compound 9 [PMID: 15615544]   

GtoPdb Ligand ID: 8890

Compound class: Synthetic organic
Comment: Compound 9 is an analogue of aminopterin (the 4-amino derivative of folic acid; PubChem CID 2154; related to methotrexate), but with a rotationally restricted side chain amide bond. Compound 9 manifests antifolate activity in vitro, achieved by inhibiting both dihydrofolate reductase (DHFR) and folate transporter 1 (reduced folate carrier) activities [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 13
Hydrogen bond donors 5
Rotatable bonds 8
Topological polar surface area 210.54
Molecular weight 452.16
XLogP -3.4
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)CCC(N1Cc2c(C1=O)ccc(c2)NCc1cnc2c(n1)c(N)nc(n2)N)C(=O)O
Isomeric SMILES OC(=O)CC[C@H](N1Cc2c(C1=O)ccc(c2)NCc1cnc2c(n1)c(N)nc(n2)N)C(=O)O
InChI InChI=1S/C20H20N8O5/c21-16-15-17(27-20(22)26-16)24-7-11(25-15)6-23-10-1-2-12-9(5-10)8-28(18(12)31)13(19(32)33)3-4-14(29)30/h1-2,5,7,13,23H,3-4,6,8H2,(H,29,30)(H,32,33)(H4,21,22,24,26,27)/t13-/m0/s1
InChI Key NYPQVENKFXVRKJ-ZDUSSCGKSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(2S)-2-[6-[(2,4-diaminopteridin-6-yl)methylamino]-3-oxo-1H-isoindol-2-yl]pentanedioic acid
Database Links
BindingDB Ligand 50158569
ChEMBL Ligand CHEMBL390990
GtoPdb PubChem SID 310264671
PubChem CID 11247965
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