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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
Structure of ALAMETHICIN

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
Ion channel are sensitive to gravity changes.
2001
Alamethicin channel conductance modified by lipid charge.
2001 Aug
Proline-induced hinges in transmembrane helices: possible roles in ion channel gating.
2001 Aug 1
Trichorzin HA V, a member of the peptaibol family, stimulates intracellular cAMP formation in cells expressing the calcitonin receptor.
2001 Dec
Quaternary ammonium-linked glucuronidation of 1-substituted imidazoles: studies of human UDP-glucuronosyltransferases involved and substrate specificities.
2001 Oct
Protein-water interactions.
2002
Detection of protein-ligand interaction on the membranes using C-terminus biotin-tagged alamethicin.
2002 Aug
Sigmoidal concentration dependence of antimicrobial peptide activities: a case study on alamethicin.
2002 Feb
Modifications of alamethicin ion channels by substitution of Glu-7 for Gln-7.
2002 Jul
Synthesis and ion conductance behavior of a tetrameric alamethicin ion channel.
2002 May 16
Histone 2A stimulates glucose-6-phosphatase activity by permeabilization of liver microsomes.
2002 Oct 15
Changes in lipid mobility associated with alamethicin incorporation into membranes.
2002 Sep 15
Photosensitizing effect of protoporphyrin IX in pigmented melanoma of mice.
2002 Sep 27
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
Ion channels of alamethicin dimer N-terminally linked by disulfide bond.
2003 Jul
The implementation of slab geometry for membrane-channel molecular dynamics simulations.
2003 Jul
Metabolic assessment in liver microsomes by co-activating cytochrome P450s and UDP-glycosyltransferases.
2003 Jul-Sep
Evidence for membrane thinning effect as the mechanism for peptide-induced pore formation.
2003 Jun
The effect of incubation conditions on the enzyme kinetics of udp-glucuronosyltransferases.
2003 Jun
Investigation of the role and mechanism of IF1 and STF1 proteins, twin inhibitory peptides which interact with the yeast mitochondrial ATP synthase.
2003 Jun 24
Understanding pH-dependent selectivity of alamethicin K18 channels by computer simulation.
2003 Mar
Characterization of an ectonucleoside triphosphate diphosphohydrolase 1 activity in alkaline phosphatase-depleted rat osseous plate membranes: possible functional involvement in the calcification process.
2003 Mar 21
N-terminal insertion of alamethicin in channel formation studied using its covalent dimer N-terminally linked by disulfide bond.
2003 May 2
Amoebapores and NK-lysin, members of a class of structurally distinct antimicrobial and cytolytic peptides from protozoa and mammals: a comparative functional analysis.
2003 Nov 1
Microfabricated teflon membranes for low-noise recordings of ion channels in planar lipid bilayers.
2003 Oct
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
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
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
The human TAZ gene complements mitochondrial dysfunction in the yeast taz1Delta mutant. Implications for Barth syndrome.
2004 Oct 22
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
A historical overview of the heterologous expression of mammalian UDP-glucuronosyltransferase isoforms over the past twenty years.
2005 Apr
Colloidal quantum dots initiating current bursts in lipid bilayers.
2005 Apr 15
Many-body effect of antimicrobial peptides: on the correlation between lipid's spontaneous curvature and pore formation.
2005 Dec
Comparative kinetic analysis reveals that inducer-specific ion release precedes the mitochondrial permeability transition.
2005 Jul 15
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
Rapid collapse of mitochondrial transmembrane potential in HL-60 cells and isolated mitochondria treated with anti-tumor 1,4-anthracenediones.
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 Thu Jul 06 13:43:32 UTC 2023
Edited
by admin
on Thu Jul 06 13:43:32 UTC 2023
Record UNII
0LT1I1B7S8
Record Status Validated (UNII)
Record Version
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Name Type Language
ALAMETHICIN
Common Name English
AC-AIB-PRO-AIB-ALA-AIB-ALA-GLN-AIB-VAL-AIB-GLY-LEU-AIB-PRO-VAL-AIB-AIB-GLU-GLN-PHL
Common Name English
Code System Code Type Description
CAS
27061-78-5
Created by admin on Thu Jul 06 13:43:32 UTC 2023 , Edited by admin on Thu Jul 06 13:43:32 UTC 2023
PRIMARY
EPA CompTox
DTXSID40893675
Created by admin on Thu Jul 06 13:43:32 UTC 2023 , Edited by admin on Thu Jul 06 13:43:32 UTC 2023
PRIMARY
FDA UNII
0LT1I1B7S8
Created by admin on Thu Jul 06 13:43:32 UTC 2023 , Edited by admin on Thu Jul 06 13:43:32 UTC 2023
PRIMARY
PUBCHEM
76958618
Created by admin on Thu Jul 06 13:43:32 UTC 2023 , Edited by admin on Thu Jul 06 13:43:32 UTC 2023
PRIMARY
WIKIPEDIA
ALAMETHICIN
Created by admin on Thu Jul 06 13:43:32 UTC 2023 , Edited by admin on Thu Jul 06 13:43:32 UTC 2023
PRIMARY