(3S,6S,9S,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nonakis(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone

• ChemBase ID: 154423
• Molecular Formular: C54H90N6O18
• Molecular Mass: 1111.3218
• Monoisotopic Mass: 1110.63116007
• SMILES: C[C@H]1C(=O)N[C@H](C(=O)O[C@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O1)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C
• Canonical SMILES: C[C@@H]1OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@@H](OC(=O)[C@@H](NC(=O)[C@@H](OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@H](NC1=O)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C
• InChI: InChI=1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34-,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1
• InChIKey: FCFNRCROJUBPLU-RPUZOQEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9S,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nonakis(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone
• IUPAC Traditional name: (3R,6R,9S,12S,15S,18R,21S,24S,27R,30R,33S,36S)-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone
• Synonyms: Valinomycin; Potassium ionophore I; Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)3: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid; Valinomycin; 缬氨霉素; 钾离子载体 I

Database IDs

• CAS Number: 2001-95-8
• EC Number: 217-896-6
• MDL Number: MFCD00005114
• Beilstein Number: 78657
• PubChem SID: 24900743; 162248562; 24881872
• PubChem CID: 16217526

CALCULATED PROPERTIES

• Acid pKa: 11.189129
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): 5.924192
• LogD (pH = 7.4): 5.92413
• Log P: 5.9241924
• Molar Refractivity: 276.8304 cm^3
• Polarizability: 111.62216 Å^3
• Polar Surface Area: 332.4 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 184-190 °C
• Flash Point: 188.6 °F; 87 °C

Safety Information

• RTECS: YV9468000
• European Hazard Symbols: Highly toxic (T+); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 1; 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 21/22; 27/28
• Safety Statements: 28-36/37-45; 36/37
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300 + H310
• GHS Precautionary statements: P264-P280-P301 + P310-P302 + P350-P310
• 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; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC)
• Concentration: ~1 mg/mL in DMSO
• Grade: Selectophore™
• Biological Source: from Streptomyces sp.
• Sterility: 0.2 μm filtered
• Shipped in: wet ice
• Quality: function tested
• Empirical Formula (Hill Notation): C54H90N6O18

DETAILS

Sigma Aldrich - V3639

Application
Valinomycin is a cyclic dodecadepsipeptides with potassium ionophoric properties. It is used to study ion transport in biological systems. It is used to study its inhibitory effect on intact cells and the growth of bacteria and yeast. It is used to induce apoptosis1.
Biochem/physiol Actions
K+-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction.
Valinomycin is a K+-selective ionophoric cyclodepsipeptide. It is a potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction. It is reported to be insecticidal, nematicidal and antiviral1.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 60403

General description
Visit our Sensor Applications portal to learn more.
Other Notes
Important research tool for membrane studies1; As ionophor in membrane electrodes for the determination of K+-activities2,3
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH