Valinomycin

Valinomycin
Names
	IUPAC name cyclo[N-oxa-D-alanyl-D-valyl-N-oxa-L-valyl-D-valyl-N-oxa-D-alanyl-D-valyl-N-oxa-L-valyl-L-valyl-N-oxa-L-alanyl-L-valyl-N-oxa-L-valyl-L-valyl]
Identifiers
CAS Number	2001-95-8 ;
3D model (JSmol)	: Interactive image;
ChEBI	CHEBI:28545 ;
ChEMBL	ChEMBL223643 ;
ChemSpider	21493802 ;
DrugBank	DB14057;
ECHA InfoCard	100.016.270
EC Number	217-896-6;
PubChem CID	3000706;
UNII	N561YS75MN ;
UN number	2811 2588
CompTox Dashboard (EPA)	DTXSID9041150 ;
	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 Key: FCFNRCROJUBPLU-DNDCDFAISA-N ; 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+/m1/s1 Key: FCFNRCROJUBPLU-DNDCDFAIBE;
	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;
Properties
Chemical formula	C54H90N6O18
Molar mass	1111.32 g/mol
Appearance	White solid
Melting point	190 °C (374 °F; 463 K)
Solubility	Methanol, ethanol, ethyl acetate, petrol-ether, dichloromethane
UV-vis (λmax)	220 nm
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Neurotoxicant
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310
Precautionary statements	P262, P264, P270, P280, P301+P310, P302+P350, P310, P321, P322, P330, P361, P363, P405, P501
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	4 mg/kg (oral, rat)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Valinomycin is a naturally occurring dodecadepsipeptide used in the transport of potassium and as an antibiotic. Valinomycin is obtained from the cells of several Streptomyces species, S. fulvissimus being a notable one.

It is a member of the group of natural neutral ionophores because it does not have a residual charge. It consists of enantiomers D- and L-valine (Val), D-alpha-hydroxyisovaleric acid, and L-lactic acid. Structures are alternately bound via amide and ester bridges. Valinomycin is highly selective for potassium ions over sodium ions within the cell membrane.^[2] It functions as a potassium-specific transporter and facilitates the movement of potassium ions through lipid membranes "down" the electrochemical potential gradient.^[3] The stability constant K for the potassium-valinomycin complex is nearly 100,000 times larger than that of the sodium-valinomycin complex.^[4] This difference is important for maintaining the selectivity of valinomycin for the transport of potassium ions (and not sodium ions) in biological systems.

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.^[5]

^ ^a ^b "ChemIDplus - 2001-95-8 - FCFNRCROJUBPLU-DNDCDFAISA-N - Valinomycin - Similar structures search, synonyms, formulas, resource links, and other chemical information". TOXNET. U.S. National Library of Medicine. Archived from the original on 20 December 2015.
^ Lars, Rose, Jenkins ATA (2007). "The effect of the ionophore valinomycin on biomimetic solid supported lipid DPPTE/EPC membranes". Bioelectrochemistry. 70 (2): 387–393. doi:10.1016/j.bioelechem.2006.05.009. PMID 16875886.
^ Cammann K (1985). "Ion-selective bulk membranes as models". Top. Curr. Chem. Topics in Current Chemistry. 128: 219–258. doi:10.1007/3-540-15136-2_8. ISBN 978-3-540-15136-4.
^ Rose MC, Henkens RW (1974). "Stability of sodium and potassium complexes of valinomycin". Biochimica et Biophysica Acta (BBA) - General Subjects. 372 (2): 426–435. doi:10.1016/0304-4165(74)90204-9.
^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived (PDF) from the original on February 25, 2012. Retrieved October 29, 2011.

[chemidplus-1] "ChemIDplus - 2001-95-8 - FCFNRCROJUBPLU-DNDCDFAISA-N - Valinomycin - Similar structures search, synonyms, formulas, resource links, and other chemical information". TOXNET. U.S. National Library of Medicine. Archived from the original on 20 December 2015.

[2] Lars, Rose, Jenkins ATA (2007). "The effect of the ionophore valinomycin on biomimetic solid supported lipid DPPTE/EPC membranes". Bioelectrochemistry. 70 (2): 387–393. doi:10.1016/j.bioelechem.2006.05.009. PMID 16875886.

[3] Cammann K (1985). "Ion-selective bulk membranes as models". Top. Curr. Chem. Topics in Current Chemistry. 128: 219–258. doi:10.1007/3-540-15136-2_8. ISBN 978-3-540-15136-4.

[4] Rose MC, Henkens RW (1974). "Stability of sodium and potassium complexes of valinomycin". Biochimica et Biophysica Acta (BBA) - General Subjects. 372 (2): 426–435. doi:10.1016/0304-4165(74)90204-9.

[gov-right-know-5] "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived (PDF) from the original on February 25, 2012. Retrieved October 29, 2011.

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