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. This is in contrast to unrelated gramicidin S, which is a cyclic peptide.

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)
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)^Y Key:IUAYMJGZBVDSGL-UHFFFAOYSA-N^Y
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