MiMeDB: Showing metabocard for Enterolactone (MMDBc0000438)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:45 UTC

Update Date

2024-04-30 19:32:25 UTC

Metabolite ID

MMDBc0000438

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>
MMDBc0000438

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₈H₁₈O₄

Average Mass

298.338

Monoisotopic Mass

298.12050906

IUPAC Name

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

Traditional Name

enterolactone

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human ; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.37	0.45			umol/mmol creatinine	Adult (>18 years old)	Female	Breast cancer	HMDB	17403619
Human Blood	Detected and Quantified	0.0013				uM	Adult (>18 years old)	Female	Normal	HMDB	17538540
Human Blood	Detected and Quantified	0.0041				uM	Adult (>18 years old)	Female	Normal	HMDB	20332276
Human Blood	Detected and Quantified	0.0091				uM	Adult (>18 years old)	Both	Normal	HMDB	12507978
Human Blood	Detected and Quantified	0.0113				uM	Adult (>18 years old)	Both	Normal	HMDB	17449592
Human Blood	Detected and Quantified	0.014				uM	Adult (>18 years old)	Both	Normal	HMDB	11815409
Human Blood	Detected and Quantified	0.0151				uM	Adult (>18 years old)	Female	Normal	HMDB	15159299
Human Blood	Detected and Quantified	0.0178				uM	Adult (>18 years old)	Male	Normal	HMDB	12771325
Human Blood	Detected and Quantified	0.0202				uM	Adult (>18 years old)	Female	Normal	HMDB	9796633
Human Blood	Detected and Quantified	0.0207				uM	Adult (>18 years old)	Female	Normal	HMDB	12771325
Human Blood	Detected and Quantified	0.022				uM	Adult (>18 years old)	Female	Normal	HMDB	17538540
Human Blood	Detected and Quantified	0.0225				uM	Adult (>18 years old)	Female	Normal	HMDB	9796633
Human Urine	Detected and Quantified	0.0999				umol/mmol creatinine	Children (1 - 13 years old)	Female	Normal	HMDB	17366830
Human Urine	Detected and Quantified	0.133				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	22493748
Human Urine	Detected and Quantified	0.139				umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	HMDB	17976571
Human Urine	Detected and Quantified	0.163				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	20332276
Human Urine	Detected and Quantified	0.164				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12507978
Human Urine	Detected and Quantified	0.208				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Urine	Detected and Quantified	0.289				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12507978
Human Urine	Detected and Quantified	0.313				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	15159299
Human Urine	Detected and Quantified	0.71333				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Urine	Detected and Quantified	0.9333				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Blood	Detected and Quantified	0.0137	0.0188			uM	Adult (>18 years old)	Female	Normal	HMDB	15623842
Human Urine	Detected and Quantified	0.092	0.092			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.11	0.072			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.118	0.115			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	10744130
Human Urine	Detected and Quantified	0.12		0.01	1.94	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	17976571
Human Urine	Detected and Quantified	0.169	0.189			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	10744130
Human Urine	Detected and Quantified	0.18	0.13			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.19	0.21			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.23	0.19			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.243	0.306			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	10744130
Human Urine	Detected and Quantified	0.25	0.18			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.310	0.412			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Urine	Detected and Quantified	0.32	0.019			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	10822017
Human Urine	Detected and Quantified	0.44	0.31			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.58	0.019			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	10822017
Human Urine	Detected and Quantified	0.880	1.387			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	17353586
Human Urine	Detected and Quantified	1.0700	0.880			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	1.593	1.773			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	0.0932		0.0796	0.109	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Urine	Detected and Quantified	0.119		0.0966	0.146	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Urine	Detected and Quantified			0.71	1.1	umol/mmol creatinine	Not Specified	Both	Enterolactone Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.65	0.93	umol/mmol creatinine	Not Specified	Both	Enterolactone Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.76	1.1	umol/mmol creatinine	Not Specified	Both	Enterolactone Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.85	1.3	umol/mmol creatinine	Not Specified	Both	Enterolactone Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.79	1.3	umol/mmol creatinine	Not Specified	Both	Enterolactone Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.91	1.3	umol/mmol creatinine	Not Specified	Both	Enterolactone Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23657156
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0006101

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1002/biof.5520120114. [PubMed:11216511 ]
Adlercreutz H: Phyto-oestrogens and cancer. Lancet Oncol. 2002 Jun;3(6):364-73. doi: 10.1016/s1470-2045(02)00777-5. [PubMed:12107024 ]
Wang LQ: Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309. doi: 10.1016/s1570-0232(02)00281-7. [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. doi: 10.1016/j.cca.2005.07.026. Epub 2005 Sep 15. [PubMed:16168401 ]
Koistinen VM (2019). Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510. University of Eastern Finland.

Showing metabocard for Enterolactone (MMDBc0000438)

MOL for #<Metabolite:0x00007f923a3c6710>

3D MOL for #<Metabolite:0x00007f923a3c6710>

3D SDF for #<Metabolite:0x00007f923a3c6710>

3D-SDF for #<Metabolite:0x00007f923a3c6710>

PDB for #<Metabolite:0x00007f923a3c6710>

3D PDB for #<Metabolite:0x00007f923a3c6710>

SMILES for #<Metabolite:0x00007f923a3c6710>

INCHI for #<Metabolite:0x00007f923a3c6710>

Structure for #<Metabolite:0x00007f923a3c6710>

3D Structure for #<Metabolite:0x00007f923a3c6710>