nordihydroguiaretic acid   

GtoPdb Ligand ID: 4265

Abbreviated name: NDGA
Synonyms: Actinex®
nordihydroguiaretic acid is an approved drug (FDA (1992))
Comment: Although we show the non-isomeric molecule, the approved drug masoprocol is a specific stereoisomer of NGDA, with IUPAC name 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol (as shown in the PubChem record). The ChEMBL record displays the non-stereoisomeric molecule. PubChem lists 6 stereoisomers of this compound.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 0
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 80.92
Molecular weight 302.15
XLogP 5.49
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(C(Cc1ccc(c(c1)O)O)C)Cc1ccc(c(c1)O)O
Isomeric SMILES CC(C(Cc1ccc(c(c1)O)O)C)Cc1ccc(c(c1)O)O
InChI InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3
InChI Key HCZKYJDFEPMADG-UHFFFAOYSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (FDA (1992))
Withdrawn drug? Yes
IUPAC Name
4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
International Nonproprietary Names
INN number INN
6615 masoprocol
Synonyms
Actinex®
Database Links
CAS Registry No. 500-38-9 (source: Scifinder)
ChEMBL Ligand CHEMBL52
DrugBank Ligand DB00179
GtoPdb PubChem SID 178101082
PubChem CID 4534
Search Google for chemical match using the InChIKey HCZKYJDFEPMADG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HCZKYJDFEPMADG
Search PubMed clinical trials masoprocol
Search PubMed titles masoprocol
Search PubMed titles/abstracts masoprocol
Search UniChem for chemical match using the InChIKey HCZKYJDFEPMADG-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone HCZKYJDFEPMADG
Wikipedia Nordihydroguaiaretic_acid, Masoprocol