(4R)-4-[(2S)-2-({2-[(1S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-5-yl}formamido)-4-methylpentanamido]-4-{[(1S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-(butan-2-yl)-3-(carbamoylmethyl)-6-(carboxymethyl)-9-(1H-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

• ChemBase ID: 161097
• Molecular Formular: C66H103N17O16S
• Molecular Mass: 1422.69332
• Monoisotopic Mass: 1421.7489413
• SMILES: C1C(SC(=N1)[C@@H](N)C(CC)C)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[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](C(=O)NCCCC1)CC(=O)N)CC(=O)O)Cc1nc[nH]c1)Cc1ccccc1)C(CC)C)CCCN)C(CC)C)CCC(=O)O)CC(C)C
• 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(CC)C)Cc1ccccc1)Cc1nc[nH]c1)CC(=O)O)NC(=O)[C@H](C(CC)C)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)C1CN=C(S1)[C@H](C(CC)C)N)CC(C)C)CCC(=O)O
• InChI: InChI=1S/C66H103N17O16S/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)/t35?,36?,37?,40-,41+,42+,43-,44+,45-,46-,47+,48?,52-,53-,54-/m0/s1
• InChIKey: MNJKVJAYSVAQLU-YOJCIBLDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(2S)-2-({2-[(1S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-5-yl}formamido)-4-methylpentanamido]-4-{[(1S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-(butan-2-yl)-3-(carbamoylmethyl)-6-(carboxymethyl)-9-(1H-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
• IUPAC Traditional name: bacitracin A
• Synonyms: N-[[(4R)-2-[(1S,2S)-1-Amino-2-methylbutyl]-4,5-dihydro-4-thiazolyl]carbonyl]-L-leucyl-D-α-glutamyl-L-isoleucyl-L-lysyl-D-ornithyl-L-isoleucyl-D-phenylalanyl-L-histidyl-D-α-aspartyl-L-asparagine (10→4)-Lactam Deuterated; Zutracin-deuterated; Bacitracin Deuterated; Altracin-deuterated; Ayfivin-deuterated; Baciguent-deuterated; Bacillichin-deuterated; Bacilliquin-deuterated; Fortracin-deuterated; Parentracin-deuterated; Penitracin-deuterated; Topitracin-deuterated; Tropitracin-deuterated; N-[[(4R)-2-[(1S,2S)-1-Amino-2-methylbutyl]-4,5-dihydro-4-thiazolyl]carbonyl]-L-leucyl-D-α-glutamyl-L-isoleucyl-L-lysyl-D-ornithyl-L-isoleucyl-D-phenylalanyl-L-histidyl-D-α-aspartyl-L-asparagine (10→4)-Lactam; Altracin; Ayfivin; Baciguent; Bacillichin; Bacilliquin; Fortracin; Parentracin; Penitracin; Topitracin; Tropitracin; Zutracin; Bacitracin (>80%)

Database IDs

• CAS Number: 1405-87-4
• PubChem SID: 162255232
• PubChem CID: 439542

CALCULATED PROPERTIES

• Acid pKa: 3.4471412
• H Acceptors: 20
• H Donor: 17
• LogD (pH = 5.5): -7.5519357
• LogD (pH = 7.4): -6.8471966
• Log P: -6.889497
• Molar Refractivity: 363.0837 cm^3
• Polarizability: 143.00026 Å^3
• Polar Surface Area: 530.87 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B106500

Bacitracin is a peptide antibiotic effective against gram-postive bacteria. Bacitracin is an inhibitor of peptidoglycan synthesis. Bacitracin disrupts bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphate. Bacitracin also st

Toronto Research Chemicals - B106502

Deuterated analogue of Bacitracin, a peptide antibiotic effective against gram-postive bacteria. Bacitracin is an inhibitor of peptidoglycan synthesis. Bacitracin disrupts bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphat

REFERENCES

• Ward, J.B. et al.: Biochem. J., 141, 227 (1974)
• Anastasi, A. et al.: Biochem. J., 290, 601 (1974)
• Daly, D.J. et al.: Biochem. Soc. Trans., 13, 1161 (1974)
• Weinberg, E.D. et al.: Antibiot. Ber., 90, (1974)
• Ward, J.B. et al.: Biochem. J., 141, 227 (1974)
• Anastasi, A. et al.: Biochem. J., 290, 601 (1974)
• Daly, D.J. et al.: Biochem. Soc. Trans., 13, 1161 (1974)
• Weinberg, E.D. et al.: Antibiot. Ber., 90, (1974)