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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

Gramicidin
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 Weight 1882.3 g/mol
Molecular Formula C99H140N20O17
XLogP310.7
Hydrogen Bond Donor Count21
Hydrogen Bond Acceptor Count17
Rotatable Bond Count52
Exact Mass1882.07388791 g/mol
Monoisotopic Mass1881.07053308 g/mol
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
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


API Reference Price

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13-Mar-2021
31-May-2024
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