methyl 33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-17-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-1,3,5,7,9,13,37-heptahydroxy-18-methyl-11,15-dioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate

• ChemBase ID: 155177
• Molecular Formular: C59H86N2O19
• Molecular Mass: 1127.31614
• Monoisotopic Mass: 1126.58247854
• SMILES: C[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)OC1CC2C(C(CC(O2)(CC(CC(CC(CC(CC(=O)CC(CC(=O)OC(C(/C=C/C=C\C=C\C=C\C=C\C=C\C=C\1)C)C(C)CCC(CC(=O)c1ccc(cc1)N)O)O)O)O)O)O)O)O)C(=O)OC)O)N)O
• Canonical SMILES: COC(=O)C1C(O)CC2(OC1CC(/C=C/C=C/C=C/C=C/C=C/C=C\C=C\C(C(OC(=O)CC(CC(=O)CC(CC(CC(CC(C2)O)O)O)O)O)C(CCC(CC(=O)c1ccc(cc1)N)O)C)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)O
• InChI: InChI=1S/C59H86N2O19/c1-35-17-15-13-11-9-7-5-6-8-10-12-14-16-18-47(78-58-55(73)53(61)54(72)37(3)77-58)32-50-52(57(74)76-4)49(70)34-59(75,80-50)33-46(68)29-44(66)27-42(64)25-41(63)26-43(65)28-45(67)31-51(71)79-56(35)36(2)19-24-40(62)30-48(69)38-20-22-39(60)23-21-38/h5-18,20-23,35-37,40-42,44-47,49-50,52-56,58,62-64,66-68,70,72-73,75H,19,24-34,60-61H2,1-4H3/t35?,36?,37-,40?,41?,42?,44?,45?,46?,47?,49?,50?,52?,53+,54-,55+,56?,58+,59?/m1/s1
• InChIKey: GIDIUOCSTCGLRW-JMYRJDPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-17-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-1,3,5,7,9,13,37-heptahydroxy-18-methyl-11,15-dioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
• IUPAC Traditional name: methyl 33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-17-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-1,3,5,7,9,13,37-heptahydroxy-18-methyl-11,15-dioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
• Synonyms: Mepartricin

Database IDs

• CAS Number: 11121-32-7
• MDL Number: MFCD00070325
• PubChem SID: 162249315
• PubChem CID: 71312095

CALCULATED PROPERTIES

• Acid pKa: 11.827226
• H Acceptors: 19
• H Donor: 12
• LogD (pH = 5.5): -2.0556488
• LogD (pH = 7.4): -0.8258557
• Log P: 0.8779773
• Molar Refractivity: 303.0931 cm^3
• Polarizability: 116.802086 Å^3
• Polar Surface Area: 368.77 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: RW5692000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - M9149

Application
Mepartricin is a polyene antibacterial with antifungal and antiprotozoal activity. It is an Amphotericin B(AmB) analogue and has been used to study scrapie1. It is used as an antibiotic supplement in cell culture2.
Mepartricin is used in studies on sterol biosynthesis and bacterial cell membranes. It may be incorporated into liposomes