Peptide

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Cyclo[Dl-Ala-Dl-Xiile-Gly-Dl-Cys(1)-Dl-Ser-Dl-Cys(2)-Dl-Lys-Dl-Ser-Dl-Lys-Dl-Val-Dl-Cys(3)-Dl-Tyr-Dl-Arg-Dl-Asn-Gly-Dl-Xiile-Dl-Pro-Dl-Cys(1)-Gly-Dl-Glu-Dl-Ser-Dl-Cys(2)-Dl-Val-Dl-Trp-Dl-Xiile-Dl-Pro-Dl-Cys(3)-Dl-Xiile-Dl-Ser-Dl-Ser]

Basic information

CPKB ID CP02116
IUPAC Name
3-[43,49-bis(4-aminobutyl)-28-(2-amino-2-oxoethyl)-22,64,76,88-tetra(butan-2-yl)-31-(3-carbamimidamidopropyl)-4,46,55,70,73-pentakis(hydroxymethyl)-34-[(4-hydroxyphenyl)methyl]-91-(1H-indol-3-ylmethyl)-67-methyl-3,6,9,12,15,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,87,90,93,96-triacontaoxo-40,94-di(propan-2-yl)-2a,3a,6a,7a,98,99-hexathia-2,5,8,11,14,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,86,89,92,95-triacontazahexacyclo[50.44.4.413,58.437,79.016,20.082,86]octahectan-7-yl]propanoic acid
Source

Viola odorata [Division : Plants and Fungi]

Taxonomy :97441 (Viridiplantae-Streptophyta-Malpighiales-Magnoliopsida-Violaceae Viola)  

Wikipedia: Viola odorata

PubChem  

Information

Cyclo[DL-Ala-DL-xiIle-Gly-DL-Cys(1)-DL-Ser-DL-Cys(2)-DL-Lys-DL-Ser-DL-Lys-DL-Val-DL-Cys(3)-DL-Tyr-DL-Arg-DL-Asn-Gly-DL-xiIle-DL-Pro-DL-Cys(1)-Gly-DL-Glu-DL-Ser-DL-Cys(2)-DL-Val-DL-Trp-DL-xiIle-DL-Pro-DL-Cys(3)-DL-xiIle-DL-Ser-DL-Ser] is a natural product found in Viola odorata with data available.

PubChem|139033098  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C133H207N37O39S6
Molecular Weight 3138.367616 g/mol
SMILES

RUN SEA Predictions

 CCC(C)C1NC(=O)C(C)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(C(C)CC)NC(=O)C2CSSCC3NC(=O)C(C(C)C)NC(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C(CCCCN)NC(=O)C4CSSCC(NC(=O)C(CO)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)C(CSSCC(NC(=O)CNC1=O)C(=O)NC(CO)C(=O)N4)NC(=O)C1CCCN1C(=O)C(C(C)CC)NC(=O)CNC(=O)C(CC(N)=O)NC(=O)C(CCCNC(=N)N)NC(=O)C(Cc1ccc(O)cc1)NC3=O)C(=O)NC(C(C)C)C(=O)NC(Cc1c[nH]c3ccccc13)C(=O)NC(C(C)CC)C(=O)N1CCCC1C(=O)N2  

PubChem|139033098
InChI
InChI=1S/C133H207N37O39S6/c1-14-65(9)102-127(204)143-50-97(179)146-88-58-211-210-57-87-108(185)142-49-96(178)145-78(38-39-99(181)182)111(188)154-84(54-173)118(195)159-91-61-214-212-59-89(158-119(196)85(55-174)156-120(88)197)121(198)149-75(29-20-22-40-134)110(187)153-83(53-172)116(193)148-76(30-21-23-41-135)112(189)164-101(64(7)8)129(206)162-90(122(199)150-79(45-70-34-36-72(176)37-35-70)113(190)147-77(31-24-42-139-133(137)138)109(186)151-81(47-95(136)177)107(184)141-51-98(180)163-104(67(11)16-3)131(208)169-43-25-32-93(169)125(202)160-87)60-213-215-62-92(124(201)167-103(66(10)15-2)130(207)157-86(56-175)117(194)155-82(52-171)115(192)144-69(13)106(183)166-102)161-126(203)94-33-26-44-170(94)132(209)105(68(12)17-4)168-114(191)80(152-128(205)100(63(5)6)165-123(91)200)46-71-48-140-74-28-19-18-27-73(71)74/h18-19,27-28,34-37,48,63-69,75-94,100-105,140,171-176H,14-17,20-26,29-33,38-47,49-62,134-135H2,1-13H3,(H2,136,177)(H,141,184)(H,142,185)(H,143,204)(H,144,192)(H,145,178)(H,146,179)(H,147,190)(H,148,193)(H,149,198)(H,150,199)(H,151,186)(H,152,205)(H,153,187)(H,154,188)(H,155,194)(H,156,197)(H,157,207)(H,158,196)(H,159,195)(H,160,202)(H,161,203)(H,162,206)(H,163,180)(H,164,189)(H,165,200)(H,166,183)(H,167,201)(H,168,191)(H,181,182)(H4,137,138,139)  
InChIKey
LNKLNUAMTRHBLB-XGUSXARDNA-N
2D Structure
PubChem|139033098

Sequence

Graph alignment
Local alignment
IUPAC Condensed
cyclo[DL-Ala-DL-xiIle-Gly-DL-Cys(1)-DL-Ser-DL-Cys(2)-DL-Lys-DL-Ser-DL-Lys-DL-Val-DL-Cys(3)-DL-Tyr-DL-Arg-DL-Asn-Gly-DL-xiIle-DL-Pro-DL-Cys(1)-Gly-DL-Glu-DL-Ser-DL-Cys(2)-DL-Val-DL-Trp-DL-xiIle-DL-Pro-DL-Cys(3)-DL-xiIle-DL-Ser-DL-Ser]  

PubChem|139033098
Amino acid chain
DL-Ala(4)--DL-xiIle--Gly--DL-Cys(1)--DL-Ser--DL-Cys(2)--DL-Lys--DL-Ser--DL-Lys--DL-Val--DL-Cys(3)--DL-Tyr--DL-Arg--DL-Asn--Gly--DL-xiIle--DL-Pro--DL-Cys(1)--Gly--DL-Glu--DL-Ser--DL-Cys(2)--DL-Val--DL-Trp--DL-xiIle--DL-Pro--DL-Cys(3)--DL-xiIle--DL-Ser--DL-Ser(4)  

CyclicPepedia|PP
Graph representation
DL-Ala,DL-xiIle,Gly,DL-Cys,DL-Ser,DL-Cys,DL-Lys,DL-Ser,DL-Lys,DL-Val,DL-Cys,DL-Tyr,DL-Arg,DL-Asn,Gly,DL-xiIle,DL-Pro,DL-Cys,Gly,DL-Glu,DL-Ser,DL-Cys,DL-Val,DL-Trp,DL-xiIle,DL-Pro,DL-Cys,DL-xiIle,DL-Ser,DL-Ser @3,17 @5,21 @10,26 @0,29  

CyclicPepedia|PP
One letter code from Structure
ESCVWIPCISSAIGCSCKSKVCYRNGIPCG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Ile(1)--Gly--Cys(2)--Ser--Cys(3)--Lys--Ser--Lys--Val--Cys(4)--Tyr--Orn--Asn--Gly--Ile--Pro--Cys(2)--Gly--Glu--Ser--Cys(3)--Val--Trp--Ile--Pro--Cys(4)--Ile--Ser--Ser--Ala(1)  

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.
svg Image

PubChem|139033098

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 3138.367616
Number of Rings 10.0
Complexity 0.31627907
XlogP3 AA -12.95283
Heavy Atom Count 215.0
Hydrogen Bond Donor Count 42.0
Hydrogen Bond Acceptor Count 47.0
Rotatable Bond Count 36.0
Property Name Property Value
Formal Charge 0.0
Refractivity 789.5699
Rule_of_Five 0.0
Number of Atoms 215.0
Topological Polar Surface Area 1186.92
Refractivity 789.5699
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
11100111110100101111110011111000111001100111110000111011101001101110101111101111111111010110110011110111110101001010011001110111010001011100111100011111100110010101001010111111100111001111100111110110101001001000000110000101010100000101011110001110011101101111000110001110000110101111110000000010011011011111101111010001110100010011111111111110101100000010111101001001101011000010001000101010010100000110100100001111000011110101101000111111111011100000110100010110111000011000000100001110001011010111100100101110111101111110110111011101100110001101101011010110101000101110010110001001000110111100101110111001111010011010100000111111110100111100101111110111011001000110111110111111010111001101011100011000101101100000010111110011101101011111101010110010001110101011101110011000000111101001011010011011001101011011110100001101111010110000011011111101111001110111011100110011010110000101111000010011001101100110111101110110011110111110110001011111101000011011111101010000011001010110001001110011110101000111010000111101111111110111110110001111110001001011010101001110101001100011110011001001110110001101001101011010000001101011100111101101110111001100111011011000101110110110101111001001010011111110111011001000100101001101110111100110011101110111011010011001111111000110101110001110110001111000110101001001011110111101100111111111101001011011111111010001011110110011110010110001111101001111001010000111110101011100100011100101101011001000011011111110101101001011101110111110110101110001110000111111011011010000100100100111111011110101011001110100111111110100110111101000101110100111001011010111100010000011100111101011010010100010110110110100000000111010010010011011001011010110101011100101000010110001111110100100110101000111010111101001100000110111011001011101111110010110100010001000100001111110000011110011111111101100100111111010111111100111111011001011100001010000111011101010010100001101101110010110101101000011011011010111001110011111110110100011111001011111011010001011101101100111001101111100110110011000001011101110010100100000111101000011
Morgan Fingerprint
0100110000100000000100000000010001000000001000010000010000100000110000000000000010000000001000000000010000000100000100010000000010100000000010000001000000000000100000000000000100000000000000000010010000010000000000001000001000000001000000000000000000100100000000010000000000000000000101001100001000000100000000100010000000000100100001100000100000000100000110000000100000000000000000000000010001000000000000000000000000000000000100001001000010000010000000001010000000000000001000100010000000001100000000010001000000000001100000000000000000001000000001010000000000000000000000000010000100000000000000000000000000000000000000010000000000100000000000000010000000000000010101000001000000001000000000000100000000000000010000000000001000100000000000000100000000100011000000010000000000000000100000000100001000001011000000001000000000000000100000001010001001001001000010000001000000100000000000010000011100010000000000000100000000000010000000010000000000000000001001000000000000000000000101011000000000000010000010100000000000010000
MACCS Keys
00000000000000100000000001000000000010000001000000000110000000000101000000100111101111001111100111001100111001110111011111111101111110001111111101111111111111111111110

Sequence Properties

Property Name Property Value
Boman Index 0.473666666666666
Instability 22.5866666666666
Charge 1.62646733336383
Aliphatic Index 74.6666666666666

Manufacturers

Manufacturers Name Value
CreativePeptides
Bayer healthcare pharmaceuticals
Upsher smith laboratories
Merck
Manufacturers Name Value
Apotex
Baxter Healthcare Corp
Pharmasources
Novartis
AstraZeneca

Forecasting tools

Information Source

Property Name Property ID
Patents LNKLNUAMTRHBLB-XGUSXARDNA-N
pubchem 139033098
Drugbank
DRAMP3
Uniprot
Cybase
CONOSERVER
BindingDB
CHEMBL
CTD
Wikipedia
KEGG Compound/Drug
CHEBI LNKLNUAMTRHBLB-XGUSXARDNA-N
EPA DSSTox
FDA Global Substance Registration System (GSRS)
DTP/NCI
Chemspider LNKLNUAMTRHBLB-XGUSXARDNA-N

Reference

Pubmed_ID Title DOI Journal

15387654

 BI-32169, a bicyclic 19-peptide with strong glucagon receptor antagonist activity from Streptomyces sp 10.1021/np040093o.

J Nat Prod

BI-32169, a bicyclic 19-peptide with strong glucagon receptor antagonist activity from Streptomyces sp

Abstract

  • A new bicyclic 19-peptide, BI-32169, has been isolated from the culture broth of Streptomyces sp. (DSM 14996). Its structure has been established by amino acid analysis, mass spectrometry, and 2D NMR analysis. BI-32169 consists exclusively of protein amino acids and is cyclized from the side chain of Asp(9) to the N-terminus of Gly(1). One disulfide bond between Cys(6) and Cys(19) forms a bicyclic structure. BI-32169 and its methyl ester derivative showed potent inhibitory activity against the human glucagon receptor (IC(50) 440 and 320 nM, respectively) in a functional cell-based assay.