(4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-4-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-(carboxymethyl)-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}butanoic acid

• ChemBase ID: 133764
• Molecular Formular: C66H103N17O16S
• Molecular Mass: 1422.69332
• Monoisotopic Mass: 1421.7489413
• 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)C1CSC(=N1)C(C(C)CC)N)CC(=O)N)CC(=O)O)Cc1cnc[nH]1)Cc1ccccc1
• 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)C1CSC(=N1)C(C(CC)C)N)CC(C)C)CCC(=O)O
• InChI: InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(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,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35?,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48?,52?,53-,54-/m0/s1
• InChIKey: CLKOFPXJLQSYAH-RNHDWVCBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-4-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-(carboxymethyl)-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}butanoic acid
• IUPAC Traditional name: (4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-4-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-(carboxymethyl)-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}butanoic acid
• Synonyms: Bacitracin

Database IDs

• CAS Number: 1405-87-4
• EC Number: 215-786-2
• MDL Number: MFCD00062640
• PubChem SID: 24847312; 24891503; 162228041
• PubChem CID: 6714010

CALCULATED PROPERTIES

• Acid pKa: 3.2100034
• H Acceptors: 20
• H Donor: 17
• LogD (pH = 5.5): -7.5808387
• LogD (pH = 7.4): -7.145578
• Log P: -7.196043
• Molar Refractivity: 363.705 cm^3
• Polarizability: 142.99803 Å^3
• Polar Surface Area: 530.87 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Do you have solubility information on this product that you would like to share?; H2O: soluble50 mg/mL, clear to very slightly hazy, deep yellow

Safety Information

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

Product Information

• Impurities: ≤5% water
• Biological Source: from Bacillus licheniformis
• Empirical Formula (Hill Notation): C66H103N17O16S

DETAILS

Sigma Aldrich - 11702

Application
Used to study dysruption of bacterial cell wall synthesis at the level of peptidoglycan biosynthesis and isoprenyl metabolism. Also used to study the biosynthesis of sterols and squalene.
Biochem/physiol Actions
Peptide antibiotic.Antimicrobial spectrum: Gram-positive bacteria.Mode of Action: Inhibits bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphate.

Sigma Aldrich - B0125

Application
Do you have application information on this product that you would like to share?
Used to study dysruption of bacterial cell wall synthesis at the level of peptidoglycan biosynthesis and isoprenyl metabolism.
Biochem/physiol Actions
Peptide antibiotic.Antimicrobial spectrum: Gram-positive bacteria.Mode of Action: Inhibits bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphate.
Antimicrobial spectrum: Gram-positive bacteria. Bacitracin inhibits bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphate.