(4R)-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}-4-[(2S)-4-methyl-2-{[2-(2-methylbutanoyl)-1,3-thiazol-5-yl]formamido}pentanamido]butanoic acid

• ChemBase ID: 161098
• Molecular Formular: C66H98N16O17S
• Molecular Mass: 1419.64632
• Monoisotopic Mass: 1418.70165676
• SMILES: c1c(sc(n1)C(=O)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)c1cnc(s1)C(=O)C(CC)C)CC(C)C)CCC(=O)O
• InChI: InChI=1S/C66H98N16O17S/c1-9-35(6)52(82-58(92)42(22-23-50(84)85)74-59(93)43(26-34(4)5)79-63(97)48-32-71-66(100-48)54(88)37(8)11-3)64(98)75-40-20-15-16-25-70-55(89)46(29-49(68)83)77-62(96)47(30-51(86)87)78-61(95)45(28-39-31-69-33-72-39)76-60(94)44(27-38-18-13-12-14-19-38)80-65(99)53(36(7)10-2)81-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31-37,40-47,52-53H,9-11,15-17,20-30,67H2,1-8H3,(H2,68,83)(H,69,72)(H,70,89)(H,73,90)(H,74,93)(H,75,98)(H,76,94)(H,77,96)(H,78,95)(H,79,97)(H,80,99)(H,81,91)(H,82,92)(H,84,85)(H,86,87)/t35?,36?,37?,40-,41+,42+,43-,44+,45-,46-,47+,52-,53-/m0/s1
• InChIKey: CZWAYUVQAPZALN-APQOTLNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-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}-4-[(2S)-4-methyl-2-{[2-(2-methylbutanoyl)-1,3-thiazol-5-yl]formamido}pentanamido]butanoic acid
• IUPAC Traditional name: (4R)-4-{[(1S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-3-(carbamoylmethyl)-6-(carboxymethyl)-9-(1H-imidazol-4-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-15-(sec-butyl)-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}-4-[(2S)-4-methyl-2-{[2-(2-methylbutanoyl)-1,3-thiazol-5-yl]formamido}pentanamido]butanoic acid
• Synonyms: N-[[2-[(2S)-2-Methyl-1-oxobutyl]-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; Bacitracin F (>80%)

Database IDs

• CAS Number: 22601-63-4
• PubChem SID: 162255233
• PubChem CID: 71313613

CALCULATED PROPERTIES

• H Acceptors: 20
• H Donor: 16
• LogD (pH = 5.5): -5.992034
• LogD (pH = 7.4): -6.84235
• Log P: -5.6777754
• Molar Refractivity: 358.9518 cm^3
• Polarizability: 140.21077 Å^3
• Polar Surface Area: 522.45 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false
• Acid pKa: 3.2351625

DETAILS

Toronto Research Chemicals - B106530

Bacitracin F is a major Bacitracin (B106500) analog, a peptide antibiotic used as an inhibitor of protein disulfide isomerase (PDI).

REFERENCES

• Freedman, R., et al.: Cell, 57, 1069 (1989)
• Noiva, R., et al.: J. Biol. Chem., 267, 3553 (1989)
• Ikai, Y., et al.: J. Antibiot., 48, 233 (1989)
• Lovat, P., et al.: Cancer Res., 68, 5363 (1989)
• Byrne, L., et al.: Biochem. J., 423, 209 (1989)