CAS 27061-78-5|(4S)-4-{[(1S)-3-carbamoyl-1-{[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamoyl}propyl]carbamoyl}-4-(2-{2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-(2-{2-[(2S)-2-{2-[(2S)-4-carbamoyl-2-[(2S)-2-{2-[(2S)-...

General Information

Structure

Molecular Formula

C₉₂H₁₅₀N₂₂O₂₅

Molecular Mass

1964.3078

Exact Mass

1963.11424841

Charge

InChI

InChI=1S/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)/t50-,51-,54+,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1

InChIKey

LGHSQOCGTJHDIL-SLKIUSOBSA-N

Canonic Smiles

OC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)C(NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1C(=O)C(NC(=O)[C@@H](NC(=O)CNC(=O)C(NC(=O)[C@H](C(C)C)NC(=O)C(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H]1CCCN1C(=O)C(NC(=O)C)(C)C)(C)C)C)(C)C)C)CCC(=O)N)(C)C)(C)C)CC(C)C)(C)C)(C)C)(C)C)CCC(=O)O)CCC(=O)N)Cc1ccccc1

Isomeric Smiles

C[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)NC(C)(C)C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@H](Cc1ccccc1)CO)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(=O)C

Calculated Properties

JChem

Acid pKa

4.0946937

H Acceptors

H Donor

LogD (pH = 5.5)

-7.242025

LogD (pH = 7.4)

-8.925522

Log P

-5.8232164

Molar Refractivity

499.6144

Polarizability

195.59917

Polar Surface Area

708.13

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC name

(4S)-4-{[(1S)-3-carbamoyl-1-{[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamoyl}propyl]carbamoyl}-4-(2-{2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-(2-{2-[(2S)-2-{2-[(2S)-4-carbamoyl-2-[(2S)-2-{2-[(2S)-2-(2-{[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl]formamido}-2-methylpropanamido)propanamido]-2-methylpropanamido}propanamido]butanamido]-2-methylpropanamido}-3-methylbutanamido]-2-methylpropanamido}acetamido)-4-methylpentanamido]-2-methylpropanoyl}pyrrolidin-2-yl]formamido}-3-methylbutanamido]-2-methylpropanamido}-2-methylpropanamido)butanoic acid

IUPAC Traditional name

Synonyms

Antibiotic U-22324Alamethicin from Trichoderma virideAlamethicin(3S,12R)-1-((S)-1-((6S,12S,15S,21S,30S)-1-((R)-1-(2-Acetamido-2-methylpropanoyl)pyrrolidin-2-yl)-15-(3-amino-3-oxopropyl)-30-isobutyl-21-isopropyl-3,3,6,9,9,2,18,18,24,24,33,33-dodecamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaoxo-2,5,8,11,14,17,20,23,26,29,32-undecaazatetratriacontan-34-oyl)pyrrolidin-2-yl)-12-(((R)-5-amino-1-(((S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1,5-dioxopentan-2-yl)carbamoyl)-3-isopropyl-6,6,9,9-tetramethyl-1,4,7,10-tetraoxo-2,5,8,11-tetraazapentadecan-15-oic Acid

Names and Identifiers

Registration numbers

PubChem SID

MDL Number

Beilstein Number

CAS Number

PubChem CID

Registration numbers

Properties

Product Information

Quality Level

PREMIUM

Purity

≥98% (HPLC)

≥50% (main component, HPLC)

Certificate of Analysis

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Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

05125

A4665

Antibody Adsorbant
Ac-2-MeAla-L-Pro-2-MeAla-L-Ala-2-MeAla-L-Ala-L-Glu(NH2)-2-MeAla-L-Val-2-MeAla-Gly-L-Leu-2-MeAla-L-Pro-L-Val-2-MeAla-2-MeAla-L-Glu-L-Glu(NH2)-phenylalaninol
Biochem/physiol Actions
Monovalent cation ionophore; can mimic nerve action potential across artificial membranes.
Quality
A mixture of alamethicin homologs
Application
Alamethicin is a monovalent cation ionophore which can mimic nerve action potential across artificial membranes. Alamethicin has also been used to study membrane interactions of antimicrobial peptides.

TRC

A470700

Alamethicin is a peptide antibiotic, produced by the fungus Trichoderma viride. Alamethicin contains the non-proteinogenic amino acid 2-aminoisobutyric acid (Aib), which strongly induces helical peptide structures. In cell membranes, it forms voltage-depe

Molecule Details

References

PubChem Literature

From Data Sources

• Almeida, P., et al.: Biochemistry, 48, 8083 (2003)

• Henriques, S., et al.: Biochem. J., 399, 1 (2003)

• Heitz, F., et al.: Br. J. Pharmacol., 157, 195 (2003)

• Afonin, S., et al.: Chembiochem., 4, 1151 (2003)

References

Bioactivity

PubChem BioAssay

Bioactivity