Gramicidin

Gramicidin
	Structure of gramicidin A, B, and C (click to enlarge)
Clinical data
ATC code	R02AB30 (WHO) ;
Identifiers
CAS Number	1405-97-6 ;
PubChem CID	16130140;
DrugBank	DB00027 ;
ChemSpider	3076403 ;
UNII	5IE62321P4;
KEGG	D04369 ;
ChEMBL	ChEMBL557217 ;
ECHA InfoCard	100.014.355
Chemical and physical data
Formula	C99H140N20O17
Molar mass	1882.332 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	229 to 230 °C (444 to 446 °F)
Solubility in water	6 mg/L
	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/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) ; Key:IUAYMJGZBVDSGL-UHFFFAOYSA-N ;
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	Gramicidin A head-to-head dimer
Identifiers
Symbol	N/A
TCDB	1.D.1
OPM superfamily	65
OPM protein	1grm

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.^[2] This is in contrast to unrelated gramicidin S, which is a cyclic peptide.

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[2]

Clinical data
Structure of gramicidin A, B, and C (click to enlarge)
ATC code	R02AB30 (WHO)
Identifiers
CAS Number	1405-97-6^Y
PubChem CID	16130140
DrugBank	DB00027^N
ChemSpider	3076403^Y
UNII	5IE62321P4
KEGG	D04369^Y
ChEMBL	ChEMBL557217^N
ECHA InfoCard	100.014.355
Chemical and physical data
Formula	C₉₉H₁₄₀N₂₀O₁₇
Molar mass	1882.332 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	229 to 230 °C (444 to 446 °F) ^[1]
Solubility in water	6 mg/L^[1]
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/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)^Y Key:IUAYMJGZBVDSGL-UHFFFAOYSA-N^Y
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