Basic information

CPKB ID	CP02811
Source	Bos taurus [Division : Mammals] Taxonomy :9913 (Metazoa-Chordata-Artiodactyla-Mammalia-Bovidae Bos) Wikipedia: Bos taurus DRAMP3
Family	Cathelicidin DRAMP3
Function	Anti-Bacterial Anti-Biotics Anti-Gram- Anti-Gram+ Anti-Microbial DRAMP3
Information	Activity: Active against B. megatherium Bml 1 (MIC 11 uM), B. subtilis Bs11 (MIC 17 uM), and M. luteus Mill (MIC 20 uM) (provided by Chunfeng Wang). A S-S bond led to a CYCLIC DODECAPEPTIDE, which is more active against gram- bacteria. Derivative: Only linearized versions of the peptides (Bac2A, obtained by converting the two Cys residues to Ala residues, plus C-terminal amidation) showed activtiy against Gram+ bacteria such as S. epidermidis and E. facaelis. The linearized or reduced forms appeared to be more effective in dissipating the membrane potential (Wu M and Hancock,RE 1999 JBC 274: 29-35). MOA: Like NaD1, Bac2A is unable to disrupt SUVs and interacts with intracellular targets yet to be identified (van der Weerden et al. 2010 JBC 285:37513-20). Synergy: This peptide displayed synergistic effects with indolicidin (entry 150) against E. coli (Yan H & Hancock REW 2001 Antimicrob Agents Chemother 45: 1558-60). IDR-1018 has wound healing capability. APD APD3\|AP00008 DRAMP3\|DRAMP02851 Uniprot\|P22226

Legend

Structure

Molecular Formula	C63H120N24O13S2
Molecular Weight	1466.88024721599 g/mol
SMILES RUN SEA Predictions	CC[C@H](C)[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC1=O CyclicPepedia\|Seq2Struc
InChIKey	OAKDWMVSFFDCEY-MWCCLFPQNA-N

2D Structure CyclicPepedia\|Seq2Struc

Sequence

One-letter code	RLCRIVVIRVCR DRAMP3\|DRAMP02851
IUPAC Condensed	ARG-LEU-CYS-ARG-ILE-VAL-VAL-ILE-ARG-VAL-CYS-ARG CyclicPepedia\|PP
Amino acid chain	ARG--LEU--CYS--ARG--ILE--VAL--VAL--ILE--ARG--VAL--CYS--ARG CyclicPepedia\|PP
Graph representation	ARG,LEU,CYS,ARG,ILE,VAL,VAL,ILE,ARG,VAL,CYS,ARG CyclicPepedia\|PP

Chemical and Physical Properties

CyclicPepedia|PP

Structure Properties

Property Name	Property Value
Exact Mass	1466.88024721599
Number of Rings	1.0
Complexity	0.326732673267326
XlogP3 AA	-4.16341999999998
Heavy Atom Count	101.0
Hydrogen Bond Donor Count	26.0
Hydrogen Bond Acceptor Count	18.0
Rotatable Bond Count	27.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	390.3566
Rule_of_Five	0.0
Number of Atoms	101.0
Topological Polar Surface Area	596.8
Refractivity	390.3566
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000001001000100000000000010000110001000011000000000010000000100100000000101100101000000000100000010100000001001000011000110000010000000000110000011101000010010101001000000100000110000110000110000100001001001000000100000100010000000100010110000010011100001011000100001000000010001001100000000000000010010011100011000000010100000001001010010000000000000000001001001001100000000010000000000010000100000000000110001100000011100000000000100001101000100000000000000010011000000000000000001010000000010100100000100100110000010000001011000101000000000000101000000100001000100100010010000000000010110000100000000001011010011000000000001001000100101000000110100011001000000110000000000000010101000000011100000010001001100000010111010010001000000000001000001010001100100001100000011000000001000001001000011000001001001000000000000100110000010000000010010100000000000011000000100000000100000000001000000001000100000000001001010110011010010000000001011100101000001000011000010000011000010000001010000010010100000000010000000000001000000010100100000010100000000010010100000010001001100011110010000001110010001001000001001010000000100000100010001001010110000000001010001000101010100000100101000000010001001110000010000000100001000100100110100100011100010110010010000000110110000010001000000000100001101000000000001001010110100000000000000111100000000000110000010000010000010001010000010000100100010000001000000001000001011100000010000001101011000000010000001010000000001011100100011100010001100000100000011001001010000000100100000010010001100000001000110000000100100000010001101000000100000001001001000110000010000000000001000001000000000000010000000000000000000000010000000000000010000100000010000000000000010000011100000100110000000011000011000000100000100011001000000000110100010000100000001000000000010010000001010001111001000100000000010000011001000110010000000000000000000000000000100000010100001001101010000100101101000000010000010101000010000110010110000010110001001000000000000011000000100001000101000000110000000000001001101000000100000000000000000011
Morgan Fingerprint	0100000000100000000000000000000001000000001000000000000000000000000000000000000010000000001000000000000000000100000100000000000010100000000010000001000000000000000000000000000000000000000000000000010000000000000000001000000000000100000000000000000000000100000000000000000000000000000100000000001000000100000000000010000001000001000000010000000000000100000110000000000000000000000000000000000000000000000000000000000000000000000100000001000000000000000000000000000000000000000000000010000000001000000000000000000000000001100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000010000000000000010101000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000001000000000000000100000000100000000000000000001000000000000000000000000000000000010000001000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000100000000000000100000000000010000
MACCS Keys	00000000000000000000000001000000000000000001000000000110000000000000000000100111001010001011100100001000101000110011011111000001000100001110111100110111011110111100110

Sequence Properties

Property Name	Property Value
Boman Index	2.52
Instability	2.09166666666666
Charge	3.87402162234103
Aliphatic Index	169.999999999999

Manufacturers

Manufacturers Name	Value
CreativePeptides	Bactenecin
Bayer healthcare pharmaceuticals	Bactenecin
Upsher smith laboratories	Bactenecin
Merck	Bactenecin

Manufacturers Name	Value
Apotex	Bactenecin
Baxter Healthcare Corp	Bactenecin
Pharmasources	Bactenecin
Novartis	Bactenecin
AstraZeneca	Bactenecin

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC[C@H](C)[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC1=O
Structure Properties	CC[C@H](C)[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC1=O
Sequence to Structure	RLCRIVVIRVCR
Sequence Properties	RLCRIVVIRVCR
Expasy ProtParam Tool	RLCRIVVIRVCR
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	OAKDWMVSFFDCEY-MWCCLFPQNA-N
pubchem	OAKDWMVSFFDCEY-MWCCLFPQNA-N
Drugbank	Bactenecin
APD3	AP00008
DRAMP3	DRAMP02851
Uniprot	P22226
Cybase	Bactenecin
CONOSERVER	Bactenecin
BindingDB	CC[C@H](C)[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC1=O
CHEMBL	Bactenecin
CTD	Bactenecin
Wikipedia	Bactenecin
KEGG Compound/Drug	Bactenecin
EPA DSSTox	Bactenecin
FDA Global Substance Registration System (GSRS)	Bactenecin
DTP/NCI	Bactenecin
Chemspider	OAKDWMVSFFDCEY-MWCCLFPQNA-N

Reference

Pubmed_ID

Title

DOI

Journal

10479320

New geodiamolides from the sponge Cymbastela sp. collected in Papua New Guinea

10.1021/np990155o.

J Nat Prod

New geodiamolides from the sponge Cymbastela sp. collected in Papua New Guinea

Abstract

Geodiamolides J-P (11-17) and R (19), eight new cyclic depsipetides, have been isolated from the marine sponge Cymbastela sp. collected in Papua New Guinea. The serine residue in geodiamolides L-P (13-17) and R (19) has not been previously found in this family of compounds.