(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36S,37S)-33-{[(2R,3S,4S,5S,6R)-4-acetamido-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid

• ChemBase ID: 159133
• Molecular Formular: C49H75NO18
• Molecular Mass: 966.1157
• Monoisotopic Mass: 965.49841457
• SMILES: C\1=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@H]([C@H](C[C@](C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]([C@H]1C)O)C)C)O)O)O)O)O)(O)O2)O)C(=O)O)O[C@H]1[C@H]([C@@H]([C@@H]([C@H](O1)C)O)NC(=O)C)O
• Canonical SMILES: O[C@@H]1CC[C@@H](O)[C@H](O)C[C@H](O)C[C@]2(O)C[C@H](O)[C@@H]([C@@H](O2)C[C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H]([C@H]([C@H]([C@@H](OC(=O)C[C@@H](C1)O)C)C)O)C)O[C@@H]1O[C@H](C)[C@H]([C@H]([C@@H]1O)NC(=O)C)O)C(=O)O
• InChI: InChI=1S/C49H75NO18/c1-28-18-16-14-12-10-8-6-7-9-11-13-15-17-19-36(67-48-46(61)43(50-32(5)51)45(60)31(4)66-48)25-40-42(47(62)63)39(57)27-49(64,68-40)26-35(54)23-38(56)37(55)21-20-33(52)22-34(53)24-41(58)65-30(3)29(2)44(28)59/h6-19,28-31,33-40,42-46,48,52-57,59-61,64H,20-27H2,1-5H3,(H,50,51)(H,62,63)/b7-6+,10-8+,11-9+,14-12+,15-13+,18-16+,19-17+/t28-,29-,30-,31+,33+,34+,35-,36-,37+,38+,39-,40?,42-,43-,44+,45+,46-,48-,49+/m0/s1
• InChIKey: DIGUUNRLVBJXKB-BSVRWWRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36S,37S)-33-{[(2R,3S,4S,5S,6R)-4-acetamido-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
• IUPAC Traditional name: (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36S,37S)-33-{[(2R,3S,4S,5S,6R)-4-acetamido-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
• Synonyms: N-Acetylamphotericin B; N-Acetyl Amphotericin B

Database IDs

• CAS Number: 902457-23-2
• PubChem SID: 162253268
• PubChem CID: 71312819

CALCULATED PROPERTIES

• Acid pKa: 3.8797405
• H Acceptors: 17
• H Donor: 12
• LogD (pH = 5.5): -1.8425062
• LogD (pH = 7.4): -3.4412355
• Log P: -0.21727754
• Molar Refractivity: 254.1143 cm^3
• Polarizability: 98.07015 Å^3
• Polar Surface Area: 322.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: >140°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A168310

An Amphotericin B derivative as medical fungicide.

REFERENCES

• Fujii, G., et al.: Biochemistry, 36, 4959 (1997)
• Sykora, J., et al.: Langmuir, 19, 858 (1997)
• Frattarelli, D., et al.: Drugs, 64, 949 (1997)