zinc(2+) ion (4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-5-yl]formamido}-4-methylpentanamido]-4-{[(1S,2S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-3-(carbamoylmethyl)-6-(carboxylatomethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}butanoate

• ChemBase ID: 130851
• Molecular Formular: C66H101N17O16SZn
• Molecular Mass: 1486.05744
• Monoisotopic Mass: 1483.66243324
• 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)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)[O-])NC(=O)[C@H](CC(C)C)NC(=O)C1CN=C(S1)C(C(C)CC)N)CC(=O)N)CC(=O)[O-])Cc1cnc[nH]1)Cc1ccccc1.[Zn+2]
• Canonical SMILES: NCCC[C@H]1NC(=O)[C@H](CCCCNC(=O)[C@H](CC(=O)N)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)[C@H](CC)C)Cc1ccccc1)Cc1[nH]cnc1)CC(=O)[O-])NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)C1CN=C(S1)C(C(CC)C)N)CC(C)C)CCC(=O)[O-].[Zn+2]
• InChI: InChI=1S/C66H103N17O16S.Zn/c1-9-35(6)52(69)66-72-32-48(100-66)63(97)80-43(26-34(4)5)59(93)75-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)76-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-73-39)77-60(94)44(27-38-18-13-12-14-19-38)81-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)74-56(40)90;/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,73)(H,71,89)(H,74,90)(H,75,93)(H,76,98)(H,77,94)(H,78,96)(H,79,95)(H,80,97)(H,81,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88);/q;+2/p-2/t35?,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48?,52?,53-,54-;/m0./s1
• InChIKey: NKULICGUDKGGRL-FCHFGNCGSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: zinc(2+) ion (4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-5-yl]formamido}-4-methylpentanamido]-4-{[(1S,2S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-3-(carbamoylmethyl)-6-(carboxylatomethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}butanoate
• IUPAC Traditional name: zinc(2+) ion (4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-5-yl]formamido}-4-methylpentanamido]-4-{[(1S,2S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-3-(carbamoylmethyl)-6-(carboxylatomethyl)-9-(3H-imidazol-4-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}butanoate
• Synonyms: Bacitracin zinc salt; Zinc bacitracin; 杆菌肽锌; 杆菌肽 锌盐

Database IDs

• CAS Number: 1405-89-6
• EC Number: 215-787-8
• MDL Number: MFCD00130598
• PubChem SID: 162225129; 24892095; 24891810
• PubChem CID: 57402735

CALCULATED PROPERTIES

• Acid pKa: 3.4586437
• H Acceptors: 20
• H Donor: 15
• LogD (pH = 5.5): -7.635476
• LogD (pH = 7.4): -7.1978397
• Log P: -7.2495475
• Molar Refractivity: 385.3236 cm^3
• Polarizability: 142.77258 Å^3
• Polar Surface Area: 536.53 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble50 mg/mL, clear, yellow
• Melting Point: 250 °C (dec.)(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Suitability: meets USP testing specifications
• Biological Source: from Bacillus licheniformis
• Loss on Drying: ≤5% loss on drying
• Empirical Formula (Hill Notation): C66H101N17O16SZn

DETAILS

Sigma Aldrich - B5150

Application
Bacitracin zinc salt is a peptide antibiotic used to study dysruption of bacterial cell wall synthesis at the level of peptidoglycan biosynthesis and isoprenyl metabolism. It is used to study the biosynthesis of sterols and squalene.
Biochem/physiol Actions
Bacitracin is a protease inhibitor. Antimicrobial spectrum: Gram-positive bacteria. Mode of Action: Inhibits bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphate.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - B8800

Application
Bacitracin is used to study the disruption of bacterial cell wall synthesis at the level of peptidoglycan biosynthesis and isoprenyl metabolism. Used to study the biosynthesis of sterols and squalene.