Peptide name : Sungsanpin

Source/Organism : Marine **Streptomyces species

Linear/Cyclic : Cyclic

Chirality : L

Peptide length: 15

C-terminal modification: Cyclic

N-terminal modification : Free

Non-natural peptide information: None

Assay type : Cell invasion assay

Assay time : 24h

Activity : MIC : 5 μM

Cell line : A549

Cancer type : Lung cancer

Other activity : Not found

Amino acid composition bar chart :

Molecular mass : 1610.8063 Dalton

Aliphatic index : 0.78

Instability index : 25.3733

Hydrophobicity (GRAVY) : 0.28

Isoelectric point : 5.8357

Charge (pH 7) : -0.2398

Aromaticity : 0.2

Molar extinction coefficient (cysteine, cystine): (5500, 5500)

Hydrophobic/hydrophilic ratio : 2

hydrophobic moment : -0.243

Missing amino acid : C,R,H,Q,T,M,E,Y,N,A,V

Most occurring amino acid : G

Most occurring amino acid frequency : 3

Least occurring amino acid : K

Least occurring amino acid frequency : 1

Secondary structure fraction (Helix, Turn, Sheet): (0.2, 0.5, 0.4)

SMILES Notation: CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)CN)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1ccccc1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(C)C)C(=O)O

1 : Um S, et al. Sungsanpin, a lasso peptide from a deep-sea streptomycete. J Nat Prod. 2013; 76:873-9. doi: 10.1021/np300902g

Paper title : Sungsanpin, a lasso peptide from a deep-sea streptomycete.

Doi : https://doi.org/10.1021/np300902g

Abstract : Sungsanpin (1), a new 15-amino-acid peptide, was discovered from a Streptomyces species isolated from deep-sea sediment collected off Jeju Island, Korea. The planar structure of 1 was determined by 1D and 2D NMR spectroscopy, mass spectrometry, and UV spectroscopy. The absolute configurations of the stereocenters in this compound were assigned by derivatizations of the hydrolysate of 1 with Marfey's reagents and 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate, followed by LC-MS analysis. Careful analysis of the ROESY NMR spectrum and three-dimensional structure calculations revealed that sungsanpin possesses the features of a lasso peptide: eight amino acids (-Gly(1)-Phe-Gly-Ser-Lys-Pro-Ile-Asp(8)-) that form a cyclic peptide and seven amino acids (-Ser(9)-Phe-Gly-Leu-Ser-Trp-Leu(15)) that form a tail that loops through the ring. Sungsanpin is thus the first example of a lasso peptide isolated from a marine-derived microorganism. Sungsanpin displayed inhibitory activity in a cell invasion assay with the human lung cancer cell line A549.