sodium (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoate

• ChemBase ID: 134207
• Molecular Formular: C40H67NaO11
• Molecular Mass: 746.94315
• Monoisotopic Mass: 746.45810725
• SMILES: C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)[O-])C[C@@H]1C[C@H]([C@H]([C@@]2(O1)[C@@H](C[C@@](O2)(C)[C@H]1CC[C@@](O1)(C)[C@H]1[C@H](C[C@@H](O1)[C@@H]1[C@H](C[C@H]([C@@](O1)(CO)O)C)C)C)C)C)OC.[Na+]
• Canonical SMILES: CO[C@@H]1C[C@@H](C[C@H]2CC[C@@H]([C@@H](O2)[C@H](C(=O)[O-])C)C)O[C@@]2([C@@H]1C)O[C@](C[C@H]2C)(C)[C@H]1CC[C@@](O1)(C)[C@@H]1O[C@H](C[C@@H]1C)[C@H]1O[C@@](O)(CO)[C@@H](C[C@@H]1C)C.[Na+]
• InChI: InChI=1S/C40H68O11.Na/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34;/h21-35,41,44H,11-20H2,1-10H3,(H,42,43);/q;+1/p-1/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+;/m0./s1
• InChIKey: MOYOTUKECQMGHE-PDEFJWSRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoate
• IUPAC Traditional name: sodium (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoate
• Synonyms: Antibiotic K178; Antibiotic X464; Azalomycin M; Helexin C; Polyetherin A; Nigericin sodium salt

Database IDs

• CAS Number: 28643-80-3
• MDL Number: MFCD00036825
• Beilstein Number: 3892398
• PubChem SID: 24897813; 162228484
• PubChem CID: 16760591

CALCULATED PROPERTIES

• Acid pKa: 4.070921
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): 4.6652822
• LogD (pH = 7.4): 2.9897304
• Log P: 6.106806
• Molar Refractivity: 199.9347 cm^3
• Polarizability: 76.59173 Å^3
• Polar Surface Area: 145.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble10 mg/mL, clear, colorless

Safety Information

• RTECS: QT6840000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC); ≥98.0% (TLC)
• Biological Source: from Streptomyces hygroscopicus
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C40H67NaO11

DETAILS

Sigma Aldrich - N7143

Biochem/physiol Actions
Ionophore which disrupts membrane potential and stimulates ATPase activity in mitochondria.
Polyether ionophore which disrupts membrane potential and stimulates ATPase activity in mitochondria. Ion selectivity is K+> Rb+≥ Cs+>> Na+.
Other Notes
As ion-selective electrode - an efficient K+-carrier.1,2

Sigma Aldrich - 72445

Biochem/physiol Actions
Polyether ionophore which disrupts membrane potential and stimulates ATPase activity in mitochondria. Ion selectivity is K+> Rb+≥ Cs+>> Na+.
Other Notes
As ion-selective electrode - an efficient K+-carrier.1,2
As ion-selective electrode - an efficient K+-carrier1,2