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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:32:47 UTC

Update Date

2022-03-07 02:54:54 UTC

HMDB ID

HMDB0036409

Secondary Accession Numbers

HMDB36409

Metabolite Identification

Common Name

1,2-Dihydrodehydroguaiaretic acid

Description

1,2-Dihydrodehydroguaiaretic acid belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. 1,2-Dihydrodehydroguaiaretic acid has been detected, but not quantified in, herbs and spices. This could make 1,2-dihydrodehydroguaiaretic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1,2-Dihydrodehydroguaiaretic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0036409
     RDKit          3D
1,2-Dihydrodehydroguaiaretic acid
 46 48  0  0  0  0  0  0  0  0999 V2000
   -4.9847    3.1761   -1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863    3.2521   -1.3916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    2.2124   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2540    0.9760   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968   -0.0246   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8803   -1.2892    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -2.3527    0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6948   -3.6808    0.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -2.1350    0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286   -3.2413    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1885   -0.8987    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822   -0.7246    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    0.2995    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3318    0.5538    0.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143    1.7950    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0178    2.7484    0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494   -0.4387   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190   -0.9098    0.9218 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001   -1.5607   -0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1053   -1.7355   -0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046    0.1617   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5605    1.3966   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097    2.4396   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8479    3.6584   -1.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4349    3.0546   -0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251    4.1411   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2414    2.3795   -2.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    0.7784   -0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662   -1.4395    0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8368   -3.8151    1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430   -3.8501    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0105   -4.5063    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083   -4.0236    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972   -2.9963    1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -3.7499    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2257    1.0374    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6538    0.6831    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309    3.6835    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128    2.9810    1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064    2.4217    1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    0.0658   -0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845   -1.5942    0.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -2.3551   -1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143   -2.5870   -0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    1.5814   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982    4.4316   -1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
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  4 28  1  0
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 16 40  1  0
 17 41  1  0
 18 42  1  0
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 20 44  1  0
 22 45  1  0
 24 46  1  0
M  END

  Mrv0541 05061309072D          

 24 26  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    2.8579    0.0000    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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
    3.5724   -1.2375    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    4.2868   -1.6500    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
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 11  1  1  0  0  0  0
 11  7  2  0  0  0  0
 12  2  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  7  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  2  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17 10  1  0  0  0  0
 18  8  1  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 19 17  2  0  0  0  0
 20 12  2  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
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 22 17  1  0  0  0  0
 23  3  1  0  0  0  0
 23 18  1  0  0  0  0
 24  4  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036409

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C=C(C=CC1O)C1=C(C)C(C)=CC2=CC(OC)=C(O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O4/c1-11-7-14-9-19(24-4)17(22)10-15(14)20(12(11)2)13-5-6-16(21)18(8-13)23-3/h5-10,16,18,21-22H,1-4H3

> <INCHI_KEY>
HKKHLGFWQTXGPF-UHFFFAOYSA-N

> <FORMULA>
C20H22O4

> <MOLECULAR_WEIGHT>
326.3863

> <EXACT_MASS>
326.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.33357731379886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-3-methoxy-6,7-dimethylnaphthalen-2-ol

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.5078694919999998

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.752039925626086

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.708517300698812

> <JCHEM_PKA_STRONGEST_BASIC>
-3.344675515415771

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
96.66709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-3-methoxy-6,7-dimethylnaphthalen-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036409
     RDKit          3D
1,2-Dihydrodehydroguaiaretic acid
 46 48  0  0  0  0  0  0  0  0999 V2000
   -4.9847    3.1761   -1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863    3.2521   -1.3916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    2.2124   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2540    0.9760   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968   -0.0246   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8803   -1.2892    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -2.3527    0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6948   -3.6808    0.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -2.1350    0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286   -3.2413    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1885   -0.8987    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822   -0.7246    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    0.2995    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3318    0.5538    0.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143    1.7950    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0178    2.7484    0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494   -0.4387   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190   -0.9098    0.9218 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001   -1.5607   -0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1053   -1.7355   -0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046    0.1617   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5605    1.3966   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097    2.4396   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8479    3.6584   -1.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4349    3.0546   -0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251    4.1411   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2414    2.3795   -2.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    0.7784   -0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662   -1.4395    0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8368   -3.8151    1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430   -3.8501    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0105   -4.5063    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083   -4.0236    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972   -2.9963    1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -3.7499    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2257    1.0374    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6538    0.6831    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309    3.6835    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128    2.9810    1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064    2.4217    1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    0.0658   -0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845   -1.5942    0.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -2.3551   -1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143   -2.5870   -0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    1.5814   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982    4.4316   -1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 21  5  1  0
 20 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 13 36  1  0
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 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
 24 46  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -7.700   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       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5    6   13                                                       
CONECT    6    5   16                                                       
CONECT    7   11   14                                                       
CONECT    8   13   18                                                       
CONECT    9   14   19                                                       
CONECT   10   15   17                                                       
CONECT   11    1    7   12                                                  
CONECT   12    2   11   20                                                  
CONECT   13    5    8   20                                                  
CONECT   14    7    9   15                                                  
CONECT   15   10   14   20                                                  
CONECT   16    6   18   21                                                  
CONECT   17   10   19   22                                                  
CONECT   18    8   16   23                                                  
CONECT   19    9   17   24                                                  
CONECT   20   12   13   15                                                  
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    3   18                                                       
CONECT   24    4   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0036409
HETATM    1  C1  UNL     1      -4.985   3.176  -1.470  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.586   3.252  -1.392  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.766   2.212  -0.999  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.254   0.976  -0.641  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.397  -0.025  -0.256  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.880  -1.289   0.057  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.104  -2.353   0.404  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.695  -3.681   0.723  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.733  -2.135   0.446  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.129  -3.241   0.852  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.189  -0.899   0.146  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.282  -0.725   0.143  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.893   0.299   0.675  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.332   0.554   0.710  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.514   1.795   0.055  1.00  0.00           O  
HETATM   16  C14 UNL     1       4.018   2.748   0.933  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.149  -0.439  -0.001  1.00  0.00           C  
HETATM   18  O3  UNL     1       5.119  -0.910   0.922  1.00  0.00           O  
HETATM   19  C16 UNL     1       3.400  -1.561  -0.575  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.105  -1.735  -0.537  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.005   0.162  -0.210  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.561   1.397  -0.576  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.410   2.440  -0.972  1.00  0.00           C  
HETATM   24  O4  UNL     1      -0.848   3.658  -1.321  1.00  0.00           O  
HETATM   25  H1  UNL     1      -5.435   3.055  -0.482  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.325   4.141  -1.944  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.241   2.379  -2.189  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.332   0.778  -0.658  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.966  -1.440   0.020  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.837  -3.815   1.821  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.643  -3.850   0.164  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.010  -4.506   0.414  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.108  -4.024   0.068  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.097  -2.996   1.274  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.426  -3.750   1.717  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.226   1.037   1.231  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.654   0.683   1.793  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.131   3.683   0.347  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.313   2.981   1.755  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.006   2.422   1.262  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.746   0.066  -0.818  1.00  0.00           H  
HETATM   42  H18 UNL     1       5.685  -1.594   0.521  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.991  -2.355  -1.103  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.614  -2.587  -0.998  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.512   1.581  -0.630  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.398   4.432  -1.609  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   28
CONECT    5    6    6   21
CONECT    6    7   29
CONECT    7    8    9    9
CONECT    8   30   31   32
CONECT    9   10   11
CONECT   10   33   34   35
CONECT   11   12   21   21
CONECT   12   13   13   20
CONECT   13   14   36
CONECT   14   15   17   37
CONECT   15   16
CONECT   16   38   39   40
CONECT   17   18   19   41
CONECT   18   42
CONECT   19   20   20   43
CONECT   20   44
CONECT   21   22
CONECT   22   23   23   45
CONECT   23   24
CONECT   24   46
END

HMDB0036409
     RDKit          3D
1,2-Dihydrodehydroguaiaretic acid
 46 48  0  0  0  0  0  0  0  0999 V2000
   -4.9847    3.1761   -1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863    3.2521   -1.3916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    2.2124   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2540    0.9760   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968   -0.0246   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8803   -1.2892    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -2.3527    0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6948   -3.6808    0.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -2.1350    0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286   -3.2413    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1885   -0.8987    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822   -0.7246    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    0.2995    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3318    0.5538    0.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143    1.7950    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0178    2.7484    0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494   -0.4387   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1190   -0.9098    0.9218 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001   -1.5607   -0.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1053   -1.7355   -0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046    0.1617   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5605    1.3966   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097    2.4396   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8479    3.6584   -1.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4349    3.0546   -0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3251    4.1411   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2414    2.3795   -2.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    0.7784   -0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662   -1.4395    0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8368   -3.8151    1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430   -3.8501    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0105   -4.5063    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083   -4.0236    0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972   -2.9963    1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -3.7499    1.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2257    1.0374    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6538    0.6831    1.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309    3.6835    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128    2.9810    1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064    2.4217    1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    0.0658   -0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845   -1.5942    0.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -2.3551   -1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143   -2.5870   -0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    1.5814   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982    4.4316   -1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 21  5  1  0
 20 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
 24 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dihydrodehydroguaiaretate	Generator
4,4'-Dihydroxy-3,3'-dimethoxy-2,7'-cyclolign-7-ene	HMDB
5'-Palmitoyl cytarabine	HMDB
Arabinosyl cytosine palmitate	HMDB
Aracytidine 5'-palmitate	HMDB
Myrisfragransin	HMDB
P-Ara-c	HMDB
Palm O-ara-c	HMDB
palmo-Ara-c	HMDB

Chemical Formula

C₂₀H₂₂O₄

Average Molecular Weight

326.3863

Monoisotopic Molecular Weight

326.151809192

IUPAC Name

8-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-3-methoxy-6,7-dimethylnaphthalen-2-ol

Traditional Name

8-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-3-methoxy-6,7-dimethylnaphthalen-2-ol

CAS Registry Number

135962-21-9

SMILES

COC1C=C(C=CC1O)C1=C(C)C(C)=CC2=CC(OC)=C(O)C=C12

InChI Identifier

InChI=1S/C20H22O4/c1-11-7-14-9-19(24-4)17(22)10-15(14)20(12(11)2)13-5-6-16(21)18(8-13)23-3/h5-10,16,18,21-22H,1-4H3

InChI Key

HKKHLGFWQTXGPF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

2-naphthol
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Secondary alcohol
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0036409)
Cell membrane (HMDB: HMDB0036409)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036409)

Source

Exogenous

Exogenous (HMDB: HMDB0036409)

Food

Food (HMDB: HMDB0036409)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0036409)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036409)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.84 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.5	ALOGPS
logP	3.51	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.71	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.67 m³·mol⁻¹	ChemAxon
Polarizability	36.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.014	31661259
DarkChem	[M-H]-	179.531	31661259
DeepCCS	[M-2H]-	214.522	30932474
DeepCCS	[M+Na]+	189.749	30932474
AllCCS	[M+H]+	180.1	32859911
AllCCS	[M+H-H2O]+	176.9	32859911
AllCCS	[M+NH4]+	183.2	32859911
AllCCS	[M+Na]+	184.0	32859911
AllCCS	[M-H]-	184.7	32859911
AllCCS	[M+Na-2H]-	184.4	32859911
AllCCS	[M+HCOO]-	184.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dihydrodehydroguaiaretic acid	COC1C=C(C=CC1O)C1=C(C)C(C)=CC2=CC(OC)=C(O)C=C12	4830.7	Standard polar	33892256
1,2-Dihydrodehydroguaiaretic acid	COC1C=C(C=CC1O)C1=C(C)C(C)=CC2=CC(OC)=C(O)C=C12	2703.8	Standard non polar	33892256
1,2-Dihydrodehydroguaiaretic acid	COC1C=C(C=CC1O)C1=C(C)C(C)=CC2=CC(OC)=C(O)C=C12	2960.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dihydrodehydroguaiaretic acid,1TMS,isomer #1	COC1=CC2=CC(C)=C(C)C(C3=CC(OC)C(O[Si](C)(C)C)C=C3)=C2C=C1O	2878.6	Semi standard non polar	33892256
1,2-Dihydrodehydroguaiaretic acid,1TMS,isomer #2	COC1=CC2=CC(C)=C(C)C(C3=CC(OC)C(O)C=C3)=C2C=C1O[Si](C)(C)C	2915.1	Semi standard non polar	33892256
1,2-Dihydrodehydroguaiaretic acid,2TMS,isomer #1	COC1=CC2=CC(C)=C(C)C(C3=CC(OC)C(O[Si](C)(C)C)C=C3)=C2C=C1O[Si](C)(C)C	2830.6	Semi standard non polar	33892256
1,2-Dihydrodehydroguaiaretic acid,1TBDMS,isomer #1	COC1=CC2=CC(C)=C(C)C(C3=CC(OC)C(O[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1O	3105.4	Semi standard non polar	33892256
1,2-Dihydrodehydroguaiaretic acid,1TBDMS,isomer #2	COC1=CC2=CC(C)=C(C)C(C3=CC(OC)C(O)C=C3)=C2C=C1O[Si](C)(C)C(C)(C)C	3152.8	Semi standard non polar	33892256
1,2-Dihydrodehydroguaiaretic acid,2TBDMS,isomer #1	COC1=CC2=CC(C)=C(C)C(C3=CC(OC)C(O[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1O[Si](C)(C)C(C)(C)C	3302.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1091000000-3d03905596bfa258617e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-7009700000-e5f4c07c96e50c488b07	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 10V, Positive-QTOF	splash10-004i-0029000000-34fc3c72dc65bc6523ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 20V, Positive-QTOF	splash10-004i-0196000000-53bfbe55fbe96b3d4e1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 40V, Positive-QTOF	splash10-056s-2290000000-254c27ee07ed7907748f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 10V, Negative-QTOF	splash10-004i-0009000000-c62749a65e58b2c02a3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 20V, Negative-QTOF	splash10-004i-0039000000-f92830628bd86f397632	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 40V, Negative-QTOF	splash10-05r0-1091000000-7a204103d3884b57a752	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 10V, Negative-QTOF	splash10-004i-0009000000-976dd6ecdf84064dc4ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 20V, Negative-QTOF	splash10-056r-0069000000-7fe2f601f4304010dcc8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 40V, Negative-QTOF	splash10-000i-0090000000-d37a3ac5ab6741b3b81e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 10V, Positive-QTOF	splash10-004i-0039000000-f59ad49a29f6ced3bdbe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 20V, Positive-QTOF	splash10-002b-0092000000-914040a9139f4dc55333	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydrodehydroguaiaretic acid 40V, Positive-QTOF	splash10-0ug0-3091000000-e412fbe184eb75cdfffe	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015289

KNApSAcK ID

C00054735

Chemspider ID

35014141

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751985

PDB ID

Not Available

ChEBI ID

175172

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855011

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1,2-Dihydrodehydroguaiaretic acid (HMDB0036409)

MOL for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

3D MOL for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

3D SDF for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

3D-SDF for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

PDB for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

3D PDB for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

SMILES for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

INCHI for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

Structure for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

3D Structure for HMDB0036409 (1,2-Dihydrodehydroguaiaretic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra