(1'R,2R,4'S,5S,6R,8'R,10'Z,12'S,13'S,14'Z,20'R,21'R,24'S)-6-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.14,8.020,24]pentacosane]-10',14',16',22'-tetraen-2'-one

• ChemBase ID: 133142
• Molecular Formular: C48H74O14
• Molecular Mass: 875.09276
• Monoisotopic Mass: 874.50785705
• SMILES: CC[C@H](C)[C@@H]1[C@H](CC[C@@]2(O1)C[C@@H]1C[C@H](O2)C/C=C(\[C@H]([C@H](/C=C\C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O1)O)C)O[C@H]1C[C@@H]([C@H]([C@@H](O1)C)O[C@H]1C[C@@H]([C@H]([C@@H](O1)C)O)OC)OC)/C)C
• Canonical SMILES: CO[C@H]1C[C@H](O[C@H]2[C@@H](C)/C=C\C=C/3\CO[C@H]4[C@]3(O)[C@@H](C=C([C@H]4O)C)C(=O)O[C@H]3C[C@@H](C/C=C\2/C)O[C@]2(C3)CC[C@@H]([C@H](O2)[C@H](CC)C)C)O[C@H]([C@@H]1O[C@H]1C[C@H](OC)[C@H]([C@@H](O1)C)O)C
• InChI: InChI=1S/C48H74O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3/b13-12-,27-15-,32-14-/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1
• InChIKey: AZSNMRSAGSSBNP-XKKMCYFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,2R,4'S,5S,6R,8'R,10'Z,12'S,13'S,14'Z,20'R,21'R,24'S)-6-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^4,^8.0^2^0,^2^4]pentacosane]-10',14',16',22'-tetraen-2'-one
• IUPAC Traditional name: (1'R,2R,4'S,5S,6R,8'R,10'Z,12'S,13'S,14'Z,20'R,21'R,24'S)-6-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^4,^8.0^2^0,^2^4]pentacosane]-10',14',16',22'-tetraen-2'-one
• Synonyms: MK-933; Ivermectin; 22,23-Dihydroavermectin B1

Database IDs

• CAS Number: 70288-86-7
• MDL Number: MFCD00869511
• PubChem SID: 162227419; 24278497
• PubChem CID: 71308642

CALCULATED PROPERTIES

• Acid pKa: 12.467905
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 5.8257456
• LogD (pH = 7.4): 5.825742
• Log P: 5.8257456
• Molar Refractivity: 230.3276 cm^3
• Polarizability: 92.01296 Å^3
• Polar Surface Area: 170.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: MEK: soluble50 mg/mL

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 61-28
• Safety Statements: 53-28-36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H360
• GHS Precautionary statements: P201-P264-P301 + P310-P308 + P313
• 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 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ABCB1(5243), CYP3A4(1576)mouse ... Abcb1a(18671), Abcb1b(18669)

DETAILS

Sigma Aldrich - I8898

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Other Notes
Primarily ivermectin B1a.
Biochem/physiol Actions
Positive allosteric modulator of α7 neuronal nicotinic acetylcholine receptor; also modulates glutamate-GABA-activated chloride channels.