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 Number	11029-61-1
PubChem CID	16132269
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 Formula	C99H140N20O17
Molecular Weight	1882.3
XLogP	10.7
Topological Polar Surface Area	549
Hydrogen Bond Donor Count	21
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	52
Heavy Atom Count	136
Formal Charge	0
Complexity	3980

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

CAS: 11029-61-1

CID: 16132269

Formula: C99H140N20O17

MW: 1882.3

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	1882.3
XLogP3	10.7
Hydrogen Bond Donor Count	21
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	52
Exact Mass	1882.07388791
Monoisotopic Mass	1881.07053308
Topological Polar Surface Area	549 Å²
Heavy Atom Count	136
Formal Charge	0
Complexity	3980
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Catalog	Name
G038-5G	Gramicidin
MBS3847560-01	Gramicidin A

Gramicidin A

Chemical Information

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