Basic information

CPKB ID	CP03521
Source	Tachypleus tridentatus [Division : Invertebrates] Taxonomy :6853 (Metazoa-Arthropoda-Xiphosura-Merostomata-Limulidae Tachypleus) Wikipedia: Tachypleus tridentatus DRAMP3
Family	Antimicrobial Peptide Tachyplesin Polyphemusin DRAMP3
Function	Anti-Bacterial Anti-Biotics Anti-Gram- Anti-Gram+ Anti-Hiv Anti-Microbial Anti-Viral DRAMP3

Legend

Structure

Molecular Formula	C99H154N34O20S4
Molecular Weight	2269.131767 g/mol
SMILES RUN SEA Predictions	CC[C@H](C)[C@@H]1NC(=O)CNC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H]2CSSC[C@H](NC1=O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@H](C(=O)N[C@@H](CCCNC(N)=[NH2+])C(N)=O)CSSC[C@H](NC(=O)[C@H](Cc1c[nH]c3ccccc13)NC(=O)[C@@H]([NH3+])CCCC[NH3+])C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](C(C)C)C(=O)N2 PDB\|1WO0
InChIKey	ZJQFYZCNRTZAIM-VNNTZLPYNA-U

2D Structure PDB\|1WO0
3D Structure PDB\|1MA2 PDB\|1MA5 PDB\|1WO0 PDB\|1WO1 PDB\|2RTV PDB\|6PIN

>>Structure Information

Beta strand •DRAMP3|DRAMP02926

>>Structure Description

This stability is due to the rigid structure imposed by the two disulfide linkages. Its amphipathic nature is closely associated with biological activity. A •DRAMP3|DRAMP02926

Sequence

One-letter code	KWCFRVCYRGICYRRCR DRAMP3\|DRAMP02926
IUPAC Condensed	LYS-TRP-CYS-PHE-ARG-VAL-CYS-TYR-ARG-GLY-ILE-CYS-TYR-ARG-ARG-CYS-ARG CyclicPepedia\|PP
Amino acid chain	LYS--TRP--CYS--PHE--ARG--VAL--CYS--TYR--ARG--GLY--ILE--CYS--TYR--ARG--ARG--CYS--ARG CyclicPepedia\|PP
Graph representation	LYS,TRP,CYS,PHE,ARG,VAL,CYS,TYR,ARG,GLY,ILE,CYS,TYR,ARG,ARG,CYS,ARG CyclicPepedia\|PP
One letter code from Structure	KWCFRVCYRGICYRRCR CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Lys--Trp--Cys(1)--Phe--Orn--Val--Cys(2)--Tyr--Orn--Gly--Ile--Cys(2)--Tyr--Orn--Orn--Cys(1)--Put CyclicPepedia\|Struct2seq
Description of the conversion sequence	The one letter code and Amino acid chain derived from the structural transformation may be inconsistent, with the Amino acid chain containing Essential Amino acid and the one letter code not.

Chemical and Physical Properties

CyclicPepedia|PP

Structure Properties

Property Name	Property Value
Exact Mass	2269.131767
Number of Rings	7.0
Complexity	0.414012739
XlogP3 AA	-16.544
Heavy Atom Count	157.0
Hydrogen Bond Donor Count	37.0
Hydrogen Bond Acceptor Count	23.0
Rotatable Bond Count	42.0

Property Name	Property Value
Formal Charge	7.0
Refractivity	591.1246
Rule_of_Five	0.0
Number of Atoms	157.0
Topological Polar Surface Area	938.42
Refractivity	591.1246
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	11000111110100100111010011110000111001100111100000011011101001001110001111101110111111000100100011110101110101001010011001110111010001011000111000011111000010010101001000111111100111001111000110110100101001001000000110000101010000000101010110001110011101101111000110001110000110101111110000000010000011010111100011010001110100000011111110111110001100000000111101001001100001000010000000101010010100000110000100001111000011110001101000110111111010100000110000010110111000011000000100001110001001010111100100101110111100011110110111001101100010001101101001010110101000100100010010000000000110111000101110010001111010011010100000111101110100111100100110110111011001000110111110111111010111001001011100010000101101100000010111010010101101001110101010110010001110101011100110011000000111001001011010011011001101011011100100001101111010110000011011111101110001110111011100110011010110000101001000000011001101100110111101110110011100110010110001011101101000011011111100010000011001010110001001110011110101000101010000111101111111110111110110001110110001001011010101001010101001100011110011000001110110001101001101001010000001101001100011101101110110000100101010011000101010110100100111001000010011111110011011000000100001001101110110100100011101110111010010011001111111000110101110001010100001111000110100001001011110111101100111010111101001001010111111010000011110010001110010110001111101001111001000000111100001011100000011100101101011001000010001111110100101001011100110111110010101110001110000111011001011010000100100100011111011100101011000110100010111110100110101101000100110100101001011010110100010000011100111001011010010100000010110100000000000100010010010001010001011000110101011100100000010110001111110000100110101000111010111101000100000100011011001011100111110010110100000001000100001111010000011110011111011101100100101110000111111100111111011000001100001010000011011101010010100001101101010010100101101000011011001010111001110010111110110100011111001011101011000001011100101100111000101111100110110011000001001101100010100000000111001000011
Morgan Fingerprint	0100000000100000010000000000010001000000001000000000010000000000110000000000000110000000001000000000000000000100000101010000000010100000000010000001000000000000000000000000000100000000000010000010010000000000000000001000100000000000000000000000000000000100000100000000000000000000001100000100001000000100000000100010000000000100100001000000000000000100000110000010100001000000000000000001010000000100011000000000000000000000000000001001010010000000000000000110000000000000000000100010000000001000000000010100010000000001100000000000000000000000000001010000000000000000000001000010000100000001100000000000000010000000001000000000000000000000000000001010000000000000010101000001000000000000010000010000000001001000010000000000001000100000100100000100000000100011000000000000001000000000000000000100000000001011000000000000000000001000100001001010100001001001001000001000000000000000000000010000010100010000000000001100010000000010000000000000000000100000001001000000000000000000100000000100000010000000000000110000000000010000
MACCS Keys	00000000000000100000000001000000000010000001000001000010000000000101000000100111001110001011100110001100111000110111011111001101111111001111111101110111111111111111110

Sequence Properties

Property Name	Property Value
Boman Index	3.53529411764705
Instability	13.2235294117647
Charge	5.74807301690143
Aliphatic Index	40.0

Manufacturers

Manufacturers Name	Value
CreativePeptides	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
Bayer healthcare pharmaceuticals	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
Upsher smith laboratories	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
Merck	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)

Manufacturers Name	Value
Apotex	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
Baxter Healthcare Corp	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
Pharmasources	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
Novartis	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
AstraZeneca	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC[C@H](C)[C@@H]1NC(=O)CNC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H]2CSSC[C@H](NC1=O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@H](C(=O)N[C@@H](CCCNC(N)=[NH2+])C(N)=O)CSSC[C@H](NC(=O)[C@H](Cc1c[nH]c3ccccc13)NC(=O)[C@@H]([NH3+])CCCC[NH3+])C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](C(C)C)C(=O)N2
Structure Properties	CC[C@H](C)[C@@H]1NC(=O)CNC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H]2CSSC[C@H](NC1=O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@H](C(=O)N[C@@H](CCCNC(N)=[NH2+])C(N)=O)CSSC[C@H](NC(=O)[C@H](Cc1c[nH]c3ccccc13)NC(=O)[C@@H]([NH3+])CCCC[NH3+])C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](C(C)C)C(=O)N2
Sequence to Structure	KWCFRVCYRGICYRRCR
Sequence Properties	KWCFRVCYRGICYRRCR
Expasy ProtParam Tool	KWCFRVCYRGICYRRCR
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	ZJQFYZCNRTZAIM-VNNTZLPYNA-U
pubchem	ZJQFYZCNRTZAIM-VNNTZLPYNA-U
Drugbank	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
DRAMP3	DRAMP02926
Uniprot	P14213
Cybase	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
CONOSERVER	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
BindingDB	CC[C@H](C)[C@@H]1NC(=O)CNC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H]2CSSC[C@H](NC1=O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@H](C(=O)N[C@@H](CCCNC(N)=[NH2+])C(N)=O)CSSC[C@H](NC(=O)[C@H](Cc1c[nH]c3ccccc13)NC(=O)[C@@H]([NH3+])CCCC[NH3+])C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=[NH2+])C(=O)N[C@@H](C(C)C)C(=O)N2
CHEMBL	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
CTD	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
Wikipedia	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
KEGG Compound/Drug	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
EPA DSSTox	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
FDA Global Substance Registration System (GSRS)	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
DTP/NCI	Tachyplesin I (Tac; Tp1; Horseshoe Crab, Arachnids, Chelicerata, Arthropods, Invertebrates)
Chemspider	ZJQFYZCNRTZAIM-VNNTZLPYNA-U

Reference

Pubmed_ID	Title	DOI	Journal
11382241	Cyclolinopeptides F-I, cyclic peptides from linseed	10.1016/s0031-9422(00)00442-8.	Phytochemistry
Cyclolinopeptides F-I, cyclic peptides from linseed Abstract Four cyclic peptides, cyclolinopeptides F-I, were isolated from seeds of Linum usitatissimum. Their structures were elucidated by extensive 2D NMR spectroscopic methods and by chemical degradation. Further, their immunosuppressive activity is examined.
12045349	New cyclic peptides from Citrus medica var. sarcodactylis SWINGLE	10.1248/cpb.50.857.	Chem Pharm Bull (Tokyo)
New cyclic peptides from Citrus medica var. sarcodactylis SWINGLE Abstract Two new cyclic peptides were isolated from the fruit peels of Citrus medica var. sarcodactylis SWINGLE. Their structures were elucidated as cyclo(-Gly-Asp-Leu-Thr-Val-Tyr-Phe-) and cyclo(-Gly-Leu-Pro-Trp-Leu-Ile-Ala-Ala-) by intensive two-dimensional (2D) NMR analysis and chemical evidence.
24408479	New flaxseed orbitides: Detection, sequencing, and (15)N incorporation	10.1002/bip.22459.	Biopolymers
New flaxseed orbitides: Detection, sequencing, and (15)N incorporation Abstract Three new orbitides (cyclolinopeptides 17, 18, and 19) were identified in flaxseed (Linum usitatissimum L.) extracts without any form of purification. Their structures were elucidated by a combination of (15) N-labeling experiments and extensive tandem mass spectrometry (MS/MS) with electrospray ionization (ESI). Putative linear peptide sequences of the new orbitides were used as the query in the Basic Local Alignment Search Tool (BLAST) searches of flax genome database. These searches returned linear sequences for the putative precursors of cyclolinopeptides 17 and 19 among others. Cyclolinopeptide 18 contains MetO (O) and is not directly encoded, but is a product of post-translation modification of the Met present in 17. The identification of precursor proteins in flax mRNA transcripts and DNA sequences confirmed the occurrence and amino acid sequences of these orbitides as [1-9-NαC]-MLKPFFFWI, [1-9-NαC]-OLKPFFFWI, and [1-9-NαC]-GIPPFWLTL for cyclolinopeptides 17, 18, and 19, respectively.