Peptide

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Deaminooxytocin

Basic information

CPKB ID CP00911
IUPAC Name
(2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(4S,7S,10S,13S,16S)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide
Synonyms
(2S)-N-[(2S)-1-[(2-Amino-2-Oxoethyl)Amino]-4-Methyl-1-Oxopentan-2-Yl]-1-[(4S,7S,10S,13S,16S)-7-(2-Amino-2-Oxoethyl)-10-(3-Amino-3-Oxopropyl)-13-[(2S)-Butan-2-Yl]-16-[(4-Hydroxyphenyl)Methyl]-6,9,12,15,18-Pentaoxo-1,2-Dithia-5,8,11,14,17-Pentazacycloicosane-4-Carbonyl]Pyrrolidine-2-Carboxamide
113-78-0
1-Deaminooxytocin
Bdbm50056796
Chembl435716
Deaminooxytocin
Demoxytocin
Desamino-Oxytocin
Oxytocin,-Deamino-

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C43H65N11O12S2
Molecular Weight 991.4255585 g/mol
SMILES

RUN SEA Predictions

 CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)CCSSC[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O  

PubChem|13242839
InChI
InChI=1S/C43H65N11O12S2/c1-5-23(4)36-42(65)49-26(12-13-32(44)56)38(61)50-29(19-33(45)57)39(62)52-30(21-68-67-16-14-35(59)48-28(40(63)53-36)18-24-8-10-25(55)11-9-24)43(66)54-15-6-7-31(54)41(64)51-27(17-22(2)3)37(60)47-20-34(46)58/h8-11,22-23,26-31,36,55H,5-7,12-21H2,1-4H3,(H2,44,56)(H2,45,57)(H2,46,58)(H,47,60)(H,48,59)(H,49,65)(H,50,61)(H,51,64)(H,52,62)(H,53,63)/t23-,26-,27-,28-,29-,30+,31-,36-/m0/s1  
InChIKey
GTYWGUNQAMYZPF-ABSYRZPBNA-N
2D Structure
PubChem|13242839

Sequence

Graph alignment
Local alignment
IUPAC Condensed
deamino-Cys(1)-Tyr-Ile-Gln-Asn-D-Cys(1)-Pro-Leu-Gly-NH2  

PubChem|13242839
Amino acid chain
deamino--Cys(1)--Tyr--Ile--Gln--Asn--D-Cys(1)--Pro--Leu--Gly-NH2  

CyclicPepedia|PP
Graph representation
deamino,Cys,Tyr,Ile,Gln,Asn,D-Cys,Pro,Leu,Gly-NH2 @1,6  

CyclicPepedia|PP
One letter code from Structure
YIQNCPLG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Ac-Phe(1)--Ile--Gln--Asn--Cys(1)--Pro--Leu--CO  

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|13242839

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 991.4255585
Number of Rings 3.0
Complexity 0.808823529
XlogP3 AA -2.5458
Heavy Atom Count 68.0
Hydrogen Bond Donor Count 11.0
Hydrogen Bond Acceptor Count 14.0
Rotatable Bond Count 17.0
Property Name Property Value
Formal Charge 0.0
Refractivity 251.0169
Rule_of_Five 0.0
Number of Atoms 68.0
Topological Polar Surface Area 373.51
Refractivity 251.0169
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01100011101000101100100011011000110000100111110000101010100000100110101111101111101110000110110010010101000001001010011000110010010001001000110000111111000110010101001010100111100110001111100100100100101001001000000100000001010100000101011110011110011100101111000110001000000010001001100000000010011010010011101011010101010100000011111011110110101000000010011001001001100010000010000000100010000100000100100110001100000010100100101000110011111011100000100100010110111000010000000100001010001010010100100000101110110000010110101110011101100110001100100010011110101000100100010110000000000010111100101000111001101010011000100000001101100100111100001110110111011001000110001010000000010101001100011100011010101101100000000111110011001001010000101010111010001110101011001110011000000001100001001010011000001000001001110000001101111010110000011011111100010000110011011100110001010100000100111000010011001101100010111001010110011110111010010001011111101000001011111101010000011000010110001010110011010100000011010000111101001101100011110110001010100000001011010101001010101001100111110001001001110110001001001101011010000000101011100110001001110011001000111000011000101110100110100111001000010011101110111011000001100001001101110110100100011100110111010010010000101111000010001000000000100001111000110001001001011110100001000001110111101001010011111110010001011110110001010000010000100101011000001010000101110001011100100011000101101011001000010011111010001101001011101101111110110001100001110000111011011011010000100100100111010011100000001000010100110110101100110011100000101110100111001001010111100010000001000011000011000000100010110000010100000000100000010000010001001011010100100010000101000010010001011110000100110101000001010011101001100000100111011001010100110010010110100000001000100001010010000011010011111001101100100010110000011110100111110011000000100000000000100011100000010100001101101110010100101101000011010000010101001010010111110110100011111001011011001000000011001101100101000101001100110010011000001001101110000100000000011100000011
Morgan Fingerprint
0100100000100000000000000000000001000000001000000000010000000000000000000000000010000000001000000000000000000100000101000000000010100000000010010001000000000000000000000000010000000000000000000100010000000000000000000000000000000000000000000010000000000100000000000000000000000000000100000100001000000100000000100010000000000000000000000000000000000000001110000010000000000000000000000000000010000000001000000000000010000000000000001001000000000010000000001010000000100000000000100010000000001000000000010000000100000001100000000001000000001000010000010000000100000000000001000010000000000000000001000000000000000000100000001010000000000000000000000010000000000000010001000001000010001000010000000000000000000000001000000000001000100000100000000100000000100001000000010000000000000000000001000000001000001001000000000000000100001000100001000100001001000000000000000000000000100000000000000000010000010000000000000010000000000010000000010000000000000000000001000000000000000000000000000000000000000000000010000000000000010000
MACCS Keys
00000000000000100000000000000000000010000000000000000110000000000001000000110001101111001011100111001000100000110111011011101001110110001111111100111111111111111111110

Sequence Properties

Property Name Property Value
Boman Index 0.0324999999999999
Instability 29.225
Charge -0.0648408307509237
Aliphatic Index 97.5

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 GTYWGUNQAMYZPF-ABSYRZPBNA-N
pubchem 13242839
Drugbank
DRAMP3
Uniprot
Cybase
CONOSERVER
BindingDB BDBM50056796
CHEMBL CHEMBL435716
CTD
Wikipedia Demoxytocin
KEGG Compound/Drug
CHEBI GTYWGUNQAMYZPF-ABSYRZPBNA-N
EPA DSSTox
FDA Global Substance Registration System (GSRS)
DTP/NCI
Chemspider GTYWGUNQAMYZPF-ABSYRZPBNA-N

Reference

Pubmed_ID Title DOI Journal

22152977

 Lyngbyaureidamides A and B, two anabaenopeptins from the cultured freshwater cyanobacterium Lyngbya sp. (SAG 36.91) 10.1016/j.phytochem.2011.09.017.

Phytochemistry

Lyngbyaureidamides A and B, two anabaenopeptins from the cultured freshwater cyanobacterium Lyngbya sp. (SAG 36.91)

Abstract

  • Two anabaenopeptin-type peptides, lyngbyaureidamides A and B, together with two previously reported peptides lyngbyazothrins C and D, were isolated from the cultured freshwater cyanobacterium Lyngbya sp. (SAG 36.91). Their structures were determined by spectroscopic and chemical methods. Lyngbyazothrins C and D were also able to inhibit the 20S proteasome with IC(50) values of 7.1 μM and 19.2 μM, respectively, while lyngbyaureidamides A and B were not active at 50 μM.