General Information


DRAVP ID  DRAVPe02126

Peptide Name   Mirabamide G

Sequence  XYXTAGXAXLXPXQXKXVXGX

Sequence Length  11

UniProt ID  None  

Taxon ID  None 

Source   sponge Stelletta clavosa

Validation   Experimentally Validated



Origin Information


Gene Name/ID  Not Available

GenBank  Not Available

Amino Acid position  Not Available

Domain Accession ID  Not Available

Nucleotide sequence ID  Not Available

Molecular Type  Not Available

Chromosomal Position  Not Available



Activity Information


Target Organism  HIV-1

Assay  Neutralization Assays.

Activity 

  • [Ref:21280591]HIV-1:IC50=68±13μM

Hemolytic Activity  No hemolysis information or data found in the reference(s) presented in this entry

Cytotoxicity  No cytotoxicity information found in the reference(s) presented

Binding Target  Glycoprotein.

Mechanism  The mechanism of action for peptides E through H likely involves their amphipathic and cyclic nature, which enables them to interact with both viral and host cell components to inhibit HIV-1 infection. These peptides may target the HIV-1 envelope glycoproteins, such as gp120 and gp41, which are critical for viral entry into host cells. By binding to gp120, they could block its interaction with the CD4 receptor or CCR5/CXCR4 co-receptors, preventing viral attachment. Additionally, interference with gp41 could disrupt the membrane fusion process required for viral entry. Their structural properties also suggest potential interactions with the host cell membrane, altering its lipid microdomains and impeding the fusion process. Furthermore, these peptides might inhibit the HIV-1 reverse transcriptase enzyme, blocking viral RNA to DNA transcription, or interact with viral assembly proteins to disrupt the formation of infectious virions. The exact mechanism for each peptide requires further investigation, including binding studies and structural analyses, to elucidate their precise targets and pathways of action.



Structure Information


PDB ID  None

Predicted Structure Download  No predicted structure available

Linear/Cyclic  Cyclic

N-terminal Modification  The N-terminal is blocked by the Dhtda-like moiety,

C-terminal Modification  Free

Other Modification  X at position 1 is β-O-methyltyrosine (β-OMeTyr).X at position 2 is N-methylthreonine (NMeThr).X at position 5 is 3-O-methylalanine (3-OMeAla).X at position 6 is 3-hydroxyleucine (3-OHLeu).X at position 7 is 4 chlorohydroxyproline (4-ClHpr).X at position 8 is 3,4-dimethylglutamine (3,4-DiMeGln).X at position 9 is diaminobutyric acid (Dab).X at position 10 is aminobutyric acid (Aba)

Stereochemistry  L



Physicochemical Information


Formula  C66H103ClN13O20

Absent amino acids  RNDCEIMFSWOU

Common amino acids  A

Mass  1104.27

Pl  8.59

Basic residues  1

Acidic residues  0

Hydrophobic residues  6

Net charge  1

Boman Index  0.92

Hydrophobicity  -0.018

Aliphatic Index  80

Half Life 

  •     Mammalian:2.8 hours
  •     Yeast:10 min
  •     E.coli:2 min

Extinction Coefficient cystines  1490

Absorbance 280nm  1.349

Polar residues  6



Literature Information


Literature 1

Title   Mirabamides E-H, HIV-Inhibitory Depsipeptides from the Sponge Stelletta clavosa

Pubmed ID   21280591

Reference   J Nat Prod. 2011 Feb 25;74(2):185-93.

Author   Lu Z, Van Wagoner RM, Harper MK, Baker HL, Hooper JN, Bewley CA, Ireland CM.

DOI   10.1021/np100613p