(1R,5S,6R,8R,11R,17R)-11-{[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-5-[(2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-3-one

• ChemBase ID: 153153
• Molecular Formular: C40H66O10
• Molecular Mass: 706.94604
• Monoisotopic Mass: 706.46559831
• SMILES: CCC(=O)[C@@H](C)[C@H]([C@H](C)C[C@@H](C)[C@H]1[C@@H](C[C@H](C=C[C@H](CCC/C=C(\[C@@H]2C(=CC[C@@](O2)(CC(=O)O1)O)C)/C)O[C@H]1C[C@H]([C@@H]([C@H](O1)C)O)O)C)C)O
• Canonical SMILES: CCC(=O)[C@H]([C@H]([C@@H](C[C@H]([C@@H]1OC(=O)C[C@@]2(O)CC=C([C@H](O2)/C(=C\CCC[C@@H](C=C[C@@H](C[C@H]1C)C)O[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)O)/C)C)C)C)O)C
• InChI: InChI=1S/C40H66O10/c1-10-32(41)29(8)36(44)26(5)20-28(7)38-27(6)19-23(2)15-16-31(48-35-21-33(42)37(45)30(9)47-35)14-12-11-13-24(3)39-25(4)17-18-40(46,50-39)22-34(43)49-38/h13,15-17,23,26-31,33,35-39,42,44-46H,10-12,14,18-22H2,1-9H3/t23-,26+,27+,28+,29+,30+,31+,33+,35-,36-,37+,38-,39+,40+/m0/s1
• InChIKey: VIOYQVOQUWWSAB-ILYXGRNWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5S,6R,8R,11R,17R)-11-{[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-5-[(2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-3-one
• IUPAC Traditional name: (1R,5S,6R,8R,11R,17R)-11-{[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-5-[(2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-3-one
• Synonyms: Aabomycin A1; Venturicidin A

Database IDs

• CAS Number: 33538-71-5
• EC Number: 251-568-3
• MDL Number: MFCD00036323
• PubChem SID: 24724663; 162247293
• PubChem CID: 71311598

CALCULATED PROPERTIES

• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 6.7239475
• LogD (pH = 7.4): 6.723926
• Log P: 6.723948
• Molar Refractivity: 194.2995 cm^3
• Polarizability: 76.90651 Å^3
• Polar Surface Area: 151.98 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 11.692745

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; ethanol: soluble; methanol: soluble
• Apperance: lyophilized powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Biological Source: from Streptomyces sp.
• Empirical Formula (Hill Notation): C41H67NO11

DETAILS

Sigma Aldrich - V6264

Biochem/physiol Actions
Antifungal antibiotic; uncoupler of mitchondrial oxidative phosphorylation, F0F1-ATPase (ATP synthase) inhibitor.