peptide ligand 2 [PMID: 19055415]   

GtoPdb Ligand ID: 8849

Compound class: Synthetic organic
Comment: Peptide ligand 2 has amino acid sequence cdGTyr(3-NO2)GBNc, where B=hydroxyproline and is represented in HELM notation by CHEMBL2372225 [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 22
Hydrogen bond donors 12
Rotatable bonds 8
Topological polar surface area 478.61
Molecular weight 885.24
XLogP -2.46
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES OC1CC2N(C1)C(=O)CNC(=O)C(NC(=O)CNC(=O)C(CC(=O)O)NC(=O)C(CSSCC(NC(=O)C(NC2=O)CC(=O)N)C(=O)N)N)Cc1ccc(c(c1)[N+](=O)[O-])O
Isomeric SMILES O[C@@H]1C[C@@H]2N(C1)C(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](CC(=O)O)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC2=O)CC(=O)N)C(=O)N)N)Cc1ccc(c(c1)[N+](=O)[O-])O
InChI InChI=1S/C32H43N11O15S2/c33-15-11-59-60-12-19(27(35)51)41-31(55)17(6-23(34)46)40-32(56)21-5-14(44)10-42(21)25(48)9-37-29(53)16(3-13-1-2-22(45)20(4-13)43(57)58)38-24(47)8-36-30(54)18(7-26(49)50)39-28(15)52/h1-2,4,14-19,21,44-45H,3,5-12,33H2,(H2,34,46)(H2,35,51)(H,36,54)(H,37,53)(H,38,47)(H,39,52)(H,40,56)(H,41,55)(H,49,50)/t14-,15+,16+,17+,18-,19+,21+/m1/s1
InChI Key VALZMCWLPCJDLL-KXXTWUBKSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-[(6S,12R,15R,20R,23S,26S,28R)-15-amino-23-(2-amino-2-oxoethyl)-20-carbamoyl-28-hydroxy-6-[(4-hydroxy-3-nitrophenyl)methyl]-2,5,8,11,14,22,25-heptaoxo-17,18-dithia-1,4,7,10,13,21,24-heptazabicyclo[24.3.0]nonacosan-12-yl]acetic acid
Database Links
GtoPdb PubChem SID 252827506
PubChem CID 73351751
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