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Gramicidin

Synopsis, Chemistry

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Also known as: Gramicidin, 1405-97-6, Gramicidinum, Gramicidine, Gramoderm, 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 Formula

C₉₉H₁₄₀N₂₀O₁₇

Molecular Weight

1882.3 g/mol

InChI Key

ZWCXYZRRTRDGQE-SORVKSEFSA-N

A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.

1 2D Structure

Gramicidin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-[[(2S)-2-[[2-[[(2S)-2-formamido-3-methylbutanoyl]amino]acetyl]amino]propanoyl]amino]-N-[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-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

2.1.2 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

2.1.3 InChI Key

ZWCXYZRRTRDGQE-SORVKSEFSA-N

2.1.4 Canonical SMILES

CC(C)CC(C(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(C)C)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CC(C)C)C(=O)NC(CC5=CNC6=CC=CC=C65)C(=O)NC(CC(C)C)C(=O)NC(CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)C(C)NC(=O)CNC(=O)C(C(C)C)NC=O

2.1.5 Isomeric 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

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Gramicidin

2. Gramicidin A

3. Gramicidin A(1)

4. Gramicidin B

5. Gramicidin C

6. Gramicidin D

7. Gramicidin Dubos

8. Gramicidin J

9. Gramicidin K

10. Gramicidin Nf

11. Gramicidin P

12. Gramicidin S

13. Gramicidin, Linear

14. Gramicidins

15. Gramoderm

16. Linear Gramicidin

2.2.2 Depositor-Supplied Synonyms

1. Gramicidin

2. 1405-97-6

3. Gramicidinum

4. Gramicidine

5. Gramoderm

6. 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

7. Gramicidine [inn-french]

8. Gramicidinum [inn-latin]

9. Gramicidina [inn-spanish]

10. Gramicidin [usp:inn:ban]

11. Unii-5ie62321p4

12. Einecs 215-790-4

13. Neosporin Ophthalmic Solution

14. Schembl163104

15. Nsc183503

16. Akos026750031

17. 5ie62321p4

18. Nsc 757043

19. Gramicidin From Bacillus Aneurinolyticus (bacillus Brevis)

20. Hco-val-gly-d-leu-ala-d-val-val-d-val-[trp-d-leu]3-trp-nh2-ch2ch2oh

2.3 Create Date

2007-07-03

3 Chemical and Physical Properties

Molecular Formula	C₉₉H₁₄₀N₂₀O₁₇
Molecular Weight	1882.3 g/mol
XLogP3	10.7
Hydrogen Bond Donor Count	21
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	52
Exact Mass	1882.07388791 g/mol
Monoisotopic Mass	1881.07053308 g/mol
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

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

4.2 ATC Code

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AB - Antibiotics

R02AB30 - Gramicidin