(3S,6S,12R,15S,18S,27S,30S,33S)-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: 179432
• Molecular Formular: C54H90N6O18
• Molecular Mass: 1111.3218
• Monoisotopic Mass: 1110.63116007
• SMILES: [C@@H]1(C(C)C)C(=O)NC(C(=O)O[C@H](C(=O)N[C@H](C(=O)OC(C(C)C)C(=O)N[C@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)OC(C(=O)NC(C(=O)O[C@H](C(=O)N[C@@H](C(C)C)C(=O)O1)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(NC(=O)C(OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)C(OC(=O)[C@@H](NC(=O)[C@@H](OC(=O)C(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-GXCNOZDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,12R,15S,18S,27S,30S,33S)-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: (6R,9S,12S,21S,24S,27S,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: 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; 1Cyclo(D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl); NSC 122023; Valinomicin; Valinomycin

Database IDs

• CAS Number: 2001-95-8
• PubChem SID: 164235342
• PubChem CID: 71752904

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

DETAILS

Toronto Research Chemicals - V094370

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. Used as insecticid

REFERENCES

• Ivanov, et al.: Biochem. Biophys. Res. Commun., 34, 803 (1969)
• Duax, et al.: Science, 176, 911 (1969)