NP-MRD: Showing NP-Card for nordihydroguaiaretic acid (NP0212079)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 10:37:22 UTC

Updated at

2022-09-05 10:37:22 UTC

NP-MRD ID

NP0212079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nordihydroguaiaretic acid

Description

nordihydroguaiaretic acid is found in Larrea cuneifolia, Larrea divaricata and Schisandra chinensis. nordihydroguaiaretic acid was first documented in 2001 (PMID: 12375879).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.0859    0.1251    0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2490   -0.5205   -0.8091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6577   -1.0488   -0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.0452   -0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0320    0.7000   -1.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160    1.6820   -1.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6875    1.9186   -0.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6779    2.9128   -0.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3900    1.1895    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0659    1.4287    1.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3970    0.2026    0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6743   -1.6845   -1.0479 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4255   -2.7288    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0933   -1.3737   -1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -0.6403   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488   -1.3352    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.7375    1.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2759    0.6332    1.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857    1.2539    2.8030 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    1.3637    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7749    2.7371    0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9586    0.7327   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9964    0.0594    1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.3499    1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885    1.1973    0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0911    0.2570   -1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456   -1.8021   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513   -1.6796   -1.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5483    0.5717   -2.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2525    2.2582   -2.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8960    3.4449   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8922    0.9281    2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2442   -0.3318    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3100   -2.1995   -2.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3513   -2.3401    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548   -3.3550   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3458   -3.3873    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -2.3681   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -0.8328   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3874   -2.4152    0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198   -1.3209    2.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0827    2.2317    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313    3.3375    1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4960    1.3311   -0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 11  2  0
 11  9  1  0
  9 10  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  2  0
  2 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 22  2  0
 22 20  1  0
 20 21  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
  5  4  1  0
 16 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  3 28  1  0
 11 33  1  0
 10 32  1  0
  8 31  1  0
  6 30  1  0
  5 29  1  0
 12 34  1  6
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 22 44  1  0
 21 43  1  0
 19 42  1  0
 17 41  1  0
 16 40  1  0
M  END


  Mrv1652305221920182D          

 22 23  0  0  0  0            999 V2000
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 17 15  2  0  0  0  0
 18 10  1  0  0  0  0
 18 16  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC1=CC(O)=C(O)C=C1)C(C)CC1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C18H22O4

> <MOLECULAR_WEIGHT>
302.3649

> <EXACT_MASS>
302.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.838177847502095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
4.758522743999999

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.808299093340917

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.206546692580925

> <JCHEM_PKA_STRONGEST_BASIC>
-6.25042985340511

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
86.61899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nordihydroguaiaretic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    5   13                                                       
CONECT    4    6   14                                                       
CONECT    5    3   15                                                       
CONECT    6    4   16                                                       
CONECT    7   11   13                                                       
CONECT    8   12   14                                                       
CONECT    9   13   17                                                       
CONECT   10   14   18                                                       
CONECT   11    1    7   12                                                  
CONECT   12    2    8   11                                                  
CONECT   13    3    7    9                                                  
CONECT   14    4    8   10                                                  
CONECT   15    5   17   19                                                  
CONECT   16    6   18   20                                                  
CONECT   17    9   15   21                                                  
CONECT   18   10   16   22                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane	ChEBI
2,3-Bis(3,4-dihydroxyphenylmethyl)butane	ChEBI
4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)	ChEBI
4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol	ChEBI
beta,gamma-Dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butane	ChEBI
NDGA	ChEBI
Norhydroguaiaretic acid	ChEBI
NSC 4291	ChEBI
b,g-Dimethyl-a,delta-bis(3,4-dihydroxyphenyl)butane	Generator
Β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butane	Generator
Norhydroguaiaretate	Generator
b,g-Dimethyl-a,δ-bis(3,4-dihydroxyphenyl)butane	Generator
(R,s)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatechol	MeSH

Chemical Formula

C₁₈H₂₂O₄

Average Mass

302.3649 Da

Monoisotopic Mass

302.15181 Da

IUPAC Name

4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol

Traditional Name

nordihydroguaiaretic acid

CAS Registry Number

Not Available

SMILES

CC(CC1=CC(O)=C(O)C=C1)C(C)CC1=CC(O)=C(O)C=C1

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Larrea cuneifolia	LOTUS Database	35616633
Larrea divaricata	LOTUS Database	35616633
Schisandra chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:7625 )
tetrol (CHEBI:7625 )
lignan (CHEBI:7625 )
a small molecule (CPD-7661 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.44	ALOGPS
logP	4.76	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.62 m³·mol⁻¹	ChemAxon
Polarizability	32.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011903

KNApSAcK ID

C00000693

Chemspider ID

Not Available

KEGG Compound ID

C10719

BioCyc ID

CPD-7661

BiGG ID

Not Available

Wikipedia Link

Nordihydroguaiaretic_acid

METLIN ID

Not Available

PubChem Compound

4534

PDB ID

Not Available

ChEBI ID

7625

Good Scents ID

Not Available

References

General References

McDonald RW, Bunjobpon W, Liu T, Fessler S, Pardo OE, Freer IK, Glaser M, Seckl MJ, Robins DJ: Synthesis and anticancer activity of nordihydroguaiaretic acid (NDGA) and analogues. Anticancer Drug Des. 2001 Dec;16(6):261-70. [PubMed:12375879 ]
Fujimoto N, Kohta R, Kitamura S: Estrogenic activity of an antioxidant, nordihydroguaiaretic acid (NDGA). Life Sci. 2004 Jan 30;74(11):1417-25. doi: 10.1016/j.lfs.2003.08.012. [PubMed:14706572 ]
Ito H, Ueda H, Iwamoto I, Inaguma Y, Takizawa T, Asano T, Kato K: Nordihydroguaiaretic acid (NDGA) blocks the differentiation of C2C12 myoblast cells. J Cell Physiol. 2005 Mar;202(3):874-9. doi: 10.1002/jcp.20177. [PubMed:15389564 ]
Arteaga S, Andrade-Cetto A, Cardenas R: Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid. J Ethnopharmacol. 2005 Apr 26;98(3):231-9. doi: 10.1016/j.jep.2005.02.002. [PubMed:15814253 ]
Siddique YH, Beg T, Afzal M: Protective effect of nordihydroguaiaretic acid (NDGA) against norgestrel induced genotoxic damage. Toxicol In Vitro. 2006 Mar;20(2):227-33. doi: 10.1016/j.tiv.2005.06.027. Epub 2005 Aug 2. [PubMed:16061348 ]
LOTUS database [Link]

Showing NP-Card for nordihydroguaiaretic acid (NP0212079)

MOL for NP0212079 (nordihydroguaiaretic acid)

3D MOL for NP0212079 (nordihydroguaiaretic acid)

3D SDF for NP0212079 (nordihydroguaiaretic acid)

3D-SDF for NP0212079 (nordihydroguaiaretic acid)

PDB for NP0212079 (nordihydroguaiaretic acid)

3D PDB for NP0212079 (nordihydroguaiaretic acid)

SMILES for NP0212079 (nordihydroguaiaretic acid)

INCHI for NP0212079 (nordihydroguaiaretic acid)

Structure for NP0212079 (nordihydroguaiaretic acid)

3D Structure for NP0212079 (nordihydroguaiaretic acid)