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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 22:56:58 UTC

Update Date

2021-09-14 15:47:58 UTC

HMDB ID

HMDB0006101

Secondary Accession Numbers

HMDB06101

Metabolite Identification

Common Name

Enterolactone

Description

Enterolactone (CAS: 78473-71-9) is a mammalian lignan that has a similar biphenolic structure to lignans from plants. Lignans are compounds with estrogenic properties and are probably the most important source of phytoestrogens in western diets. Mammalian lignans are formed from precursors that are contained mainly in vegetables, whole grain products, and berries, via the action of intestinal microflora. Enterolactone is produced in the colon by the action of bacteria on secoisolariciresinol, matairesinol, and its glycosides. Secoisolariciresinol is converted to enterodiol which is subsequently converted to enterolactone as it passes through the colon. Matairesinol is converted directly to enterolactone. Enterolactone has been shown to possess weakly estrogenic and antiestrogenic activities, and it has been suggested that the high production of this antiestrogenic mammalian lignans in the gut may serve to protect against breast cancer in women and prostate cancer in men; however epidemiological evidence to date is conflicting (PMID: 16168401 , 12270221 , 11216511 , 12107024 ). Enterolactone is a biomarker for the consumption of soybeans and other soy products.

Structure

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

HMDB0006101
     RDKit          3D
Enterolactone
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.2302    0.4131   -2.0842 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1181    0.3250   -1.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    0.7294   -2.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1143   -0.0314   -1.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    0.1677   -0.1161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4850   -0.8632    0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.6768    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6146   -1.3514   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9699   -1.1879   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -0.3564    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0480    0.3174    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8137    1.1502    1.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6971    0.1435    1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -0.1568   -0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5054    0.5460    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9546    0.3319    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5855   -0.8076    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388   -1.0247    1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279   -0.1193    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1378    1.0016   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9127    1.9268   -0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706    1.2248    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8993   -1.0834   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1022    0.3259   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9217    1.1845    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.8731    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644   -0.7551    1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -1.9909   -1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   -1.7167   -1.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7364   -0.2197   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9484    2.1290    1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2127    0.6749    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8194   -1.2674   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.1909    1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.6372    0.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226   -1.5523    1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100   -1.9249    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7921   -0.2860    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3476    2.6907   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3806    2.1345   -0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 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
 14  2  1  0
 22 16  1  0
 13  7  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  6
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
M  END

  Mrv1652307191923442D          

 22 24  0  0  0  0            999 V2000
10001.1086 9999.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9601 9999.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8517 9999.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9998 9999.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.545110000.5782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.991510000.8194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.324110000.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5790 9999.5498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.4040 9999.5498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.658910000.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.140210000.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.425810000.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.711310000.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7112 9999.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4257 9999.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1403 9999.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.534710000.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.820310000.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8203 9999.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5347 9999.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2492 9999.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.249210000.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  9  1  1  1  0  0  0
  8  3  1  6  0  0  0
  7  5  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  3 16  1  0  0  0  0
 14  4  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
  1 19  1  0  0  0  0
 21  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006101

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC(O)=CC=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m1/s1

> <INCHI_KEY>
HVDGDHBAMCBBLR-PBHICJAKSA-N

> <FORMULA>
C18H18O4

> <MOLECULAR_WEIGHT>
298.338

> <EXACT_MASS>
298.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.942419359849175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.607125042333333

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.765099955610825

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.163039070788626

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9640436366683405

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
82.70800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
enterolactone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006101
     RDKit          3D
Enterolactone
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.2302    0.4131   -2.0842 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1181    0.3250   -1.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    0.7294   -2.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1143   -0.0314   -1.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    0.1677   -0.1161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4850   -0.8632    0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.6768    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6146   -1.3514   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9699   -1.1879   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -0.3564    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0480    0.3174    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8137    1.1502    1.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6971    0.1435    1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -0.1568   -0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5054    0.5460    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9546    0.3319    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5855   -0.8076    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388   -1.0247    1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279   -0.1193    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1378    1.0016   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9127    1.9268   -0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706    1.2248    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8993   -1.0834   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1022    0.3259   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9217    1.1845    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.8731    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644   -0.7551    1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -1.9909   -1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   -1.7167   -1.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7364   -0.2197   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9484    2.1290    1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2127    0.6749    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8194   -1.2674   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.1909    1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.6372    0.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226   -1.5523    1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100   -1.9249    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7921   -0.2860    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3476    2.6907   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3806    2.1345   -0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 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
 14  2  1  0
 22 16  1  0
 13  7  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  6
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0    8668.7368665.066   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8674.0598665.066   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8664.5238665.066   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8659.2008665.066   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.9518667.746   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8666.6518668.196   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8665.4058667.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.8818665.826   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.4218665.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.8978667.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.1958667.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.8618668.144   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.5288667.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.5288665.834   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8661.8618665.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.1958665.834   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.3988668.144   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.0658667.374   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.0658665.834   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.3988665.064   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.7328665.834   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.7328667.374   0.000  0.00  0.00           C+0
CONECT    1    9   19                                                       
CONECT    2   21                                                            
CONECT    3    8   16                                                       
CONECT    4   14                                                            
CONECT    5    7                                                            
CONECT    6    7   10                                                       
CONECT    7    8    6    5                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10    1                                                  
CONECT   10    9    6                                                       
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    4                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11    3                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20    1                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22    2                                                  
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0006101
HETATM    1  O1  UNL     1       2.230   0.413  -2.084  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.118   0.325  -1.512  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.060   0.729  -2.179  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.114  -0.031  -1.565  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.741   0.168  -0.116  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.485  -0.863   0.699  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.946  -0.677   0.512  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.615  -1.351  -0.517  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.970  -1.188  -0.703  1.00  0.00           C  
HETATM   10  C8  UNL     1      -5.675  -0.356   0.127  1.00  0.00           C  
HETATM   11  C9  UNL     1      -5.048   0.317   1.144  1.00  0.00           C  
HETATM   12  O3  UNL     1      -5.814   1.150   1.958  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.697   0.144   1.315  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.756  -0.157  -0.170  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.505   0.546   0.906  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.955   0.332   0.714  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.585  -0.808   1.227  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.939  -1.025   1.080  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.728  -0.119   0.416  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.138   1.002  -0.094  1.00  0.00           C  
HETATM   21  O4  UNL     1       5.913   1.927  -0.766  1.00  0.00           O  
HETATM   22  C18 UNL     1       3.771   1.225   0.053  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.899  -1.083  -1.830  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.102   0.326  -1.832  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.922   1.184   0.245  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.220  -1.873   0.374  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.264  -0.755   1.778  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.009  -1.991  -1.137  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.467  -1.717  -1.502  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.736  -0.220  -0.008  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.948   2.129   1.729  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.213   0.675   2.114  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.819  -1.267  -0.091  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.228   0.191   1.914  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.308   1.637   0.801  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.023  -1.552   1.756  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.410  -1.925   1.490  1.00  0.00           H  
HETATM   38  H16 UNL     1       6.792  -0.286   0.298  1.00  0.00           H  
HETATM   39  H17 UNL     1       6.348   2.691  -0.253  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.381   2.135  -0.366  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4
CONECT    4    5   23   24
CONECT    5    6   14   25
CONECT    6    7   26   27
CONECT    7    8    8   13
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11   30
CONECT   11   12   13   13
CONECT   12   31
CONECT   13   32
CONECT   14   15   33
CONECT   15   16   34   35
CONECT   16   17   17   22
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   38
CONECT   20   21   22   22
CONECT   21   39
CONECT   22   40
END

HMDB0006101
     RDKit          3D
Enterolactone
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.2302    0.4131   -2.0842 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1181    0.3250   -1.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    0.7294   -2.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1143   -0.0314   -1.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    0.1677   -0.1161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4850   -0.8632    0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.6768    0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6146   -1.3514   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9699   -1.1879   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -0.3564    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0480    0.3174    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8137    1.1502    1.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6971    0.1435    1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7555   -0.1568   -0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5054    0.5460    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9546    0.3319    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5855   -0.8076    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388   -1.0247    1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279   -0.1193    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1378    1.0016   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9127    1.9268   -0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706    1.2248    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8993   -1.0834   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1022    0.3259   -1.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9217    1.1845    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.8731    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644   -0.7551    1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -1.9909   -1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   -1.7167   -1.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7364   -0.2197   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9484    2.1290    1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2127    0.6749    2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8194   -1.2674   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.1909    1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.6372    0.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226   -1.5523    1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100   -1.9249    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7921   -0.2860    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3476    2.6907   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3806    2.1345   -0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 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
 14  2  1  0
 22 16  1  0
 13  7  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  6
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Bis(3'-hydroxybenzyl)butyrolactone	HMDB
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer	HMDB
HPMF	HMDB
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone	HMDB
BHMDF	HMDB
2,3-BHBB	HMDB
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomer	HMDB
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone	HMDB
(+)-Enterolactone	HMDB
(3S)-trans-Enterolactone	HMDB
(3S,4S)-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanone	HMDB
(3S,4S)-Enterolactone	HMDB
(±)-enterolactone	HMDB
2,3-Bis(3’-hydroxybenzyl)butyrolactone	HMDB
trans-2,3-Bis(3-hydroxybenzyl)-γ-butyrolactone	HMDB
Enterolactone	HMDB

Chemical Formula

C₁₈H₁₈O₄

Average Molecular Weight

298.338

Monoisotopic Molecular Weight

298.12050906

IUPAC Name

(3S,4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

Traditional Name

enterolactone

CAS Registry Number

185254-87-9

SMILES

OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC(O)=CC=C2)=C1

InChI Identifier

InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m1/s1

InChI Key

HVDGDHBAMCBBLR-PBHICJAKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

lignan (CHEBI:81555 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12507978)

Excreta

Biofluid or Excreta

Urine (PMID: 17976571)
Feces (PMID: 27275383)

Cellular substructure

Membrane (HMDB: HMDB0006101)

Source

Endogenous

Endogenous (HMDB: HMDB0006101)

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)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)
Whole grain cereal products (HMDB: HMDB0006101)

Cereals and cereal products (FooDB: FOOD00858)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0006101)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0006101)

Tea

Tea products (HMDB: HMDB0006101)

Fat and oil

Olive oil (HMDB: HMDB0006101)

Fruit

Fruits (HMDB: HMDB0006101)

Vegetable

Vegetables (HMDB: HMDB0006101)

Legumes (HMDB: HMDB0006101)

Nut

Nuts (HMDB: HMDB0006101)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0006101)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Fruits Consumption (MarkerDB: MDB00000481)
Vegetables Consumption (MarkerDB: MDB00000481)
Fruits + Vegetables Consumption (MarkerDB: MDB00000481)
Peach Consumption (MarkerDB: MDB00000481)
Berries Consumption (MarkerDB: MDB00000481)
Fruit Juices Consumption (MarkerDB: MDB00000481)
Ethanol Consumption (MarkerDB: MDB00000481)
Soy Foods Consumption (MarkerDB: MDB00000481)
Fats Consumption (MarkerDB: MDB00000481)
Dark Bread Consumption (MarkerDB: MDB00000481)
Cereals Consumption (MarkerDB: MDB00000481)
Potato Consumption (MarkerDB: MDB00000481)
Dietary Fibre Consumption (MarkerDB: MDB00000481)
Water Soluble Fibre Consumption (MarkerDB: MDB00000481)
Insoluble Fibre Consumption (MarkerDB: MDB00000481)
Coffee + Tea Consumption (MarkerDB: MDB00000481)
Wine Consumption (MarkerDB: MDB00000481)
Beer Consumption (MarkerDB: MDB00000481)
Liquor Consumption (MarkerDB: MDB00000481)
Mushrooms Consumption (MarkerDB: MDB00000481)
Leafy Vegetables Consumption (MarkerDB: MDB00000481)
Lettuce Consumption (MarkerDB: MDB00000481)
Cabbage Family Vegetables Consumption (MarkerDB: MDB00000481)
Gourds Consumption (MarkerDB: MDB00000481)
Walnut Consumption (MarkerDB: MDB00000481)
Avocado Consumption (MarkerDB: MDB00000481)
Legume Family Vegetables Consumption (MarkerDB: MDB00000481)
Onion Family Vegetables Consumption (MarkerDB: MDB00000481)
Banana Consumption (MarkerDB: MDB00000481)
Olive Consumption (MarkerDB: MDB00000481)
Sesame Consumption (MarkerDB: MDB00000481)
Citrus Fruits Consumption (MarkerDB: MDB00000481)
Potato Family Vegetables Consumption (MarkerDB: MDB00000481)
Carrot Family Vegetables Consumption (MarkerDB: MDB00000481)
Grape Consumption (MarkerDB: MDB00000481)
Enterolactone Exposure (MarkerDB: MDB00000481)

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	0.022 g/L	ALOGPS
logP	3.2	ALOGPS
logP	3.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.71 m³·mol⁻¹	ChemAxon
Polarizability	30.94 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
DeepCCS	[M+H]+	174.972	30932474
DeepCCS	[M-H]-	172.614	30932474
DeepCCS	[M-2H]-	206.64	30932474
DeepCCS	[M+Na]+	181.946	30932474
AllCCS	[M+H]+	171.8	32859911
AllCCS	[M+H-H2O]+	168.1	32859911
AllCCS	[M+NH4]+	175.1	32859911
AllCCS	[M+Na]+	176.1	32859911
AllCCS	[M-H]-	174.8	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	174.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Enterolactone	OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC(O)=CC=C2)=C1	4297.0	Standard polar	33892256
Enterolactone	OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC(O)=CC=C2)=C1	2993.0	Standard non polar	33892256
Enterolactone	OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC(O)=CC=C2)=C1	3009.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Enterolactone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC=CC(O)=C2)=C1	2798.1	Semi standard non polar	33892256
Enterolactone,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C[C@@H]2C(=O)OC[C@H]2CC2=CC=CC(O)=C2)=C1	2801.4	Semi standard non polar	33892256
Enterolactone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC=CC(O[Si](C)(C)C)=C2)=C1	2865.8	Semi standard non polar	33892256
Enterolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC=CC(O)=C2)=C1	3046.1	Semi standard non polar	33892256
Enterolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H]2C(=O)OC[C@H]2CC2=CC=CC(O)=C2)=C1	3054.0	Semi standard non polar	33892256
Enterolactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2CC2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)=C1	3317.8	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 - Enterolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2930000000-f09c9cac23beb829be13	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enterolactone 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 - Enterolactone 10V, Positive-QTOF	splash10-000t-0190000000-d33c0fafd73d31bd1204	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 10V, Positive-QTOF	splash10-001j-0980000000-2d1b0924938a24f1eb05	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 30V, Positive-QTOF	splash10-0a59-0900000000-d092c0cfddc526e6ebba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 50V, Positive-QTOF	splash10-0a4i-2920000000-18d6a269cd7da1f4ef15	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 50V, Positive-QTOF	splash10-0a6r-2920000000-4f8142e2478ebf1a5b9d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 30V, Positive-QTOF	splash10-0a59-0910000000-bb995b1188dbee333149	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 10V, Positive-QTOF	splash10-001i-0970000000-8edbf7d5ec7cbb5b2a3b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 10V, Positive-QTOF	splash10-000t-0090000000-639a43db19d283c92d2b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 6V, Positive-QTOF	splash10-001j-0980000000-712c47c7973eea7aa7fe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 30V, Positive-QTOF	splash10-0a59-0900000000-9b12c38f324adb5eeb41	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 50V, Positive-QTOF	splash10-0a6r-2910000000-08b0bae58794f445d83b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 6V, Positive-QTOF	splash10-000t-0090000000-26475d4cba4d01de2031	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 6V, Positive-QTOF	splash10-0a59-0900000000-6f5cc98bcc9de89f5999	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 6V, Positive-QTOF	splash10-0a59-0910000000-b6e9f8b5b9f5ba8ef008	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 6V, Positive-QTOF	splash10-0a59-0900000000-91f736afb6d72e71cc98	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 6V, Positive-QTOF	splash10-001j-0980000000-aea91a6243afbd88af26	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 10V, Positive-QTOF	splash10-000t-0090000000-42cc05f41cd630cc6078	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enterolactone 10V, Positive-QTOF	splash10-001j-0980000000-1082df507fa005706623	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterolactone 10V, Positive-QTOF	splash10-0002-0190000000-642d4c8d3404bc3f1f38	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterolactone 20V, Positive-QTOF	splash10-0a5a-0490000000-0fc8cabcfd095169a527	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterolactone 40V, Positive-QTOF	splash10-014l-4930000000-03f5b31277825fdc664c	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterolactone 10V, Negative-QTOF	splash10-0002-0090000000-c0857d2d2f364ae91560	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterolactone 20V, Negative-QTOF	splash10-0f6t-0190000000-f43dcd7ff2ab06e61ff1	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterolactone 40V, Negative-QTOF	splash10-014r-1950000000-316abee781de19a5a2ba	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enterolactone 10V, Negative-QTOF	splash10-0002-0090000000-184e83ae8436a463dfb8	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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 and Quantified	0.0091 uM	Adult (>18 years old)	Both	Normal	12507978	details
Blood	Detected and Quantified	0.0113 uM	Adult (>18 years old)	Both	Normal	17449592	details
Blood	Detected and Quantified	0.014 uM	Adult (>18 years old)	Both	Normal	11815409	details
Blood	Detected and Quantified	0.0013 uM	Adult (>18 years old)	Female	Normal	17538540	details
Blood	Detected and Quantified	0.0041 uM	Adult (>18 years old)	Female	Normal	20332276	details
Blood	Detected and Quantified	0.0151 uM	Adult (>18 years old)	Female	Normal	15159299	details
Blood	Detected and Quantified	0.0202 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.0207 uM	Adult (>18 years old)	Female	Normal	12771325	details
Blood	Detected and Quantified	0.022 uM	Adult (>18 years old)	Female	Normal	17538540	details
Blood	Detected and Quantified	0.0225 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.0137 +/- 0.0188 uM	Adult (>18 years old)	Female	Normal	15623842	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected and Quantified	0.0178 uM	Adult (>18 years old)	Male	Normal	12771325	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	0.169 +/- 0.189 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.118 +/- 0.115 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.880 +/- 1.387 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17353586	details
Urine	Detected and Quantified	0.139 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	17976571	details
Urine	Detected and Quantified	0.164 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12507978	details
Urine	Detected and Quantified	0.289 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12507978	details
Urine	Detected and Quantified	0.243 +/- 0.306 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	1.0700 +/- 0.880 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	1.593 +/- 1.773 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0999 umol/mmol creatinine	Children (1 - 13 years old)	Female	Normal	17366830	details
Urine	Detected and Quantified	0.12 (0.01-1.94) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	17976571	details
Urine	Detected and Quantified	0.133 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22493748	details
Urine	Detected and Quantified	0.163 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	20332276	details
Urine	Detected and Quantified	0.313 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	15159299	details
Urine	Detected and Quantified	0.9333 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.71333 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.32 +/- 0.019 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10822017	details
Urine	Detected and Quantified	0.58 +/- 0.019 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10822017	details
Urine	Detected and Quantified	0.25 +/- 0.18 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.19 +/- 0.21 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.44 +/- 0.31 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.23 +/- 0.19 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.18 +/- 0.13 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23657156	details
Urine	Detected and Quantified	0.092 +/- 0.092 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.11 +/- 0.072 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.208 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.310 +/- 0.412 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1010	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1010	19333587	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1010	8017326	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1010	10798213	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1010	10952094	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1010	10075344	details
Urine	Detected and Quantified	0.0932 (0.0796-0.109) umol/mmol creatinine	Adult (>18 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 1010	10527518	details
Urine	Detected and Quantified	0.119 (0.0966-0.146) 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 1010	7722188	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 1010	7930998	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Urine	Detected and Quantified	0.37 +/- 0.45 umol/mmol creatinine	Adult (>18 years old)	Female	Breast cancer	17403619	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000703

Chemspider ID

102727

KEGG Compound ID

C18165

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enterolactone

METLIN ID

Not Available

PubChem Compound

114739

PDB ID

Not Available

ChEBI ID

81555

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000481

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]
Boccardo F, Puntoni M, Guglielmini P, Rubagotti A: Enterolactone as a risk factor for breast cancer: a review of the published evidence. Clin Chim Acta. 2006 Mar;365(1-2):58-67. Epub 2005 Sep 15. [PubMed:16168401 ]
Adlercreut H, Mazur W, Stumpf K, Kilkkinen A, Pietinen P, Hulten K, Hallmans G: Food containing phytoestrogens, and breast cancer. Biofactors. 2000;12(1-4):89-93. [PubMed:11216511 ]
Adlercreutz H: Phyto-oestrogens and cancer. Lancet Oncol. 2002 Jun;3(6):364-73. [PubMed:12107024 ]
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 Enterolactone (HMDB0006101)

MOL for HMDB0006101 (Enterolactone)

3D MOL for HMDB0006101 (Enterolactone)

3D SDF for HMDB0006101 (Enterolactone)

3D-SDF for HMDB0006101 (Enterolactone)

PDB for HMDB0006101 (Enterolactone)

3D PDB for HMDB0006101 (Enterolactone)

SMILES for HMDB0006101 (Enterolactone)

INCHI for HMDB0006101 (Enterolactone)

Structure for HMDB0006101 (Enterolactone)

3D Structure for HMDB0006101 (Enterolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra