane integrity and interfering with membrane protein function. Gramicidin S inserts into the phospholipid bilayer through hydrophobic amino acid residues, specifically binds to negatively charged membrane lipids and disrupts membrane structure, thereby inhibiting cell division and cell wall synthesis, and ultimately causing bacterial death. Gramicidin S also inhibits ion channels, with IC50s of 41 μM, 24 μM, and 3 μM for Na+/K+-ATPase, tobacco leaf plasma membrane Mg2+/K+-ATPase, and rat heart plasma membrane Ca2+-ATPase, respectively[1][2][3].
CAS Number
113-73-5
Product Name Alternative
Gramicidin soviet
UNSPSC
12352209
Target
Antibiotic; Bacterial; Na+/K+ ATPase
Type
Peptides
Related Pathways
Anti-infection; Membrane Transporter/Ion Channel
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/gramicidin-s.html
Purity
99.89
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C1N2[C@](CCC2)([H])C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](C(N3[C@](CCC3)([H])C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H]1CC4=CC=CC=C4)=O)CC(C)C)=O)CCCN)=O)C(C)C)=O)=O)CC5=CC=CC=C5)=O)CC(C)C)=O)CCCN)=O)C(C)C)=O
Molecular Formula
C60H92N12O10
Molecular Weight
1141.45
References & Citations
[1]Mogi T, et al. Gramicidin S and polymyxins: the revival of cationic cyclic peptide antibiotics. Cell Mol Life Sci. 2009 Dec;66 (23) :3821-6.|[2]Wenzel M, et al. The Multifaceted Antibacterial Mechanisms of the Pioneering Peptide Antibiotics Tyrocidine and Gramicidin S. mBio. 2018 Oct 9;9 (5) :e00802-18.|[3]Okamoto K, et al. Inhibitory effect of gramicidin S on the growth of murine tumor cells in vitro and in vivo. Oncology. 1984;41 (1) :43-8.
Shipping Conditions
Blue Ice
Storage Conditions
-80°C, 2 years; -20°C, 1 year (Powder, sealed storage, away from moisture and light)
Scientific Category
Peptides
Clinical Information
No Development Reported

Chemical Information

Gramicidin S

Gramicidin S is a homodetic cyclic peptide.

CAS Number113-73-5
PubChem CID73357
IUPAC Name(3R,6S,9S,12S,15S,21R,24S,27S,30S,33S)-9,27-bis(3-aminopropyl)-3,21-dibenzyl-6,24-bis(2-methylpropyl)-12,30-di(propan-2-yl)-1,4,7,10,13,19,22,25,28,31-decazatricyclo[31.3.0.015,19]hexatriacontane-2,5,8,11,14,20,23,26,29,32-decone
Molecular FormulaC60H92N12O10
Molecular Weight1141.4
XLogP4.6
Topological Polar Surface Area325
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count12
Rotatable Bond Count16
Heavy Atom Count82
Formal Charge0
Complexity2020
SMILES
CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN)C(C)C)CC4=CC=CC=C4)CC(C)C)CCCN)C(C)C)CC5=CC=CC=C5
InChI
InChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m0/s1
InChIKey
IUAYMJGZBVDSGL-XNNAEKOYSA-N
Chemical Structure
2D Structure
2D structure of Gramicidin S
CAS: 113-73-5
CID: 73357
Formula: C60H92N12O10
MW: 1141.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1141.4
XLogP34.6
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count12
Rotatable Bond Count16
Exact Mass1140.70593718
Monoisotopic Mass1140.70593718
Topological Polar Surface Area325 Ų
Heavy Atom Count82
Formal Charge0
Complexity2020
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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