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    Gramicidin

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    2D Structure
    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

    2D Structure

    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