NORDIHYDROGUAIARETIC ACID
Relevant Data
Food Additives Approved in the United States
General Information
| Synonyms: | NDGA |
| Chemical Names: | NORDIHYDROGUAIARETIC ACID; beta,gamma-DIMETHYL-alpha,delta-bis(3,4-DIHYDROPHENYL)BUTANE; 4,4'-(2,3-DIMETHYLTETRAMETHYLENE)-DIPYROCATECHOL |
| CAS number: | 500-38-9 |
| Functional Class: |
Food Additives ANTIOXIDANT |
From apps.who.int
Evaluations
| Evaluation year: | 1973 |
| ADI: | NO ADI ALLOCATED |
| Meeting: | 17 |
| Specs Code: | R |
| Report: | NMRS 53/TRS 539-JECFA 17/36 |
| Tox Monograph: | FAS 5/NMRS 53A-JECFA 17/197 |
| Specification: | COMPENDIUM ADDENDUM 12/FNP 52 Add. 12/67 (METALS LIMITS) (2004). R; FAO JECFA Monographs 1 vol.2/451 |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 4534 |
| IUPAC Name | 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol |
| 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 |
| Canonical SMILES | CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O |
| Molecular Formula | C18H22O4 |
| Wikipedia | nordihydroguaiaretic acid |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 302.37 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 303.0 |
| CACTVS Substructure Key Fingerprint | A A A D c e B 4 O A A A A A A A A A A A A A A A A A A A A A A A A A A w Y A A A A A A A A A A B Q A A A G g A A C A A A D Q S A m A A y B o A A A g C A A i B C A A A C A A A g I A A I i A A G i I g J J i K C E R K A c A E k w B E J m A e A w P A O o A A B A A A A Q A B A A A I A A A C A A A A A A A A A A A = = |
| Topological Polar Surface Area | 80.9 |
| Monoisotopic Mass | 302.152 |
| Exact Mass | 302.152 |
| XLogP3 | None |
| XLogP3-AA | 4.3 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.5361 |
| Human Intestinal Absorption | HIA+ | 0.9350 |
| Caco-2 Permeability | Caco2+ | 0.6215 |
| P-glycoprotein Substrate | Substrate | 0.6654 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9519 |
| Non-inhibitor | 0.9144 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8860 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8535 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7194 |
| CYP450 2D6 Substrate | Non-substrate | 0.8261 |
| CYP450 3A4 Substrate | Non-substrate | 0.5171 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9107 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8891 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8262 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8628 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5833 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5322 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9462 |
| Non-inhibitor | 0.6288 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.8614 |
| Fish Toxicity | High FHMT | 0.9966 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9638 |
| Honey Bee Toxicity | High HBT | 0.6227 |
| Biodegradation | Not ready biodegradable | 0.9632 |
| Acute Oral Toxicity | III | 0.8109 |
| Carcinogenicity (Three-class) | Non-required | 0.6290 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4555 | LogS |
| Caco-2 Permeability | 0.5937 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1491 | LD50, mol/kg |
| Fish Toxicity | 0.0370 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.1163 | pIGC50, ug/L |
From admetSAR
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lignans, neolignans and related compounds |
| Class | Dibenzylbutane lignans |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dibenzylbutane lignans |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Dibenzylbutane lignan skeleton - Phenylpropane - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. |
From ClassyFire