Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C92H150N22O25 |
| Molecular Weight | 1964.3078 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C[C@@H](NC(=O)CNC(=O)C(C)(C)NC(=O)[C@@H](NC(=O)C(C)(C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]1CCCN1C(=O)C(C)(C)NC(C)=O)C(C)C)C(=O)NC(C)(C)C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@](C)(CCC(N)=O)C(=O)N[C@H](CO)CC3=CC=CC=C3
InChI
InChIKey=NRRXBXXRKXUIFD-ZTEFGAJGSA-N
InChI=1S/C92H150N22O25/c1-47(2)43-58(72(127)108-91(23,24)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-88(17,18)80(135)97-51(8)68(123)102-57(36-38-64(120)121)71(126)112-92(25,40-39-62(94)118)82(137)99-55(46-115)44-54-31-27-26-28-32-54)100-63(119)45-95-77(132)85(11,12)110-76(131)66(49(5)6)104-81(136)89(19,20)107-70(125)56(35-37-61(93)117)101-67(122)50(7)96-78(133)86(13,14)106-69(124)52(9)98-79(134)87(15,16)109-74(129)60-34-30-42-114(60)83(138)90(21,22)105-53(10)116/h26-28,31-32,47-52,55-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,135)(H,98,134)(H,99,137)(H,100,119)(H,101,122)(H,102,123)(H,103,128)(H,104,136)(H,105,116)(H,106,124)(H,107,125)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,126)(H,120,121)/t50-,51-,52-,55-,56-,57-,58+,59-,60-,65-,66-,92-/m0/s1
| Molecular Formula | C92H150N22O25 |
| Molecular Weight | 1964.3078 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 11 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Mechanosensing and signal transduction in tendrils. | 2003 |
|
| Interactions of the M2delta segment of the acetylcholine receptor with lipid bilayers: a continuum-solvent model study. | 2003 Dec |
|
| An Arabidopsis thaliana gene for methylsalicylate biosynthesis, identified by a biochemical genomics approach, has a role in defense. | 2003 Dec |
|
| Metabolic assessment in liver microsomes by co-activating cytochrome P450s and UDP-glycosyltransferases. | 2003 Jul-Sep |
|
| The antibacterial peptide ceratotoxin A displays alamethicin-like behavior in lipid bilayers. | 2003 Nov |
|
| Sequences of alamethicins F30 and F50 reconsidered and reconciled. | 2003 Nov-Dec |
|
| Template-free self-assembling fullerene and lipopeptide conjugates of alamethicin form voltage-dependent ion channels of remarkable stability and activity. | 2003 Nov-Dec |
|
| Channel properties of template assembled alamethicin tetramers. | 2003 Nov-Dec |
|
| Microfabricated teflon membranes for low-noise recordings of ion channels in planar lipid bilayers. | 2003 Oct |
|
| Total synthesis in solution of alamethicin F50/5 by an easily tunable segment condensation approach. | 2004 |
|
| Quantitative evaluation of the effects of mitochondrial permeability transition pore modifiers on accumulation of calcium phosphate: comparison of rat liver and brain mitochondria. | 2004 Apr 1 |
|
| Opening of the mitochondrial permeability transition pore induces reactive oxygen species production at the level of the respiratory chain complex I. | 2004 Apr 23 |
|
| Herbivore-induced defense response in a model legume. Two-spotted spider mites induce emission of (E)-beta-ocimene and transcript accumulation of (E)-beta-ocimene synthase in Lotus japonicus. | 2004 Aug |
|
| Ca2+-induced reactive oxygen species production promotes cytochrome c release from rat liver mitochondria via mitochondrial permeability transition (MPT)-dependent and MPT-independent mechanisms: role of cardiolipin. | 2004 Dec 17 |
|
| Microscopic visualization of alamethicin incorporation into model membrane monolayers. | 2004 Dec 7 |
|
| Impedance analysis and single-channel recordings on nano-black lipid membranes based on porous alumina. | 2004 Feb |
|
| Implicit solvent model estimates of the stability of model structures of the alamethicin channel. | 2004 Feb |
|
| Conformational changes in alamethicin associated with substitution of its alpha-methylalanines with leucines: a FTIR spectroscopic analysis and correlation with channel kinetics. | 2004 Jan |
|
| Conformation of peptides in lipid membranes studied by x-ray grazing incidence scattering. | 2004 Jul |
|
| Peptaibol zervamicin IIb structure and dynamics refinement from transhydrogen bond J couplings. | 2004 Jun |
|
| Absence of NADH channeling in coupled reaction of mitochondrial malate dehydrogenase and complex I in alamethicin-permeabilized rat liver mitochondria. | 2004 Jun 11 |
|
| Real-time flow cytometry analysis of permeability transition in isolated mitochondria. | 2004 Mar 10 |
|
| Engineering charge selectivity in model ion channels. | 2004 Mar 15 |
|
| Energetics of pore formation induced by membrane active peptides. | 2004 Mar 30 |
|
| Highly robust lipid membranes on crystalline S-layer supports investigated by electrochemical impedance spectroscopy. | 2004 Mar 9 |
|
| Helical kink and channel behaviour: a comparative study with the peptaibols alamethicin, trichotoxin and antiamoebin. | 2004 May |
|
| Oxidation and reduction of pyridine nucleotides in alamethicin-permeabilized plant mitochondria. | 2004 May 15 |
|
| High-performance liquid chromatography-based methods of enzymatic analysis: electron transport chain activity in mitochondria from human skeletal muscle. | 2004 Oct 1 |
|
| The human TAZ gene complements mitochondrial dysfunction in the yeast taz1Delta mutant. Implications for Barth syndrome. | 2004 Oct 22 |
|
| Conductance studies on trichotoxin_A50E and implications for channel structure. | 2004 Sep |
|
| In vitro studies in microsomes from rat and human liver, kidney, and intestine suggest that perfluorooctanoic acid is not a substrate for microsomal UDP-glucuronosyltransferases. | 2005 |
|
| Peptaibols and related peptaibiotics of Trichoderma. A review. | 2005 |
|
| A historical overview of the heterologous expression of mammalian UDP-glucuronosyltransferase isoforms over the past twenty years. | 2005 Apr |
|
| Na,K-ATPase reconstituted in liposomes: effects of lipid composition on hydrolytic activity and enzyme orientation. | 2005 Apr 10 |
|
| Colloidal quantum dots initiating current bursts in lipid bilayers. | 2005 Apr 15 |
|
| Activation of calcium-independent phospholipase A (iPLA) in brain mitochondria and release of apoptogenic factors by BAX and truncated BID. | 2005 Aug |
|
| Alamethicin permeabilizes the plasma membrane and mitochondria but not the tonoplast in tobacco (Nicotiana tabacum L. cv Bright Yellow) suspension cells. | 2005 Aug 1 |
|
| Many-body effect of antimicrobial peptides: on the correlation between lipid's spontaneous curvature and pore formation. | 2005 Dec |
|
| Zinc ions as cytochrome C oxidase inhibitors: two sites of action. | 2005 Feb |
|
| Calcium-dependent dephosphorylation of brain mitochondrial calcium/cAMP response element binding protein (CREB). | 2005 Jan |
|
| Comparative kinetic analysis reveals that inducer-specific ion release precedes the mitochondrial permeability transition. | 2005 Jul 15 |
|
| Increased very low density lipoprotein secretion and gonadal fat mass in mice overexpressing liver DGAT1. | 2005 Jun 3 |
|
| Possible involvement of glutamic and/or aspartic acid residue(s) and requirement of mitochondrial integrity for the protective effect of creatine against inhibition of cardiac mitochondrial respiration by methylglyoxal. | 2005 Mar |
|
| Cellular and subcellular calcium accumulation during glutamate-induced injury in cerebellar granule neurons. | 2005 Mar |
|
| Impact of end-product inhibition on the determination of in vitro metabolic clearance. | 2005 May |
|
| Ca2+-induced permeabilization promotes free radical release from rat brain mitochondria with partially inhibited complex I. | 2005 May |
|
| Biotransformation of a GABAA receptor partial agonist in sprague-dawley rats and cynomolgus monkeys: identification of two unique N-carbamoyl metabolites. | 2005 Nov |
|
| Rapid collapse of mitochondrial transmembrane potential in HL-60 cells and isolated mitochondria treated with anti-tumor 1,4-anthracenediones. | 2005 Oct |
|
| Interaction of alamethicin with ether-linked phospholipid bilayers: oriented circular dichroism, 31P solid-state NMR, and differential scanning calorimetry studies. | 2005 Oct |
|
| Detection of new amino acid sequences of alamethicins F30 by nonaqueous capillary electrophoresis-mass spectrometry. | 2006 Apr |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:59:12 GMT 2025
by
admin
on
Mon Mar 31 21:59:12 GMT 2025
|
| Record UNII |
0LT1I1B7S8
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| Record Status |
Validated (UNII)
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| Record Version |
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27061-78-5
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DTXSID40893675
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0LT1I1B7S8
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76958618
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ALAMETHICIN
Created by
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