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))
Compound class: Natural product
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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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
InChI Key HCZKYJDFEPMADG-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes (FDA (1992))
Withdrawn drug? Yes
IUPAC Name Click here for help
4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
International Nonproprietary Names Click here for help
INN number INN
6615 masoprocol
Synonyms Click here for help
Actinex®
Database Links Click here for help
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
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