(2R,4R,5S,6R)-2-hydroxy-2-[(2S,3R,4S)-3-hydroxy-4-[(2R,3S,9S,10S,11R)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl]-5-methyl-6-(propan-2-yl)oxan-4-yl 3-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]prop-2-enoate

• ChemBase ID: 155899
• Molecular Formular: C44H65NO13
• Molecular Mass: 815.9858
• Monoisotopic Mass: 815.44559115
• SMILES: C[C@H]1C/C(=C\C=C[C@H]([C@H](OC(=O)/C(=C\C(=C\[C@H]([C@H]1O)C)\C)/OC)[C@@H](C)[C@H]([C@H](C)C1(C[C@H]([C@@H]([C@H](O1)C(C)C)C)OC(=O)/C=C/C(=O)NC1=C(CCC1=O)O)O)O)OC)/C
• Canonical SMILES: CO[C@@H]1C=C/C=C(/C)\C[C@H](C)[C@H](O)[C@@H](/C=C(/C=C(\C(=O)O[C@@H]1[C@H]([C@H]([C@@H](C1(O)C[C@@H](OC(=O)/C=C/C(=O)NC2=C(O)CCC2=O)[C@@H]([C@H](O1)C(C)C)C)C)O)C)/OC)\C)C
• InChI: InChI=1S/C44H65NO13/c1-23(2)41-28(7)35(56-37(49)18-17-36(48)45-38-31(46)15-16-32(38)47)22-44(53,58-41)30(9)40(51)29(8)42-33(54-10)14-12-13-24(3)19-26(5)39(50)27(6)20-25(4)21-34(55-11)43(52)57-42/h12-14,17-18,20-21,23,26-30,33,35,39-42,46,50-51,53H,15-16,19,22H2,1-11H3,(H,45,48)/t26-,27+,28-,29-,30-,33-,35+,39-,40+,41+,42+,44+/m0/s1
• InChIKey: KFUFLYSBMNNJTF-CPDCVEHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5S,6R)-2-hydroxy-2-[(2S,3R,4S)-3-hydroxy-4-[(2R,3S,9S,10S,11R)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl]-5-methyl-6-(propan-2-yl)oxan-4-yl 3-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]prop-2-enoate
• IUPAC Traditional name: (2R,4R,5S,6R)-2-hydroxy-2-[(2S,3R,4S)-3-hydroxy-4-[(2R,3S,9S,10S,11R)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl]-6-isopropyl-5-methyloxan-4-yl 3-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]prop-2-enoate
• Synonyms: Bafilomycin B1 from Streptomyces sp.

Database IDs

• CAS Number: 88899-56-3
• Beilstein Number: 4640118
• PubChem SID: 162250037
• PubChem CID: 71312233

CALCULATED PROPERTIES

• Acid pKa: 8.590598
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 5.039109
• LogD (pH = 7.4): 5.0123324
• Log P: 5.0394616
• Molar Refractivity: 222.854 cm^3
• Polarizability: 85.5787 Å^3
• Polar Surface Area: 207.38 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: NG8841000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C44H65NO13

DETAILS

Sigma Aldrich - 11707

Warning
Fatal if swallowed.Bafilomycin B1 is fatal if it is inhaled, swallowed, or if it comes in contact with skin.
Application
Bafilomycin B1 is a toxic macrolide antibiotic used to study cell processes such as autophagy, pH control within cells, and mechanisms of apoptosis 1,2.
Biochem/physiol Actions
Bafilomycin B1 inhibits vacuolar type H+-ATPase (V-ATPase) and is used to study cell processes such as autophagy, pH control within cells, and mechanisms of apoptosis.
Bafilomycin B1 inhibits vacuolar type H+-ATPase (V-ATPase). Bafilomycin B1′s activity results from the presence of a large macrocyclic lactone ring to which deoxy sugars may attach.