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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:58:17 UTC

Update Date

2022-03-07 02:54:00 UTC

HMDB ID

HMDB0034178

Secondary Accession Numbers

HMDB34178

Metabolite Identification

Common Name

Guaiacin

Description

Guaiacin belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. Guaiacin has been detected, but not quantified in, herbs and spices and ucuhubas (Virola surinamensis). This could make guaiacin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Guaiacin.

Structure

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

HMDB0034178
     RDKit          3D
Guaiacin
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.4896    0.4484   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5374   -0.2673    0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893   -0.8201    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1744   -0.7011    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -1.2509    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783   -1.1125    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092    0.1378    0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.4335    1.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776    1.5613    2.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582    1.8217    3.6443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544    2.4114    1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    3.5605    1.6694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    4.4551    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    2.1222   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881    0.9920   -0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2882    0.7068   -1.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.8157   -2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -1.2433   -3.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2099   -1.3838   -1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1570   -2.8969   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -1.9469    2.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2641   -2.0934    2.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313   -1.5311    2.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6373   -1.6673    2.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4802    0.9041   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    1.2351   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661   -0.1972   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754   -0.1381   -0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9539   -1.9314    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489   -0.2121    2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489    2.6494    3.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1010    5.2364    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443    4.8340    0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667    3.8503    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231    2.7764   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074    1.1205   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.0603   -2.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3056   -1.1245   -1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110   -2.1181   -3.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8535   -0.3681   -4.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4574   -1.5108   -3.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735   -0.9708   -1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996   -3.3754   -0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8529   -3.2772   -1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4539   -3.1068   -2.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449   -2.3712    2.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952   -2.6429    3.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4548   -1.2422    2.4734 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 19  6  1  0
 15  7  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
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
M  END


  Mrv0541 05061307382D          

 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  1  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  2  0  0  0  0
 19  9  1  0  0  0  0
 19 17  2  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 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>
HMDB0034178

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/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/h5-6,8-12,20-22H,7H2,1-4H3

> <INCHI_KEY>
TZAAYUCUPIYQBR-UHFFFAOYSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.4022

> <EXACT_MASS>
328.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.379048696776806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.497888109

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.473043833368424

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.849501976916102

> <JCHEM_PKA_STRONGEST_BASIC>
-4.58852653166971

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
94.16919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034178
     RDKit          3D
Guaiacin
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.4896    0.4484   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5374   -0.2673    0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893   -0.8201    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1744   -0.7011    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -1.2509    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783   -1.1125    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092    0.1378    0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.4335    1.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776    1.5613    2.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582    1.8217    3.6443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544    2.4114    1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    3.5605    1.6694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    4.4551    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    2.1222   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881    0.9920   -0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2882    0.7068   -1.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.8157   -2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -1.2433   -3.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2099   -1.3838   -1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1570   -2.8969   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -1.9469    2.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2641   -2.0934    2.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313   -1.5311    2.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6373   -1.6673    2.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4802    0.9041   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    1.2351   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661   -0.1972   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754   -0.1381   -0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9539   -1.9314    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489   -0.2121    2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489    2.6494    3.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1010    5.2364    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443    4.8340    0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667    3.8503    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231    2.7764   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074    1.1205   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.0603   -2.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3056   -1.1245   -1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110   -2.1181   -3.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8535   -0.3681   -4.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4574   -1.5108   -3.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735   -0.9708   -1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996   -3.3754   -0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8529   -3.2772   -1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4539   -3.1068   -2.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449   -2.3712    2.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952   -2.6429    3.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4548   -1.2422    2.4734 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 19  6  1  0
 15  7  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
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  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    HMDB0034178
HETATM    1  C1  UNL     1       4.490   0.448  -0.720  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.537  -0.267   0.500  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.389  -0.820   1.004  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.174  -0.701   0.359  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.003  -1.251   0.850  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.278  -1.113   0.143  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.009   0.138   0.509  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.210   0.433   1.854  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.878   1.561   2.276  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.058   1.822   3.644  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.354   2.411   1.300  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.035   3.560   1.669  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.539   4.455   0.694  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.158   2.122  -0.033  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.488   0.992  -0.459  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.288   0.707  -1.908  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.425  -0.816  -2.014  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.466  -1.243  -3.465  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.210  -1.384  -1.316  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.157  -2.897  -1.531  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.069  -1.947   2.039  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.264  -2.093   2.723  1.00  0.00           C  
HETATM   23  C20 UNL     1       3.431  -1.531   2.211  1.00  0.00           C  
HETATM   24  O4  UNL     1       4.637  -1.667   2.882  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.480   0.904  -0.914  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.692   1.235  -0.695  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.266  -0.197  -1.584  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.175  -0.138  -0.586  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.954  -1.931   0.550  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.849  -0.212   2.651  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.549   2.649   3.954  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.101   5.236   1.214  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.744   4.834   0.044  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.267   3.850   0.086  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.523   2.776  -0.831  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.107   1.121  -2.526  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.302   1.060  -2.243  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.306  -1.125  -1.449  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.111  -2.118  -3.526  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.854  -0.368  -4.032  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.457  -1.511  -3.809  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.673  -0.971  -1.833  1.00  0.00           H  
HETATM   43  H19 UNL     1      -0.900  -3.375  -0.835  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.853  -3.277  -1.258  1.00  0.00           H  
HETATM   45  H21 UNL     1      -0.454  -3.107  -2.556  1.00  0.00           H  
HETATM   46  H22 UNL     1       0.145  -2.371   2.404  1.00  0.00           H  
HETATM   47  H23 UNL     1       2.295  -2.643   3.656  1.00  0.00           H  
HETATM   48  H24 UNL     1       5.455  -1.242   2.473  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   21   21
CONECT    6    7   19   29
CONECT    7    8    8   15
CONECT    8    9   30
CONECT    9   10   11   11
CONECT   10   31
CONECT   11   12   14
CONECT   12   13
CONECT   13   32   33   34
CONECT   14   15   15   35
CONECT   15   16
CONECT   16   17   36   37
CONECT   17   18   19   38
CONECT   18   39   40   41
CONECT   19   20   42
CONECT   20   43   44   45
CONECT   21   22   46
CONECT   22   23   23   47
CONECT   23   24
CONECT   24   48
END

HMDB0034178
     RDKit          3D
Guaiacin
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.4896    0.4484   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5374   -0.2673    0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893   -0.8201    1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1744   -0.7011    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -1.2509    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783   -1.1125    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092    0.1378    0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.4335    1.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776    1.5613    2.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582    1.8217    3.6443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544    2.4114    1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    3.5605    1.6694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    4.4551    0.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    2.1222   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881    0.9920   -0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2882    0.7068   -1.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.8157   -2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -1.2433   -3.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2099   -1.3838   -1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1570   -2.8969   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -1.9469    2.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2641   -2.0934    2.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313   -1.5311    2.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6373   -1.6673    2.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4802    0.9041   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    1.2351   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661   -0.1972   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754   -0.1381   -0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9539   -1.9314    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489   -0.2121    2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489    2.6494    3.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1010    5.2364    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443    4.8340    0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667    3.8503    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231    2.7764   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074    1.1205   -2.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025    1.0603   -2.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3056   -1.1245   -1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110   -2.1181   -3.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8535   -0.3681   -4.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4574   -1.5108   -3.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735   -0.9708   -1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996   -3.3754   -0.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8529   -3.2772   -1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4539   -3.1068   -2.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449   -2.3712    2.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952   -2.6429    3.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4548   -1.2422    2.4734 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 19  6  1  0
 15  7  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
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Guaiacin	HMDB
4,4'-Dihydroxy-3',5-dimethoxy-2,7'-cyclolignan	HMDB
5,6,7,8-tetrahydro-8-(4-Hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-2-naphthalenol, 9ci	HMDB

Chemical Formula

C₂₀H₂₄O₄

Average Molecular Weight

328.4022

Monoisotopic Molecular Weight

328.167459256

IUPAC Name

8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Traditional Name

8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

CAS Registry Number

36531-08-5

SMILES

COC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C20H24O4/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/h5-6,8-12,20-22H,7H2,1-4H3

InChI Key

TZAAYUCUPIYQBR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Methoxyphenol
Tetralin
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034178)

Cellular substructure

Membrane (HMDB: HMDB0034178)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034178)

Source

Exogenous

Food

Food (HMDB: HMDB0034178)

Herb and spice

Oilseed crop

Ucuhuba (FooDB: FOOD00777)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034178)

Not Available

Nutrient (HMDB: HMDB0034178)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	204 - 206 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.98 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	0.0093 g/L	ALOGPS
logP	4.08	ALOGPS
logP	4.5	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	-4.6	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	94.17 m³·mol⁻¹	ChemAxon
Polarizability	36.38 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]+	179.926	31661259
DarkChem	[M-H]-	177.81	31661259
DeepCCS	[M+H]+	186.541	30932474
DeepCCS	[M-H]-	184.183	30932474
DeepCCS	[M-2H]-	218.381	30932474
DeepCCS	[M+Na]+	193.668	30932474
AllCCS	[M+H]+	179.2	32859911
AllCCS	[M+H-H2O]+	176.0	32859911
AllCCS	[M+NH4]+	182.2	32859911
AllCCS	[M+Na]+	183.1	32859911
AllCCS	[M-H]-	186.0	32859911
AllCCS	[M+Na-2H]-	185.8	32859911
AllCCS	[M+HCOO]-	185.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Guaiacin	COC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C1	4348.2	Standard polar	33892256
Guaiacin	COC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C1	2708.0	Standard non polar	33892256
Guaiacin	COC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C1	2711.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Guaiacin,1TMS,isomer #1	COC1=CC(C2C3=CC(O[Si](C)(C)C)=C(OC)C=C3CC(C)C2C)=CC=C1O	2785.6	Semi standard non polar	33892256
Guaiacin,1TMS,isomer #2	COC1=CC2=C(C=C1O)C(C1=CC=C(O[Si](C)(C)C)C(OC)=C1)C(C)C(C)C2	2812.2	Semi standard non polar	33892256
Guaiacin,2TMS,isomer #1	COC1=CC(C2C3=CC(O[Si](C)(C)C)=C(OC)C=C3CC(C)C2C)=CC=C1O[Si](C)(C)C	2751.8	Semi standard non polar	33892256
Guaiacin,1TBDMS,isomer #1	COC1=CC(C2C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CC(C)C2C)=CC=C1O	3065.2	Semi standard non polar	33892256
Guaiacin,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)C(C)C(C)C2	3078.5	Semi standard non polar	33892256
Guaiacin,2TBDMS,isomer #1	COC1=CC(C2C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CC(C)C2C)=CC=C1O[Si](C)(C)C(C)(C)C	3225.2	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 - Guaiacin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0198000000-4fdda0c8dad227ff180b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guaiacin GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-0000900000-fcd558b5a50b01c07ed5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guaiacin 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 - Guaiacin 10V, Positive-QTOF	splash10-004i-0019000000-45d47c1564ec1f47ea2d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 20V, Positive-QTOF	splash10-004j-2296000000-51e284b28ea1bf2ab44c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 40V, Positive-QTOF	splash10-03di-4493000000-0c1a94551b40aeb2cef9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 10V, Negative-QTOF	splash10-004i-0009000000-573fa998ce549534ff77	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 20V, Negative-QTOF	splash10-004i-0029000000-95b54e3e9471b86d6655	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 40V, Negative-QTOF	splash10-06si-0091000000-56e43fae76d0839fab2d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 10V, Positive-QTOF	splash10-004i-0019000000-b7dca4be8a4ad70859e9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 20V, Positive-QTOF	splash10-004i-0359000000-77f1e52ea8faba694831	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 40V, Positive-QTOF	splash10-004l-0492000000-d66710f686ad08bb00b9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 10V, Negative-QTOF	splash10-004i-0009000000-fd417bc7f7b273e09154	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 20V, Negative-QTOF	splash10-01ta-0079000000-c103e8574373678ee641	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacin 40V, Negative-QTOF	splash10-0012-0192000000-7131ed9576e99082bb21	2021-09-25	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

FDB012470

KNApSAcK ID

C00037221

Chemspider ID

35013705

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14681584

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1840961

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 Guaiacin (HMDB0034178)

MOL for HMDB0034178 (Guaiacin)

3D MOL for HMDB0034178 (Guaiacin)

3D SDF for HMDB0034178 (Guaiacin)

3D-SDF for HMDB0034178 (Guaiacin)

PDB for HMDB0034178 (Guaiacin)

3D PDB for HMDB0034178 (Guaiacin)

SMILES for HMDB0034178 (Guaiacin)

INCHI for HMDB0034178 (Guaiacin)

Structure for HMDB0034178 (Guaiacin)

3D Structure for HMDB0034178 (Guaiacin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra