Basic information

CPKB ID	CP00140
IUPAC Name	(6S,12S,18S,21S)-15-[(2S)-butan-2-yl]-6-[(4-hydroxyphenyl)methyl]-12,18-bis(2-methylpropyl)-1,4,7,10,13,16,19-heptazabicyclo[19.3.0]tetracosane-2,5,8,11,14,17,20-heptone
Synonyms	(6S,12S,18S,21S)-15-[(2S)-Butan-2-Yl]-6-[(4-Hydroxyphenyl)Methyl]-12,18-Bis(2-Methylpropyl)-1,4,7,10,13,16,19-Heptazabicyclo[19.3.0]Tetracosane-2,5,8,11,14,17,20-Heptone 158335-65-0 4-Bromobenzylmercaptane 6-(Butan-2-Yl)-1,4,7,10,13,16-Hexahydroxy-15-[(4-Hydroxyphenyl)Methyl]-3,9-Bis(2-Methylpropyl)-3,6,9,12,15,18,21,22,23,23A-Decahydro-19H-Pyrrolo[1,2-A][1,4,7,10,13,16,19]Heptaazacyclohenicosin-19-One A4289 Cyclo(Gly-Pro-Leu-Ile-Leu-Gly-Tyr) Dtxsid20935906 Pseudostellarin-D
Source	Pseudostellaria heterophylla [Division : Plants and Fungi] Taxonomy :418402 (Viridiplantae-Streptophyta-Caryophyllales-Magnoliopsida-Caryophyllaceae Pseudostellaria) Wikipedia: Pseudostellaria heterophylla PubChem
Family	Orbitide Cybase
Information	Pseudostellarin D is a natural product found in Pseudostellaria heterophylla with data available. PubChem\|164508 Cybase\|720

Legend

Structure

Molecular Formula	C36H55N7O8
Molecular Weight	713.4112117 g/mol
SMILES RUN SEA Predictions	CC[C@H](C)C1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)CNC(=O)[C@H](CC(C)C)NC1=O PubChem\|164508
InChI	InChI=1S/C36H55N7O8/c1-7-22(6)31-36(51)41-25(15-20(2)3)32(47)37-18-29(45)39-27(17-23-10-12-24(44)13-11-23)33(48)38-19-30(46)43-14-8-9-28(43)35(50)40-26(16-21(4)5)34(49)42-31/h10-13,20-22,25-28,31,44H,7-9,14-19H2,1-6H3,(H,37,47)(H,38,48)(H,39,45)(H,40,50)(H,41,51)(H,42,49)/t22-,25-,26-,27-,28-,31?/m0/s1
InChIKey	AEYSUFUZZXZLEV-VSIRUYGUNA-N

2D Structure PubChem\|164508

Sequence

One-letter code	PLILGYG Cybase\|720
IUPAC Condensed	cyclo[Gly-Pro-Leu-DL-Ile-Leu-Gly-Tyr] PubChem\|164508
Amino acid chain	Gly(1)--Pro--Leu--DL-Ile--Leu--Gly--Tyr(1) CyclicPepedia\|PP
Graph representation	Gly,Pro,Leu,DL-Ile,Leu,Gly,Tyr @0,6 CyclicPepedia\|PP
One letter code from Structure	YGPLILG CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Ile(1)--Leu--Gly--Tyr--Gly--Pro--Leu(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\|164508

Chemical and Physical Properties

CyclicPepedia|PP

Structure Properties

Property Name	Property Value
Exact Mass	713.4112117
Number of Rings	3.0
Complexity	0.705882353
XlogP3 AA	0.2492
Heavy Atom Count	51.0
Hydrogen Bond Donor Count	7.0
Hydrogen Bond Acceptor Count	8.0
Rotatable Bond Count	8.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	188.653
Rule_of_Five	0.0
Number of Atoms	51.0
Topological Polar Surface Area	215.14
Refractivity	188.653
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000011101000100100100011011000010000100111010000101010000000100010101111101100100110000010110010000101000001001010001000110010010001001000110000011111000110010100001000100110100110000110100100100100101001001000000000000000010100000101010110001110011100101111000110001000000010001001100000000010010010010010101011000001010100000010111011010110101000000010011001000001000010000000000000000010010100000100000110001100000010000000101000110011111011100000000100010110111000010000000000001010001010010100100000101100110000000100101010010101100010000100100010010110001000000100010010000000000010111000101000110001101010011000100000001001100100111100000010100110000001000110001010000000000101001100011100010010100101100000000100100011001001011000100010001010001110101010001110010000000001100001001010001000001000001000100000001001111010110000010011101101010000110010011100100001010100000100111000000011001101000010111001010110011110011010000001011110101000001010011101010000011000010100001010000001010100000000010000101101001101110011110110001010100000001010010000001010101001100001010001001001110110001001001101010010000000101000000110001001010000000000101000001000101110100110100111001000010010001110000001000000100001001101010110100000011100110111010010010000100101000010001000000000100000110000110001001001011110100001000001100111100001000011111110000000010100110001010000010000100101011000001000000101100001011100000001000101100011001000010011111010001101001011000100000110010000100001110000111011011001000000100100100111000001100000001000010000010110100100010010100000000110100111001001010101000010000001000011000001000000100000110000000100000000100000010000000001000011000100100010000101000010010001011110000100100101000001010111001000100000100011011001010100010010010110100000000000100001010010000000000011111001101100000000010000011110100111110011000000100000000000100011100000010000001101101100000100101101000001010000010101000010000111110110000011011001011011001000000011001001100110000101000000100010010000000001101110000100000000111000000011
Morgan Fingerprint	0100100000100000000100000000000001000000001000000000000000000000000000000000000010000000001000000000000000000100000100000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000000000000100001100001000000100000000100010000001000000000000010000100000000000000010000000000000000000000000000000000000000000000000000000000000001000000000001001000010000010000000001010000000000000000000000010000000001000000000010000000000000001100000000000000000000000000000010000000000000000000000000010000000000000000000000000000000000000000000000000000000100000000000000010000000000000010001000000000000001000000001100000000000000000000000000000001000100000000000000100000000100010000000000000100000000000000000000000001000000001000000000000000100000000000000000010000001001000000000000000000000000000000000000000000100000000000000000000000000000010000000010000000000000000001001000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000010000000000000000000100001001101000011100110001000110000110111011011100001110110001111111100111111111111111111110

Sequence Properties

Property Name	Property Value
Boman Index	-2.35714285714285
Instability	11.8285714285714
Charge	-0.00286611482556564
Aliphatic Index	167.142857142857

Manufacturers

Manufacturers Name	Value
CreativePeptides	Pseudostellarin D
Bayer healthcare pharmaceuticals	Pseudostellarin D
Upsher smith laboratories	Pseudostellarin D
Merck	Pseudostellarin D

Manufacturers Name	Value
Apotex	Pseudostellarin D
Baxter Healthcare Corp	Pseudostellarin D
Pharmasources	Pseudostellarin D
Novartis	Pseudostellarin D
AstraZeneca	Pseudostellarin D

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC[C@H](C)C1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)CNC(=O)[C@H](CC(C)C)NC1=O
Structure Properties	CC[C@H](C)C1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)CNC(=O)[C@H](CC(C)C)NC1=O
Sequence to Structure	PLILGYG
Sequence Properties	PLILGYG
Expasy ProtParam Tool	PLILGYG
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	AEYSUFUZZXZLEV-VSIRUYGUNA-N
pubchem	164508
Drugbank	Pseudostellarin D
DRAMP3	Pseudostellarin D
Uniprot	Pseudostellarin D
Cybase	720
CONOSERVER	Pseudostellarin D
BindingDB	CC[C@H](C)C1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)CNC(=O)[C@H](CC(C)C)NC1=O
CHEMBL	Pseudostellarin D
CTD	Pseudostellarin D
Wikipedia	Pseudostellarin D
KEGG Compound/Drug	Pseudostellarin D
CHEBI	AEYSUFUZZXZLEV-VSIRUYGUNA-N
EPA DSSTox	DTXSID20935906
FDA Global Substance Registration System (GSRS)	Pseudostellarin D
DTP/NCI	Pseudostellarin D
Chemspider	AEYSUFUZZXZLEV-VSIRUYGUNA-N

Reference

Pubmed_ID	Title	DOI	Journal
3699982	Calcium binding cyclic hexapeptide. Crystal structure of cyclo-(L-prolyl-glycyl)3 calcium complex	None	Int J Pept Protein Res
Calcium binding cyclic hexapeptide. Crystal structure of cyclo-(L-prolyl-glycyl)3 calcium complex Abstract The synthetic cyclic hexapeptide (L-prolyl-glycyl)3 forms a 2:1 complex with Ca2+ ion. The cation is sandwiched between the two peptide molecules. The glycyl carbonyls from each of the peptides are octahedrally coordinated to the cation with an average calcium oxygen coordination distance of 2.26A. Both the molecules coordinating to the calcium ion have three fold symmetry, but show significant conformational differences. In one of the peptides of the sandwich, the alternate carbonyls point to the opposite sides of the peptide ring while in the other, all the six carbonyls point to the same side of the ring. Three NH ... O hydrogen bonds between the peptides add to the stability of the sandwich.
3814247	Crystal and molecular structure of cyclo(L-prolyl-glycyl)3. A cyclic hexapeptide with a cis peptide bond	10.1111/j.1399-3011.1986.tb01799.x.	Int J Pept Protein Res
Crystal and molecular structure of cyclo(L-prolyl-glycyl)3. A cyclic hexapeptide with a cis peptide bond Abstract The crystal structure of cyclo(L-Pro-Gly)3 was solved using X-ray crystallographic techniques. The backbone of the peptide is asymmetric and is made up of five trans peptide units and one cis peptide. There is a hydrogen bonded water bridge that links the carbonyl oxygens, O1 and O4. The molecules exist as dimers in the crystal lattice. The two molecules of the dimer are related by crystallographic twofold symmetry and are linked by two N-H ... O hydrogen bonds. The crystals are trigonal, space group P3(2)12 with a = 11.379(3), c = 32.93(1) and z = 6. The structure was solved by multisolution methods and refined by least squares technique to an R of 0.083.
7378373	Cyclo(L-prolylglycyl)3 and its sodium, potassium, and calcium ion complexes: a Raman spectroscopic study	10.1021/bi00550a012.	Biochemistry
Cyclo(L-prolylglycyl)3 and its sodium, potassium, and calcium ion complexes: a Raman spectroscopic study Abstract Raman spectra of the cyclic hexapeptide cyclo-(L-prolylglycyl)3 and its Na+, K+, and Ca2+ complexes are reported for the solid state and for samples in solution. Model compounds and N-deuteration were used to aid mode identification. Spectra of the uncomplexed ionophore in solution are consistent with previously proposed solution conformations and permit the identification of spectral lines characteristic of proline-containing peptide bonds in the trans and the cis conformations. Upon cation complexation the prolyl carbonyl stretch bands sharpen and upshift 20-30 cm-1 (to 1690-1700 cm-1). The glycyl carbonyl stretch band is unaffected by Na+ complexation, upshifted approximately 15 cm-1 by K+ complexation, and downshifted approximately 20 cm-1 (to 1619 cm-1) by Ca2+ complexation. Arguments supporting the involvement of prolyl carbonyl groups in cation complexation are noted. Spectra of the Na+ complex of the tetramer cyclo(L-prolylglycyl)4 suggest an asymmetric structure.
8075383	Crystal structure of cyclo(Pro-Gly)3:Li complex: a model for ion transport by cyclo(Pro-Gly)3	10.1002/bip.360340804.	Biopolymers
Crystal structure of cyclo(Pro-Gly)3:Li complex: a model for ion transport by cyclo(Pro-Gly)3 Abstract The crystal structure of cyclo(Pro-Gly)3 (PG3) complex with LiSCN (C22H30N7O6SLi) has been solved by x-ray diffraction. The crystals belong to the space group R3 in the hexagonal setting with unit cell parameters of a = 12.581(1), c = 29.705(3) A, V = 4072.0 A3, Z = 6, M(r) = 527.53, Dc = 1.23 g/cm3. The crystal structure was solved by direct methods using the program SHELXS-86 and refined to an R value of 5.3% for 1645 reflections (I > 2 sigma I). There are two conformers in the crystal structure. One conformer has three carbonyls on one side and three on the other side of the peptide plane. The other conformer has all six of the carbonyls on the same side of the peptide plane. Both of these conformers bind independently to a Li ion. Based on the conformers of the Li complex and other reported ion complexes formed by PG3, we propose a model for the transport of ions across the lipid membrane. The features of the model are as follows: (1) PG3 forms a hexameric stack in a lipid bilayer when complexing and transporting metal ions. (2) It undergoes a conformational flipping in order pass the ion along the channel. The energy required for the conformational change involved in the flipping of the PG3 molecule may be provided by the applied potential during ion transport.