nordihydroguiaretic acid   Click here for help

GtoPdb Ligand ID: 4265

Abbreviated name: NDGA
Synonyms: Actinex®
Approved drug
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.
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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1992))
Withdrawn drug? Yes
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
6615 masoprocol
Synonyms Click here for help
Database Links Click here for help
CAS Registry No. 500-38-9 (source: Scifinder)
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
UniChem Compound Search for chemical match using the InChIKey HCZKYJDFEPMADG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HCZKYJDFEPMADG-UHFFFAOYSA-N
Wikipedia Nordihydroguaiaretic_acid, Masoprocol