WP814   

GtoPdb Ligand ID: 8762

Compound class: Synthetic organic
Comment: WP814 is doxorubicin with the cysteinyl moiety of reduced glutathione (GSH) linked at the C-14 position [1]. WP814 potently inhibits leukotriene C4 transport via the human multidrug resistance-associated protein 1 (ABCC1) in vitro.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 14
Hydrogen bond donors 9
Rotatable bonds 16
Topological polar surface area 325.48
Molecular weight 703.17
XLogP -4.23
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
Canonical SMILES COc1cccc2c1C(=O)c1c(O)c3C(O)CC(Cc3c(c1C2=O)O)(O)C(=O)CSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
Isomeric SMILES COc1cccc2c1C(=O)c1c(O)c3[C@@H](O)C[C@](Cc3c(c1C2=O)O)(O)C(=O)CSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
InChI InChI=1S/C31H33N3O14S/c1-48-17-4-2-3-12-22(17)28(43)24-23(25(12)40)26(41)13-7-31(47,8-16(35)21(13)27(24)42)18(36)11-49-10-15(29(44)33-9-20(38)39)34-19(37)6-5-14(32)30(45)46/h2-4,14-16,35,41-42,47H,5-11,32H2,1H3,(H,33,44)(H,34,37)(H,38,39)(H,45,46)/t14-,15-,16-,31-/m0/s1
InChI Key LZWDZFWNTFSAGM-PGODJVSRSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-[2-oxo-2-[(2S,4S)-2,4,5,12-tetrahydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethyl]sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
Database Links
ChEMBL Ligand CHEMBL2074989
GtoPdb PubChem SID 252827420
PubChem CID 70682637
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