Omiganan Pentahydrochloride

Synopsis, Chemistry

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Also known as: Mbi 226, 269062-93-3, Omiganan hcl, Unii-lx2p9rd54v, Mbi-226, Omiganan pentahydrochloride [usan]

Molecular Formula

C₉₀H₁₃₂Cl₅N₂₇O₁₂

Molecular Weight

1961.4 g/mol

InChI Key

WTNSIKUBZJCPLJ-IQOWARLESA-N

Omiganan Pentahydrochloride is a pentahydrochloride salt of omiganan, a synthetic cationic antimicrobial peptide with wide-spectrum activity against both gram-positive and gram-negative bacteria and fungi. Omiganan pentahydrochloride, an analog of indolicidin, acts by disrupting bacterial cytoplasmic membranes and has been tested in a topical gel for the prevention of catheter-related bloodstream infections.

1 2D Structure

Omiganan Pentahydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-5-carbamimidamido-1-[[(2S)-5-carbamimidamido-1-[[(2S)-1,6-diamino-1-oxohexan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pyrrolidine-2-carboxamide;pentahydrochloride

2.1.2 InChI

InChI=1S/C90H127N27O12.5ClH/c1-5-51(4)75(92)85(127)113-68(41-50(2)3)80(122)109-67(32-18-38-102-90(98)99)79(121)114-71(44-54-48-105-62-27-12-8-23-58(54)62)86(128)116-39-19-34-74(116)84(126)112-70(43-53-47-104-61-26-11-7-22-57(53)61)82(124)115-72(45-55-49-106-63-28-13-9-24-59(55)63)87(129)117-40-20-33-73(117)83(125)111-69(42-52-46-103-60-25-10-6-21-56(52)60)81(123)110-66(31-17-37-101-89(96)97)78(120)108-65(30-16-36-100-88(94)95)77(119)107-64(76(93)118)29-14-15-35-91;;;;;/h6-13,21-28,46-51,64-75,103-106H,5,14-20,29-45,91-92H2,1-4H3,(H2,93,118)(H,107,119)(H,108,120)(H,109,122)(H,110,123)(H,111,125)(H,112,126)(H,113,127)(H,114,121)(H,115,124)(H4,94,95,100)(H4,96,97,101)(H4,98,99,102);5*1H/t51-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-;;;;;/m0...../s1

2.1.3 InChI Key

WTNSIKUBZJCPLJ-IQOWARLESA-N

2.1.4 Canonical SMILES

CCC(C)C(C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)N3CCCC3C(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)NC(CC6=CNC7=CC=CC=C76)C(=O)N8CCCC8C(=O)NC(CC9=CNC1=CC=CC=C19)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)N)N.Cl.Cl.Cl.Cl.Cl

2.1.5 Isomeric SMILES

CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CNC5=CC=CC=C54)C(=O)N[C@@H](CC6=CNC7=CC=CC=C76)C(=O)N8CCC[C@H]8C(=O)N[C@@H](CC9=CNC1=CC=CC=C19)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N)N.Cl.Cl.Cl.Cl.Cl

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Ilrwpwwpwrrk-amide

2. Mbi-226

2.2.2 Depositor-Supplied Synonyms

1. Mbi 226

2. 269062-93-3

3. Omiganan Hcl

4. Unii-lx2p9rd54v

5. Mbi-226

6. Omiganan Pentahydrochloride [usan]

7. Lx2p9rd54v

8. Chembl1793889

9. 626233-83-8

10. L-isoleucyl-l-leucyl-l-arginyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-arginyl-l-arginyl-l-lysinamide Pentahydrochloride

11. L-lysinamide, L-isoleucyl-l-leucyl-l-arginyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-arginyl-l-arginyl-, Hydrochloride (1:5)

12. L-lysinamide, L-isoleucyl-l-leucyl-l-arginyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-arginyl-l-arginyl-, Pentahydrochloride

2.3 Create Date

2007-07-03

3 Chemical and Physical Properties

Molecular Formula	C₉₀H₁₃₂Cl₅N₂₇O₁₂
Molecular Weight	1961.4 g/mol
Hydrogen Bond Donor Count	30
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	52
Exact Mass	1959.896191 g/mol
Monoisotopic Mass	1957.899141 g/mol
Topological Polar Surface Area	647 Å²
Heavy Atom Count	134
Formal Charge	0
Complexity	3790
Isotope Atom Count	0
Defined Atom Stereocenter Count	13
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	6

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)