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Tyrothricin

Tyrothricin

Synopsis, Chemistry

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Also known as: Bactratycin, Dermotricine, Hydrotricine, Coltirot, Martricin, Ginotricina

Molecular Formula

C₆₅H₈₅N₁₁O₁₃

Molecular Weight

1228.4 g/mol

InChI Key

NLJVXZFCYKWXLH-DXTIXLATSA-N

A polypeptide antibiotic mixture obtained from Bacillus brevis. It consists of a mixture of three tyrocidines (60%) and several gramicidins (20%) and is very toxic to blood, liver, kidneys, meninges, and the olfactory apparatus. It is used topically.

1 2D Structure

Tyrothricin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[(3R,6S,9S,12S,15S,17S,20S,22R,25S,28S)-20-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3,22,25-tribenzyl-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,18,21,24,27-nonaoxo-12-propan-2-yl-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan-17-yl]propanoic acid

2.1.2 InChI

InChI=1S/C65H85N11O13/c1-38(2)32-49-60(84)74-52(36-42-20-12-7-13-21-42)65(89)76-31-15-23-53(76)63(87)73-51(34-41-18-10-6-11-19-41)61(85)70-47(33-40-16-8-5-9-17-40)57(81)48(37-54(67)78)71-59(83)46(28-29-55(79)80)68-50(35-43-24-26-44(77)27-25-43)62(86)75-56(39(3)4)64(88)69-45(22-14-30-66)58(82)72-49/h5-13,16-21,24-27,38-39,45-53,56,68,77H,14-15,22-23,28-37,66H2,1-4H3,(H2,67,78)(H,69,88)(H,70,85)(H,71,83)(H,72,82)(H,73,87)(H,74,84)(H,75,86)(H,79,80)/t45-,46-,47+,48-,49-,50-,51-,52+,53-,56-/m0/s1

2.1.3 InChI Key

NLJVXZFCYKWXLH-DXTIXLATSA-N

2.1.4 Canonical SMILES

CC(C)CC1C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)C(NC(=O)C(NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCN)C(C)C)CC3=CC=C(C=C3)O)CCC(=O)O)CC(=O)N)CC4=CC=CC=C4)CC5=CC=CC=C5)CC6=CC=CC=C6

2.1.5 Isomeric SMILES

CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](C(=O)[C@@H](NC(=O)[C@@H](N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN)C(C)C)CC3=CC=C(C=C3)O)CCC(=O)O)CC(=O)N)CC4=CC=CC=C4)CC5=CC=CC=C5)CC6=CC=CC=C6

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Codtricine

2. Dermotricine

3. Hydrotricine

4. Martricin

5. Tyroderm

6. Tyrosur

2.2.2 Depositor-Supplied Synonyms

1. Bactratycin

2. Dermotricine

3. Hydrotricine

4. Coltirot

5. Martricin

6. Ginotricina

7. Pharothricetten

8. Rinotricina

9. Solutricine

10. Tirotricina

11. Tyrothricine

12. Tyrothricinum

13. Biothricin

14. Triciderm

15. Tyroderm

16. Tyrosur

17. Tyrozets

18. Tyrex

19. Dubos Crude Crystals

20. Intraderm Tyrothricin

21. Caswell No. 900a

22. Tyri 10

23. Tirotricina [inn-spanish]

24. Tyrothricine [inn-french]

25. Tyrothricinum [inn-latin]

26. Einecs 215-771-0

27. Epa Pesticide Chemical Code 006311

28. Gramicidin A & Tyrocidine A

29. Tyrothricin [usp:inn:ban]

30. Unii-877376v2xw

31. Chembl577736

32. Schembl23370285

33. 877376v2xw

34. Nsc 757363

35. An Antibacterial Substance Produced By The Growth Of Bacillus Brevis Dubos (fam. Bacteriaceae)

36. 3-[(3r,6s,9s,12s,15s,17s,20s,22r,25s,28s)-20-(2-amino-2-oxo-ethyl)-9-(3-aminopropyl)-3,22,25-tribenzyl-15-[(4-hydroxyphenyl)methyl]-6-isobutyl-12-isopropyl-2,5,8,11,14,18,21,24,27-nonaoxo-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan-17-yl]propanoic Acid

37. Cyclic (-val-orn-leu-d-phe-pro-phe-d-phe-asn-glu-tyr-) Tyrocidine A & (hco-val-gly-ala-d-leu-ala-d-val-val-d-val-trp-d-leu-trp-d-leu-trp-d-leu-trp-nhch2ch2oh, Ile-gly-ala-d-leu-ala-d-val-val-d-val-trp-d-leu-trp-d-leu-trp-d-leu-trp-nhch2ch2oh) Gramicidin A

2.3 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₆₅H₈₅N₁₁O₁₃
Molecular Weight	1228.4 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	19
Exact Mass	1227.63283181 g/mol
Monoisotopic Mass	1227.63283181 g/mol
Topological Polar Surface Area	380 Å²
Heavy Atom Count	89
Formal Charge	0
Complexity	2390
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
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-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.)

Anti-Bacterial Agents

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