(2S)-2-{[(4R,7S,10S,13S,16S,19S,22S,25S,28R)-28-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-4-methylpentanamido]-13,22-bis[(2S)-butan-2-yl]-10,25-bis(3-carbamimidamidopropyl)-6,9,12,15,18,21,24,27-octaoxo-7,16,19-tris(propan-2-yl)-1,2-dithia-5,8,11,14,17,20,23,26-octaazacyclononacosan-4-yl]formamido}-5-carbamimidamidopentanoic acid

• ChemBase ID: 153777
• Molecular Formular: C63H118N24O13S2
• Molecular Mass: 1483.89402
• Monoisotopic Mass: 1482.87516196
• SMILES: CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](CSSC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)C(C)C)CCCNC(=N)N)[C@@H](C)CC)C(C)C)C(C)C
• Canonical SMILES: CC[C@@H]([C@@H]1NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@H](CSSC[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)C(C)C)C(C)C)[C@H](CC)C)CCCNC(=N)N)C(C)C)C(=O)N[C@H](C(=O)O)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(=N)N)N)CC(C)C)C
• InChI: InChI=1S/C63H118N24O13S2/c1-13-34(11)46-57(97)78-38(21-17-25-75-62(69)70)49(89)83-43(31(5)6)54(94)82-42(53(93)79-39(59(99)100)22-18-26-76-63(71)72)29-102-101-28-41(81-51(91)40(27-30(3)4)80-48(88)36(64)19-15-23-73-60(65)66)52(92)77-37(20-16-24-74-61(67)68)50(90)86-47(35(12)14-2)58(98)85-44(32(7)8)55(95)84-45(33(9)10)56(96)87-46/h30-47H,13-29,64H2,1-12H3,(H,77,92)(H,78,97)(H,79,93)(H,80,88)(H,81,91)(H,82,94)(H,83,89)(H,84,95)(H,85,98)(H,86,90)(H,87,96)(H,99,100)(H4,65,66,73)(H4,67,68,74)(H4,69,70,75)(H4,71,72,76)/t34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-/m0/s1
• InChIKey: RHISNKCGUDDGEG-CJMCYECYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(4R,7S,10S,13S,16S,19S,22S,25S,28R)-28-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-4-methylpentanamido]-13,22-bis[(2S)-butan-2-yl]-10,25-bis(3-carbamimidamidopropyl)-6,9,12,15,18,21,24,27-octaoxo-7,16,19-tris(propan-2-yl)-1,2-dithia-5,8,11,14,17,20,23,26-octaazacyclononacosan-4-yl]formamido}-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: (2S)-2-{[(4R,7S,10S,13S,16S,19S,22S,25S,28R)-28-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-4-methylpentanamido]-13,22-bis[(2S)-butan-2-yl]-10,25-bis(3-carbamimidamidopropyl)-7,16,19-triisopropyl-6,9,12,15,18,21,24,27-octaoxo-1,2-dithia-5,8,11,14,17,20,23,26-octaazacyclononacosan-4-yl]formamido}-5-carbamimidamidopentanoic acid
• Synonyms: Bactenecin

Database IDs

• MDL Number: MFCD00236810
• PubChem SID: 162247916
• PubChem CID: 46735191

CALCULATED PROPERTIES

• Acid pKa: -1.1964736
• H Acceptors: 26
• H Donor: 25
• LogD (pH = 5.5): -14.850135
• LogD (pH = 7.4): -13.155672
• Log P: -5.985318
• Molar Refractivity: 426.2027 cm^3
• Polarizability: 149.90756 Å^3
• Polar Surface Area: 631.02 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C63H118N24O13S2

DETAILS

Sigma Aldrich - B2809

Amino Acid Sequence
Arg-Leu-Cys-Arg-Ile-Val-Val-Ile-Arg-Val-Cys-Arg-OH (Disulfide bridge: 3-11)
Other Notes
Peptide antibiotic, originally isolated from bovine neutrophil granules
Application
Bactenecin is a 12-amino acid cationic antimicrobial peptide from bovine neutrophils. Bactenecin′s activity has been studied as a cyclic molecule as well as in a linear form 1. It is used to study the functional role of Trk1p in the mechanism of other antifungal peptides 2. It has been used to study chemokine and cytokine production, alteration of gene expression in host cells, and inhibition of proinflammatory responses of host cells to bacterial components 3.