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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-23 10:11:27 UTC

Update Date

2021-09-14 15:43:43 UTC

HMDB ID

HMDB0005056

Secondary Accession Numbers

HMDB05056

Metabolite Identification

Common Name

Enterodiol

Description

Enterodiol is one of the most important lignan-type phytoestrogens identified in serum, urine, bile, and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have been categorized according to their chemical structures as isoflavones, lignans, and coumestans. Enterodiol is formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole-grain cereals (barley, rye, and wheat), seeds, nuts, legumes, and vegetables (PMID: 12270221 , J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309.). Enterodiol is a biomarker for the consumption of soy beans and other soy products.

Structure

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

HMDB0005056
     RDKit          3D
Enterodiol
 44 45  0  0  0  0  0  0  0  0999 V2000
   -1.3693   -2.2865   -1.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -1.9549   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -0.6571    0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3910    0.4515   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8407    0.6270   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7943   -0.0148   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522    0.1277   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5598    0.9575    0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6329    1.6217    0.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585    2.4488    1.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2944    1.4502    0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7075   -0.7906   -0.0070 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2282   -1.8700    0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9818   -1.6116    2.2490 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941    0.5168    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681    0.4295    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381    0.1676    1.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101    0.0682    1.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6676    0.2327   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305    0.4967   -1.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6218    0.6587   -2.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5349    0.5942   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -1.6653   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.7855    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829   -2.8008    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086   -0.4696    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    1.4477   -0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038    0.3133   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191   -0.6664   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8864   -0.3886   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174    1.0846    0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537    3.4340    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700    1.9574    1.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.1798   -1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8220   -2.8729    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3386   -1.9508    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -0.6708    2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207    1.1882   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1134    0.9228    1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    0.0223    2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6018   -0.1387    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7690    0.1587   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9328    1.5978   -2.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665    0.7990   -2.0551 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  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 11  5  1  0
 22 16  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  1
  4 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  6
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
M  END


  Mrv1652306071918382D          

 22 23  0  0  0  0            999 V2000
 9999.4361 9999.3051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.7221 9998.8921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.0075 9999.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1494 9999.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7221 9998.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0075 9997.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.1519 9998.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0088 9998.8921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.436110000.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.151910000.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.580010000.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.865710000.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8657 9999.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5800 9998.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2944 9999.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.294410000.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2929 9998.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5785 9999.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8640 9998.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8639 9998.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5784 9997.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2929 9998.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1  9  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  6  0  0  0
  5  6  1  0  0  0  0
  9 10  1  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
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
  3 17  1  0  0  0  0
 19  4  1  0  0  0  0
  7 13  1  0  0  0  0
 15  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005056

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1

> <INCHI_KEY>
DWONJCNDULPHLV-HOTGVXAUSA-N

> <FORMULA>
C18H22O4

> <MOLECULAR_WEIGHT>
302.3649

> <EXACT_MASS>
302.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.76260824205408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.648203614

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.395474277447398

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.793418141582793

> <JCHEM_PKA_STRONGEST_BASIC>
-2.603209181436301

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
86.36060000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-enterodiol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005056
     RDKit          3D
Enterodiol
 44 45  0  0  0  0  0  0  0  0999 V2000
   -1.3693   -2.2865   -1.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -1.9549   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -0.6571    0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3910    0.4515   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8407    0.6270   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7943   -0.0148   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522    0.1277   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5598    0.9575    0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6329    1.6217    0.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585    2.4488    1.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2944    1.4502    0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7075   -0.7906   -0.0070 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2282   -1.8700    0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9818   -1.6116    2.2490 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941    0.5168    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681    0.4295    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381    0.1676    1.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101    0.0682    1.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6676    0.2327   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305    0.4967   -1.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6218    0.6587   -2.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5349    0.5942   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -1.6653   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.7855    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829   -2.8008    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086   -0.4696    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    1.4477   -0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038    0.3133   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191   -0.6664   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8864   -0.3886   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174    1.0846    0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537    3.4340    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700    1.9574    1.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.1798   -1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8220   -2.8729    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3386   -1.9508    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -0.6708    2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207    1.1882   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1134    0.9228    1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    0.0223    2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6018   -0.1387    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7690    0.1587   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9328    1.5978   -2.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665    0.7990   -2.0551 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  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 11  5  1  0
 22 16  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  1
  4 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  6
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 07-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUN-19         0                                  
HETATM    1  C   UNK     0    8665.6148665.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.2818664.599   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.9478665.370   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8657.6128665.370   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8664.2818663.059   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8662.9478662.290   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.9508664.599   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8672.2838664.599   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8665.6148666.910   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8666.9508667.680   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8669.6168667.680   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.2838666.910   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.2838665.370   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8669.6168664.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.9508665.370   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.9508666.910   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8661.6138664.599   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.2808665.369   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.9468664.599   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8658.9468663.059   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8660.2808662.289   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8661.6138663.059   0.000  0.00  0.00           C+0
CONECT    1    2    7    9                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2   17                                                       
CONECT    4   19                                                            
CONECT    5    2    6                                                       
CONECT    6    5                                                            
CONECT    7    1   13                                                       
CONECT    8   15                                                            
CONECT    9    1   10                                                       
CONECT   10    9                                                            
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14    7                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16    8                                                  
CONECT   16   15   11                                                       
CONECT   17   18   22    3                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20    4                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0005056
HETATM    1  O1  UNL     1      -1.369  -2.286  -1.494  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.486  -1.955  -0.166  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.785  -0.657   0.170  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.391   0.452  -0.637  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.841   0.627  -0.369  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.794  -0.015  -1.117  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.152   0.128  -0.887  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.560   0.958   0.145  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.633   1.622   0.921  1.00  0.00           C  
HETATM   10  O2  UNL     1      -5.058   2.449   1.952  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.294   1.450   0.657  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.708  -0.791  -0.007  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.228  -1.870   0.908  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.982  -1.612   2.249  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.394   0.517   0.176  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.868   0.430   0.020  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.638   0.168   1.129  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.010   0.068   1.083  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.668   0.233  -0.106  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.931   0.497  -1.240  1.00  0.00           C  
HETATM   21  O4  UNL     1       5.622   0.659  -2.431  1.00  0.00           O  
HETATM   22  C18 UNL     1       3.535   0.594  -1.174  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.858  -1.665  -2.037  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.567  -1.786   0.039  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.183  -2.801   0.483  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.009  -0.470   1.257  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.935   1.448  -0.393  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.204   0.313  -1.721  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.519  -0.666  -1.930  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.886  -0.389  -1.490  1.00  0.00           H  
HETATM   31  H9  UNL     1      -6.617   1.085   0.344  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.254   3.434   1.844  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.570   1.957   1.249  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.855  -1.180  -1.052  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.822  -2.873   0.680  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.339  -1.951   0.817  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.773  -0.671   2.443  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.021   1.188  -0.658  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.113   0.923   1.169  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.189   0.022   2.123  1.00  0.00           H  
HETATM   41  H19 UNL     1       5.602  -0.139   1.966  1.00  0.00           H  
HETATM   42  H20 UNL     1       6.769   0.159  -0.174  1.00  0.00           H  
HETATM   43  H21 UNL     1       5.933   1.598  -2.686  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.967   0.799  -2.055  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3   24   25
CONECT    3    4   12   26
CONECT    4    5   27   28
CONECT    5    6    6   11
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9   31
CONECT    9   10   11   11
CONECT   10   32
CONECT   11   33
CONECT   12   13   15   34
CONECT   13   14   35   36
CONECT   14   37
CONECT   15   16   38   39
CONECT   16   17   17   22
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20   42
CONECT   20   21   22   22
CONECT   21   43
CONECT   22   44
END

HMDB0005056
     RDKit          3D
Enterodiol
 44 45  0  0  0  0  0  0  0  0999 V2000
   -1.3693   -2.2865   -1.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -1.9549   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7848   -0.6571    0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3910    0.4515   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8407    0.6270   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7943   -0.0148   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522    0.1277   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5598    0.9575    0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6329    1.6217    0.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585    2.4488    1.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2944    1.4502    0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7075   -0.7906   -0.0070 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2282   -1.8700    0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9818   -1.6116    2.2490 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941    0.5168    0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681    0.4295    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381    0.1676    1.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0101    0.0682    1.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6676    0.2327   -0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305    0.4967   -1.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6218    0.6587   -2.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5349    0.5942   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -1.6653   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.7855    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1829   -2.8008    0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086   -0.4696    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    1.4477   -0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038    0.3133   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191   -0.6664   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8864   -0.3886   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174    1.0846    0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2537    3.4340    1.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700    1.9574    1.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.1798   -1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8220   -2.8729    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3386   -1.9508    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -0.6708    2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207    1.1882   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1134    0.9228    1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    0.0223    2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6018   -0.1387    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7690    0.1587   -0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9328    1.5978   -2.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665    0.7990   -2.0551 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  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 11  5  1  0
 22 16  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  1
  4 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  6
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Enterodiol	HMDB
(2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol	HMDB
Arbo 9	HMDB
[R-(R,r)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediol	HMDB
2,3-Bis(3'-hydroxybenzyl)butane-1,4-diol	HMDB
2,3-BHBBD	HMDB
2,3-Bis(3-hydroxybenzyl)butane-1,4-diol	HMDB
Enterodiol	HMDB

Chemical Formula

C₁₈H₂₂O₄

Average Molecular Weight

302.3649

Monoisotopic Molecular Weight

302.151809192

IUPAC Name

(2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

Traditional Name

(-)-enterodiol

CAS Registry Number

80226-00-2

SMILES

OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1

InChI Key

DWONJCNDULPHLV-HOTGVXAUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Dibenzylbutanediol lignans

Direct Parent

Dibenzylbutanediol lignans

Alternative Parents

Substituents

Dibenzylbutanediol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

lignan (CHEBI:81556 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17449591)

Excreta

Biofluid or Excreta

Urine (PMID: 17976571)
Feces (PMID: 27543620)

Cellular substructure

Membrane (HMDB: HMDB0005056)

Source

Endogenous

Endogenous (HMDB: HMDB0005056)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0005056)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0005056)

Tea

Tea products (HMDB: HMDB0005056)

Fat and oil

Olive oil (HMDB: HMDB0005056)

Fruit

Fruits (HMDB: HMDB0005056)

Vegetable

Vegetables (HMDB: HMDB0005056)

Legumes (HMDB: HMDB0005056)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0005056)

Nut

Nuts (HMDB: HMDB0005056)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0005056)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Fruits Consumption (MarkerDB: MDB00000467)
Vegetables Consumption (MarkerDB: MDB00000467)
Peach Consumption (MarkerDB: MDB00000467)
Berries Consumption (MarkerDB: MDB00000467)
Fruit Juices Consumption (MarkerDB: MDB00000467)
Soy Foods Consumption (MarkerDB: MDB00000467)
Fats Consumption (MarkerDB: MDB00000467)
Dark Bread Consumption (MarkerDB: MDB00000467)
Cereals Consumption (MarkerDB: MDB00000467)
Potato Consumption (MarkerDB: MDB00000467)
Chocolate Consumption (MarkerDB: MDB00000467)
Dietary Fibre Consumption (MarkerDB: MDB00000467)
Enterodiol Exposure (MarkerDB: MDB00000467)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	1.91	ALOGPS
logP	2.65	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-2.6	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	7	ChemAxon
Refractivity	86.36 m³·mol⁻¹	ChemAxon
Polarizability	32.76 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.001	31661259
DarkChem	[M-H]-	168.748	31661259
DeepCCS	[M+H]+	167.875	30932474
DeepCCS	[M-H]-	165.517	30932474
DeepCCS	[M-2H]-	199.537	30932474
DeepCCS	[M+Na]+	174.765	30932474
AllCCS	[M+H]+	173.4	32859911
AllCCS	[M+H-H2O]+	169.8	32859911
AllCCS	[M+NH4]+	176.6	32859911
AllCCS	[M+Na]+	177.6	32859911
AllCCS	[M-H]-	175.8	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.28 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0825 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1589.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	155.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	483.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	379.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	151.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	860.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	428.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1120.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	317.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	269.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	192.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	67.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Enterodiol	OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1	4406.2	Standard polar	33892256
Enterodiol	OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1	3058.2	Standard non polar	33892256
Enterodiol	OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1	3066.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Enterodiol,1TMS,isomer #1	C[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC1=CC=CC(O)=C1	2936.4	Semi standard non polar	33892256
Enterodiol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C[C@@H](CO)[C@H](CO)CC2=CC=CC(O)=C2)=C1	2862.8	Semi standard non polar	33892256
Enterodiol,2TMS,isomer #1	C[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)[C@H](CO)CC1=CC=CC(O)=C1	2813.9	Semi standard non polar	33892256
Enterodiol,2TMS,isomer #2	C[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO[Si](C)(C)C)CC1=CC=CC(O)=C1	2929.4	Semi standard non polar	33892256
Enterodiol,2TMS,isomer #3	C[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC1=CC=CC(O[Si](C)(C)C)=C1	2822.9	Semi standard non polar	33892256
Enterodiol,2TMS,isomer #4	C[Si](C)(C)OC1=CC=CC(C[C@@H](CO)[C@H](CO)CC2=CC=CC(O[Si](C)(C)C)=C2)=C1	2796.0	Semi standard non polar	33892256
Enterodiol,3TMS,isomer #1	C[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO[Si](C)(C)C)CC1=CC=CC(O[Si](C)(C)C)=C1	2808.3	Semi standard non polar	33892256
Enterodiol,3TMS,isomer #2	C[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)[C@H](CO)CC1=CC=CC(O[Si](C)(C)C)=C1	2770.6	Semi standard non polar	33892256
Enterodiol,4TMS,isomer #1	C[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)[C@H](CO[Si](C)(C)C)CC1=CC=CC(O[Si](C)(C)C)=C1	2781.4	Semi standard non polar	33892256
Enterodiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC1=CC=CC(O)=C1	3181.2	Semi standard non polar	33892256
Enterodiol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H](CO)[C@H](CO)CC2=CC=CC(O)=C2)=C1	3110.4	Semi standard non polar	33892256
Enterodiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@H](CO)CC1=CC=CC(O)=C1	3286.6	Semi standard non polar	33892256
Enterodiol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO[Si](C)(C)C(C)(C)C)CC1=CC=CC(O)=C1	3411.6	Semi standard non polar	33892256
Enterodiol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	3290.2	Semi standard non polar	33892256
Enterodiol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H](CO)[C@H](CO)CC2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)=C1	3284.2	Semi standard non polar	33892256
Enterodiol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO[Si](C)(C)C(C)(C)C)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	3445.6	Semi standard non polar	33892256
Enterodiol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@H](CO)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	3444.8	Semi standard non polar	33892256
Enterodiol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@H](CO[Si](C)(C)C(C)(C)C)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	3625.2	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 - Enterodiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2950000000-4ed8a5eb8bfaabb7a263	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enterodiol GC-MS (4 TMS) - 70eV, Positive	splash10-004i-6520390000-6840ee48e5d508b92d94	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enterodiol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 30V, Positive-QTOF	splash10-0a4i-0900000000-6fd5b1caf0b11ab3dd17	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOF	splash10-014i-0290000000-b01fb4b064e58a38e170	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 50V, Positive-QTOF	splash10-0a4i-3900000000-4ed09c20e4a4fb3f3875	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOF	splash10-0aor-0940000000-786ff272cb009339906f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOF	splash10-0aor-0940000000-a340102680583cfc68f0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 50V, Positive-QTOF	splash10-0pb9-3900000000-aa3626a0e9a6776858b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOF	splash10-0aor-0940000000-41e4cc9deb7aa9c799c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOF	splash10-014i-0290000000-179116fcc815df1446fe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 6V, Positive-QTOF	splash10-014i-0290000000-fd222de6f034fee01c31	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 50V, Positive-QTOF	splash10-0ar3-2900000000-ee35613960c900d06fb4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 6V, Positive-QTOF	splash10-014i-0290000000-2de3385ce84eba140c88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 30V, Positive-QTOF	splash10-0a4i-0900000000-9fba8f3772864b12ddbb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOF	splash10-014i-0290000000-ebad5296a50b0dcf053a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOF	splash10-0udr-0398000000-f09da6eee4bc76ff516a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 20V, Positive-QTOF	splash10-0frj-0971000000-bce5b39682ed3570612f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 40V, Positive-QTOF	splash10-05r9-0960000000-6920c1866fa29475fabc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 10V, Negative-QTOF	splash10-0udi-0039000000-c4358f7b97aab38a1ecf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 20V, Negative-QTOF	splash10-0udi-0096000000-fbf3e7cc759ef05d5425	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 40V, Negative-QTOF	splash10-0fdo-1690000000-046c3b836806f630a4ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 10V, Positive-QTOF	splash10-0udi-0859000000-8fb5cc787a664fd76c34	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 20V, Positive-QTOF	splash10-0690-1950000000-7ae3b12589c277c0e377	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 40V, Positive-QTOF	splash10-0a4l-2940000000-bfd4fbb4059ae278438f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 10V, Negative-QTOF	splash10-0udi-0039000000-7d394202ae81237c33a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 20V, Negative-QTOF	splash10-0udi-0393000000-63ea158a62162e087ae0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterodiol 40V, Negative-QTOF	splash10-0r13-0890000000-72542e20683700bfc0c2	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected and Quantified	0.00152 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.0015 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.000992 uM	Adult (>18 years old)	Female	Normal	15159299	details
Blood	Detected and Quantified	0.0014 uM	Adult (>18 years old)	Both	Normal	17449591	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.0247 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0140 (0.0120-0.0163) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.0501 +/- 0.100 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	0.0373 +/- 0.0560 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.0240 +/- 0.0240 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.447 +/- 1.00667 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17353586	details
Urine	Detected and Quantified	0.0108 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	17976571	details
Urine	Detected and Quantified	0.0800 +/- 0.100 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.0833 +/- 0.229 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.133 +/- 0.220 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.0211 umol/mmol creatinine	Children (1 - 13 years old)	Female	Normal	17366830	details
Urine	Detected and Quantified	0.0258 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	15159299	details
Urine	Detected and Quantified	0.0339 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22493748	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	10798213	details
Urine	Detected and Quantified	0.032 +/- 0.072 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.013 +/- 0.019 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.065 +/- 0.039 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.013 +/- 0.019 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.0065 +/- 0.019 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.00 +/- 0.0065 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.0065 +/- 0.0065 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	19333587	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	8017326	details
Urine	Detected and Quantified	0.0176 (0.0140-0.0222) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	10952094	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	10075344	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	10527518	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	17499260	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	7722188	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1009	7930998	details
Urine	Detected and Quantified	0.0733 +/-0.04 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.0533 +/- 0.0266 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.01 (0.0 -0.3) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	17976571	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.05 +/- 0.12 umol/mmol creatinine	Adult (>18 years old)	Female	Breast cancer	17403619	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Grace PB, Mistry NS, Carter MH, Leathem AJ, Teale P: High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS). J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jun 15;853(1-2):138-46. Epub 2007 Mar 18. [PubMed:17403619 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enterodiol

METLIN ID

Not Available

PubChem Compound

115089

PDB ID

Not Available

ChEBI ID

544560

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000467

Good Scents ID

Not Available

References

Synthesis Reference

Mahalanabis, K. K.; Mumtax, M.; Snieckuz, V. Dimetalated tertiary succinamides. Synthesis of several classes of lignans including the mammalian urinary lignans enterolactone and enterodiol. Tetrahedron Letters (1982), 23(39), 3975-8.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wang LQ: Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309. [PubMed:12270221 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Showing metabocard for Enterodiol (HMDB0005056)

MOL for HMDB0005056 (Enterodiol)

3D MOL for HMDB0005056 (Enterodiol)

3D SDF for HMDB0005056 (Enterodiol)

3D-SDF for HMDB0005056 (Enterodiol)

PDB for HMDB0005056 (Enterodiol)

3D PDB for HMDB0005056 (Enterodiol)

SMILES for HMDB0005056 (Enterodiol)

INCHI for HMDB0005056 (Enterodiol)

Structure for HMDB0005056 (Enterodiol)

3D Structure for HMDB0005056 (Enterodiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra