Basic information

CPKB ID	CP03156
Source	Lactiplantibacillus plantarum [Division : Bacteria] Taxonomy :1590 (Unassigned-Bacillota-Lactobacillales-Bacilli-Lactobacillaceae Lactiplantibacillus) Wikipedia: Lactiplantibacillus plantarum DRAMP3
Family	Bacterial Class I Bacteriocin DRAMP3
Function	Anti-Bacterial Anti-Gram+ Anti-Microbial DRAMP3

Legend

Structure

Molecular Formula	C136H208N42O43S5
Molecular Weight	3259.387833632 g/mol
SMILES RUN SEA Predictions	CC[C@H](C)[C@@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CS)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC1=O CyclicPepedia\|Seq2Struc
InChIKey	CUHYCILZCOLLNF-ZLTLOQGVNA-N

2D Structure CyclicPepedia\|Seq2Struc

Sequence

One-letter code	KCKWWNISCDLGNNGHVCTLSHECQVSCN DRAMP3\|DRAMP00010
IUPAC Condensed	LYS-CYS-LYS-TRP-TRP-ASN-ILE-SER-CYS-ASP-LEU-GLY-ASN-ASN-GLY-HIS-VAL-CYS-THR-LEU-SER-HIS-GLU-CYS-GLN-VAL-SER-CYS-ASN CyclicPepedia\|PP
Amino acid chain	LYS--CYS--LYS--TRP--TRP--ASN--ILE--SER--CYS--ASP--LEU--GLY--ASN--ASN--GLY--HIS--VAL--CYS--THR--LEU--SER--HIS--GLU--CYS--GLN--VAL--SER--CYS--ASN CyclicPepedia\|PP
Graph representation	LYS,CYS,LYS,TRP,TRP,ASN,ILE,SER,CYS,ASP,LEU,GLY,ASN,ASN,GLY,HIS,VAL,CYS,THR,LEU,SER,HIS,GLU,CYS,GLN,VAL,SER,CYS,ASN CyclicPepedia\|PP

Chemical and Physical Properties

CyclicPepedia|PP

Structure Properties

Property Name	Property Value
Exact Mass	3259.387833632
Number of Rings	7.0
Complexity	0.257777777777777
XlogP3 AA	-17.4768
Heavy Atom Count	225.0
Hydrogen Bond Donor Count	51.0
Hydrogen Bond Acceptor Count	49.0
Rotatable Bond Count	49.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	815.588700000003
Rule_of_Five	0.0
Number of Atoms	225.0
Topological Polar Surface Area	1355.84999999999
Refractivity	815.588700000003
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	11101111111100101111011011110000111000100111000001011011111001101110101101101101111111010000100011110101110101001010011001110111010001011001111100011111110010010101001000011101100111001111000101110110101001001000010110000000010001000101010110011110011111101111001110001110001110101111110000100010101011011111100111010001111100000011111110011110011100010000111101001001101011000010111101101010010101000110100110101111001010110101001001111111111010100100011000010010111000111101100000001110001101010111100100101101111101111110111110001101001110100101110001010110111101101110010111001101000110111100101110111001001010011010100000111011111100101100101111100111111011000110111110111111010111001001011100111011101101100001100111011011101101101111101010001010001110100011101110011000000111011001011010011011001100111010110100101101111011111010001111111101101001110111011100110011000110100101001000010011000101010110111101110110011110010110110001011100101010011101111000010000011001010110001111111011110101000110010000111101111111110111110111111111110001001011010101001110101101100111111001010101110110101101001111111110000001101010100011101111010011011100111001011000101010110000101111011011010011011111100011001101110101001111110111100110011111010111011110011001100111001110101110001010110001111101110100011001011110111101100111000101100001011001111111010011011110110111110010110011111101011111001010000011010101011100100011100101101011111010011011111100100001001011101110111100111101110001110010111111101011000100100100100011111011110101011001110101111111110100010111100000101100000101101011010111100010000011100111101011011010100000010110110000100000111110010010011011000011010111101011100100000100110110111110100100110101000101000111001001100000110111011001011111111110010110100010001010101001111110100011110001111111101100100101111010111110100111111011001011100001010100011111101111010100001101101010011111101101100001011011010111001111001111110110000011111001011101011011001001101001100111101101111100110110000000001011101100010100110100111101010111
Morgan Fingerprint	0100000000100000000000000000000001000000001000000000000000100000100000000000000010000000001000000000000000000100000100010100000000100000000010000001000000000000100000000000000100000000000000000000000000010000000000001000001000010100000000000000000000000100000000010000000000000000000100000000001000000100000000000010000001000101100001110000000000000100000110000000100000000000001000000000010001000000000000000000000000000000000010000001000010000000000000000010000000000000001000000010000000001100000000010000000000000001100000000000000000001000010001010000000000000000000000010000000100000000000000000000000000000000100000000100000000000000000000000010000000000000010001000000000000001001000000100100000000000000010100000010101000000010100000000000000000000011000000010000000000000000000000000000001000000011000000001000100100000000100000000010001001001001000000000000000000100000000000010000010100000000000000000100000000000010000100000000000000000000001000000000000000000000000001000000000100000010000010100000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000110000000000100000000100101101110001111100111001100110001110011011011010101110110001111111101110111111111111111110

Sequence Properties

Property Name	Property Value
Boman Index	1.55310344827586
Instability	71.2689655172413
Charge	-0.128439559219054
Aliphatic Index	60.3448275862069

Manufacturers

Manufacturers Name	Value
CreativePeptides	Plantaricin W Alpha
Bayer healthcare pharmaceuticals	Plantaricin W Alpha
Upsher smith laboratories	Plantaricin W Alpha
Merck	Plantaricin W Alpha

Manufacturers Name	Value
Apotex	Plantaricin W Alpha
Baxter Healthcare Corp	Plantaricin W Alpha
Pharmasources	Plantaricin W Alpha
Novartis	Plantaricin W Alpha
AstraZeneca	Plantaricin W Alpha

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC[C@H](C)[C@@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CS)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC1=O
Structure Properties	CC[C@H](C)[C@@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CS)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC1=O
Sequence to Structure	KCKWWNISCDLGNNGHVCTLSHECQVSCN
Sequence Properties	KCKWWNISCDLGNNGHVCTLSHECQVSCN
Expasy ProtParam Tool	KCKWWNISCDLGNNGHVCTLSHECQVSCN
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	CUHYCILZCOLLNF-ZLTLOQGVNA-N
pubchem	CUHYCILZCOLLNF-ZLTLOQGVNA-N
Drugbank	Plantaricin W Alpha
DRAMP3	DRAMP00010
Uniprot	D2KR94
Cybase	Plantaricin W Alpha
CONOSERVER	Plantaricin W Alpha
BindingDB	CC[C@H](C)[C@@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CS)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC1=O
CHEMBL	Plantaricin W Alpha
CTD	Plantaricin W Alpha
Wikipedia	Plantaricin W Alpha
KEGG Compound/Drug	Plantaricin W Alpha
EPA DSSTox	Plantaricin W Alpha
FDA Global Substance Registration System (GSRS)	Plantaricin W Alpha
DTP/NCI	Plantaricin W Alpha
Chemspider	CUHYCILZCOLLNF-ZLTLOQGVNA-N

Reference

Pubmed_ID	Title	DOI	Journal
21554452	The biosynthesis of Caryophyllaceae-like cyclic peptides in Saponaria vaccaria L. from DNA-encoded precursors	10.1111/j.1365-313X.2011.04626.x.	Plant J
The biosynthesis of Caryophyllaceae-like cyclic peptides in Saponaria vaccaria L. from DNA-encoded precursors Abstract Cyclic peptides (CPs) are produced in a very wide range of taxa. Their biosynthesis generally involves either non-ribosomal peptide synthases or ribosome-dependent production of precursor peptides. Plants within the Caryophyllaceae and certain other families produce CPs which generally consist of 5-9 proteinogenic amino acids. The biological roles for these CPs in the plant are not very clear, but many of them have activity in mammalian systems. There is currently very little known about the biosynthesis of CPs in the Caryophyllaceae. A collection of expressed sequence tags from developing seeds of Saponaria vaccaria was investigated for information about CP biosynthesis. This revealed genes that appeared to encode CP precursors which are subsequently cyclized to mature CPs. This was tested and confirmed by the expression of a cDNA encoding a putative precursor of the CP segetalin A in transformed S. vaccaria roots. Similarly, extracts of developing S. vaccaria seeds were shown to catalyze the production of segetalin A from the same putative (synthetic) precursor. Moreover, the presence in S. vaccaria seeds of two segetalins, J [cyclo(FGTHGLPAP)] and K [cyclo(GRVKA)], which was predicted by sequence analysis, was confirmed by liquid chromatography/mass spectrometry. Sequence analysis also predicts the presence of similar CP precursor genes in Dianthus caryophyllus and Citrus spp. The data support the ribosome-dependent biosynthesis of Caryophyllaceae-like CPs in the Caryophyllaceae and Rutaceae.

Pubmed_ID

Title

DOI

Journal

21554452

The biosynthesis of Caryophyllaceae-like cyclic peptides in Saponaria vaccaria L. from DNA-encoded precursors

10.1111/j.1365-313X.2011.04626.x.

Plant J

The biosynthesis of Caryophyllaceae-like cyclic peptides in Saponaria vaccaria L. from DNA-encoded precursors

Abstract

Cyclic peptides (CPs) are produced in a very wide range of taxa. Their biosynthesis generally involves either non-ribosomal peptide synthases or ribosome-dependent production of precursor peptides. Plants within the Caryophyllaceae and certain other families produce CPs which generally consist of 5-9 proteinogenic amino acids. The biological roles for these CPs in the plant are not very clear, but many of them have activity in mammalian systems. There is currently very little known about the biosynthesis of CPs in the Caryophyllaceae. A collection of expressed sequence tags from developing seeds of Saponaria vaccaria was investigated for information about CP biosynthesis. This revealed genes that appeared to encode CP precursors which are subsequently cyclized to mature CPs. This was tested and confirmed by the expression of a cDNA encoding a putative precursor of the CP segetalin A in transformed S. vaccaria roots. Similarly, extracts of developing S. vaccaria seeds were shown to catalyze the production of segetalin A from the same putative (synthetic) precursor. Moreover, the presence in S. vaccaria seeds of two segetalins, J [cyclo(FGTHGLPAP)] and K [cyclo(GRVKA)], which was predicted by sequence analysis, was confirmed by liquid chromatography/mass spectrometry. Sequence analysis also predicts the presence of similar CP precursor genes in Dianthus caryophyllus and Citrus spp. The data support the ribosome-dependent biosynthesis of Caryophyllaceae-like CPs in the Caryophyllaceae and Rutaceae.

Plantaricin W Alpha

Basic information

Legend

Structure

Download structure

Sequence

Chemical and Physical Properties

Structure Properties

Sequence Properties

Manufacturers

Forecasting tools

Information Source

Reference

The biosynthesis of Caryophyllaceae-like cyclic peptides in Saponaria vaccaria L. from DNA-encoded precursors

Abstract