(3E,5Z,7R,8S,9S,11Z,13Z,15S,16R)-16-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-2,4-dihydroxy-5-methyl-6-(propan-2-yl)oxan-2-yl]-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one

• ChemBase ID: 134195
• Molecular Formular: C35H58O9
• Molecular Mass: 622.82962
• Monoisotopic Mass: 622.40808344
• 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)[C@]1(C[C@H]([C@@H]([C@H](O1)C(C)C)C)O)O)O)OC)/C
• Canonical SMILES: CO[C@H]1/C=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]([C@@]1(O)C[C@@H](O)[C@@H]([C@H](O1)C(C)C)C)C)O)C)\OC)/C)C
• InChI: InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12-,20-13-,21-16-,29-17+/t22-,23+,24-,25-,26-,27+,28-,30-,31+,32+,33+,35+/m0/s1
• InChIKey: XDHNQDDQEHDUTM-ROZMNZCYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E,5Z,7R,8S,9S,11Z,13Z,15S,16R)-16-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-2,4-dihydroxy-5-methyl-6-(propan-2-yl)oxan-2-yl]-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
• IUPAC Traditional name: (3E,5Z,7R,8S,9S,11Z,13Z,15S,16R)-16-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-2,4-dihydroxy-6-isopropyl-5-methyloxan-2-yl]-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
• Synonyms: Bafilomycin A1 from Streptomyces griseus

Database IDs

• CAS Number: 88899-55-2
• MDL Number: MFCD06795130
• Beilstein Number: 4730700
• PubChem SID: 24891613; 162228472
• PubChem CID: 24870922

CALCULATED PROPERTIES

• Acid pKa: 11.689453
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 5.0815225
• LogD (pH = 7.4): 5.0815005
• Log P: 5.081523
• Molar Refractivity: 174.5282 cm^3
• Polarizability: 68.10323 Å^3
• Polar Surface Area: 134.91 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - B1793

Biochem/physiol Actions
A specific inhibitor of vacuolar type H+-ATPase (V-ATPase) in animal cells, plant cells and microorganisms.