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Gramicidin A

CAT: 0804-HY-P2324Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-P2324Size:5 mg
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Description
Gramicidin A is a peptide component of gramicidin, an antibiotic mixture originally isolated from B. brevis. Gramicidin A is a highly hydrophobic channel-forming ionophore that forms channels in model membranes that are permeable to monovalent cations. Gramicidin A induces degradation of hypoxia inducible factor 1 α (HIF-1α) [1][2].
CAS Number
11029-61-1
UNSPSC
12352209
Hazard Statement
H302
Target
Antibiotic; Bacterial; HIF/HIF Prolyl-Hydroxylase
Type
Peptides
Related Pathways
Anti-infection; Metabolic Enzyme/Protease
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/gramicidin-a.html
Purity
98.10
Solubility
DMSO : 100 mg/mL (ultrasonic;warming)
Smiles
C[C@H](NC(CNC([C@@H](NC=O)C(C)C)=O)=O)C(N[C@@H](C(N[C@H](C(N[C@@H](C(N[C@H](C(N[C@@H](C(N[C@H](C(N[C@@H](C(N[C@H](C(N[C@@H](C(N[C@H](C(N[C@@H](C(N[C@H](C(NCCO)=O)CC1=CNC2=CC=CC=C21)=O)CC(C)C)=O)CC3=CNC4=CC=CC=C43)=O)CC(C)C)=O)CC5=CNC6=CC=CC=C65)=O)CC(C)C)=O)CC7=CNC8=CC=CC=C87)=O)C(C)C)=O)C(C)C)=O)C(C)C)=O)C)=O)CC(C)C)=O
Molecular Formula
C99H140N20O17
Molecular Weight
1882.29
Precautions
H302
References & Citations
[1]Takada Y, et al. Discovery of gramicidin A analogues with altered activities by multidimensional screening of a one-bead-one-compound library. Nat Commun. 2020 Oct 1;11 (1) :4935.|[2]David JM, et al. Gramicidin A induces metabolic dysfunction and energy depletion leading to cell death in renal cell carcinoma cells. Mol Cancer Ther. 2013 Nov;12 (11) :2296-307.|[3]David JM, et al. Gramicidin A blocks tumor growth and angiogenesis through inhibition of hypoxia-inducible factor in renal cell carcinoma. Mol Cancer Ther. 2014 Apr;13 (4) :788-99.
Shipping Conditions
Blue Ice
Storage Conditions
-80°C, 2 years; -20°C, 1 year (Powder, sealed storage, away from moisture)
Scientific Category
Peptides
Clinical Information
No Development Reported

Chemical Information

Gramicidin A

Gramicidin is a heterogeneous mixture of six antibiotic peptides obtained from the soil bacterium Bacillus brevis. Gramicidin is active against most Gram-positive bacteria and against select Gram-negative organisms. It is administered as a topical application.

CAS Number11029-61-1
PubChem CID16132269
IUPAC Name(2R)-2-[[(2S)-2-[[2-[[(2S)-2-formamido-3-methylbutanoyl]amino]acetyl]amino]propanoyl]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
Molecular FormulaC99H140N20O17
Molecular Weight1882.3
XLogP10.7
Topological Polar Surface Area549
Hydrogen Bond Donor Count21
Hydrogen Bond Acceptor Count17
Rotatable Bond Count52
Heavy Atom Count136
Formal Charge0
Complexity3980
SMILES
C[C@@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C)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)CNC(=O)[C@H](C(C)C)NC=O
InChI
InChI=1S/C99H140N20O17/c1-51(2)37-73(109-86(123)59(17)107-81(122)49-105-96(133)82(55(9)10)106-50-121)89(126)108-60(18)87(124)117-84(57(13)14)98(135)119-85(58(15)16)99(136)118-83(56(11)12)97(134)116-80(44-64-48-104-72-34-26-22-30-68(64)72)95(132)112-76(40-54(7)8)92(129)115-79(43-63-47-103-71-33-25-21-29-67(63)71)94(131)111-75(39-53(5)6)91(128)114-78(42-62-46-102-70-32-24-20-28-66(62)70)93(130)110-74(38-52(3)4)90(127)113-77(88(125)100-35-36-120)41-61-45-101-69-31-23-19-27-65(61)69/h19-34,45-48,50-60,73-80,82-85,101-104,120H,35-44,49H2,1-18H3,(H,100,125)(H,105,133)(H,106,121)(H,107,122)(H,108,126)(H,109,123)(H,110,130)(H,111,131)(H,112,132)(H,113,127)(H,114,128)(H,115,129)(H,116,134)(H,117,124)(H,118,136)(H,119,135)/t59-,60-,73+,74+,75+,76+,77-,78-,79-,80-,82-,83+,84+,85-/m0/s1
InChIKey
ZWCXYZRRTRDGQE-LUPIJMBPSA-N
Chemical Structure
2D Structure
2D structure of Gramicidin A
CAS: 11029-61-1
CID: 16132269
Formula: C99H140N20O17
MW: 1882.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1882.3
XLogP310.7
Hydrogen Bond Donor Count21
Hydrogen Bond Acceptor Count17
Rotatable Bond Count52
Exact Mass1882.07388791
Monoisotopic Mass1881.07053308
Topological Polar Surface Area549 Ų
Heavy Atom Count136
Formal Charge0
Complexity3980
Isotope Atom Count0
Defined Atom Stereocenter Count14
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
G038-5GGramicidin
MBS3847560-01Gramicidin A

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