Marvin  05011316122D          

 22 23  0  0  0  0            999 V2000
   10.5472   -5.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5472   -6.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8046   -6.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1033   -6.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1033   -5.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8046   -5.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4020   -6.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6594   -6.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9581   -6.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2568   -6.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5555   -6.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5555   -7.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129   -8.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1117   -7.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1117   -6.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129   -6.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6594   -5.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9581   -7.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -8.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2485   -5.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2485   -6.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -6.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  1  2  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8 17  1  0  0  0  0
  2  3  1  0  0  0  0
  9 18  1  0  0  0  0
  8  9  1  0  0  0  0
 14 19  1  0  0  0  0
  3  4  2  0  0  0  0
  1 20  1  0  0  0  0
  9 10  1  0  0  0  0
  2 21  1  0  0  0  0
  4  5  1  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <ID>
CHEBI:7625

> <NAME>
nordihydroguaiaretic acid

> <DEFINITION>
A tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor.

> <STAR>
3

> <SYNONYM>
NSC 4291; norhydroguaiaretic acid; nordihydroguaiaretic acid (unspecified); nordihydroguaiaretic acid; NDGA; beta,gamma-dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butane; 4,4'-(2,3-dimethyltetramethylene)dipyrocatechol; 4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol); 2,3-bis(3,4-dihydroxyphenylmethyl)butane; 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane

> <IUPAC_NAME>
4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol

> <FORMULA>
C18H22O4

> <MASS>
302.36490

> <MONOISOTOPIC_MASS>
302.15181

> <CHARGE>
0

> <SMILES>
CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1

> <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

> <INCHIKEY>
HCZKYJDFEPMADG-UHFFFAOYSA-N

> <CAS_REGISTRY_NUMBER>
500-38-9

> <REAXYS_REGISTRY_NUMBER>
9803564

> <CHEMIDPLUS>
500-38-9

> <KEGG_COMPOUND_ACCESSION>
C10719

> <LINCS_ACCESSION>
LSM-6507

> <METACYC_ACCESSION>
CPD-7661

> <NIST_CHEMISTRY_WEBBOOK>
500-38-9

> <WIKIPEDIA_ACCESSION>
Nordihydroguaiaretic_acid

> <PUBMED_CITATION>
12375879; 14706572; 15389564; 15814253; 16061348; 18631321; 20848390; 21264886; 21858850; 22325100; 22432798; 23044922; 23053656; 23563831; 23603407; 25380600

$$$$