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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:37:19 UTC

Update Date

2022-03-07 02:57:09 UTC

HMDB ID

HMDB0041703

Secondary Accession Numbers

HMDB41703

Metabolite Identification

Common Name

7-Hydroxyenterolactone

Description

7-Hydroxyenterolactone belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Based on a literature review a significant number of articles have been published on 7-Hydroxyenterolactone.

Structure

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

HMDB0041703
     RDKit          3D
7-Hydroxyenterolactone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.2300   -3.4521   -0.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3552   -2.5551   -0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -2.5279    0.7080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299   -1.8774    0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -0.8748   -0.6211 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4195   -0.5353   -1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5095    0.0578   -0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191   -0.6863   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5091   -0.0507    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    1.3166    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167    2.0639    0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    3.4556    0.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5338    1.4434   -0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247   -1.4436   -1.3390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9942   -0.4053   -1.5840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1134   -0.9930   -2.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169    0.3001   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    1.5692   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    2.2064    1.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    1.5724    2.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6973    0.3029    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5693   -0.3148    2.6081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858   -0.3244    0.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9826   -1.3936    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -2.6391    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    0.0687   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676    0.0952   -2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415   -1.4891   -1.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -1.7758   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -0.6636    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2738    1.8288    1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361    4.0337   -0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242    2.0219   -0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893   -1.8023   -2.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5839    0.3160   -2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0414   -1.9599   -2.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    2.0648   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    3.2020    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    2.0460    2.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1517   -0.8736    3.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540   -1.3278    0.3377 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 14  2  1  0
 23 17  1  0
 13  7  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  6
 15 35  1  6
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
M  END

  Mrv1652307201900102D          

 24 26  0  0  0  0            999 V2000
10001.1086 9999.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9601 9999.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8517 9999.1425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.9998 9999.1425    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
 9998.1402 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
 9998.8460 9998.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7872 9998.7515    0.0000 H   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  0  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
  3 23  1  1  0  0  0
  8 24  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0041703

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1([C@@H](O)C2=CC(O)=CC=C2)[C@H](CC2=CC(O)=CC=C2)COC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O5/c19-14-5-1-3-11(8-14)7-13-10-23-18(22)16(13)17(21)12-4-2-6-15(20)9-12/h1-6,8-9,13,16-17,19-21H,7,10H2/t13-,16-,17+/m1/s1

> <INCHI_KEY>
NRAPUSPCLWHFAN-XYPHTWIQSA-N

> <FORMULA>
C18H18O5

> <MOLECULAR_WEIGHT>
314.337

> <EXACT_MASS>
314.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.677431835233023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.5322214353333337

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.717862079236125

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.109881909985667

> <JCHEM_PKA_STRONGEST_BASIC>
-3.278032972308461

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
84.0695

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S)-3-[(R)-hydroxy(3-hydroxyphenyl)methyl]-4-[(3-hydroxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041703
     RDKit          3D
7-Hydroxyenterolactone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.2300   -3.4521   -0.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3552   -2.5551   -0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -2.5279    0.7080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299   -1.8774    0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -0.8748   -0.6211 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4195   -0.5353   -1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5095    0.0578   -0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191   -0.6863   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5091   -0.0507    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    1.3166    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167    2.0639    0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    3.4556    0.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5338    1.4434   -0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247   -1.4436   -1.3390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9942   -0.4053   -1.5840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1134   -0.9930   -2.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169    0.3001   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    1.5692   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    2.2064    1.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    1.5724    2.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6973    0.3029    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5693   -0.3148    2.6081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858   -0.3244    0.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9826   -1.3936    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -2.6391    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    0.0687   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676    0.0952   -2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415   -1.4891   -1.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -1.7758   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -0.6636    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2738    1.8288    1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361    4.0337   -0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242    2.0219   -0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893   -1.8023   -2.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5839    0.3160   -2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0414   -1.9599   -2.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    2.0648   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    3.2020    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    2.0460    2.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1517   -0.8736    3.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540   -1.3278    0.3377 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 14  2  1  0
 23 17  1  0
 13  7  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  6
 15 35  1  6
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
M  END

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-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
HETATM   23  O   UNK     0    8664.5138663.526   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0    8666.2698664.336   0.000  0.00  0.00           H+0
CONECT    1    9   19                                                       
CONECT    2   21                                                            
CONECT    3    8   16   23                                                  
CONECT    4   14                                                            
CONECT    5    7                                                            
CONECT    6    7   10                                                       
CONECT    7    8    6    5                                                  
CONECT    8    7    9    3   24                                             
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                                                       
CONECT   23    3                                                            
CONECT   24    8                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0041703
HETATM    1  O1  UNL     1      -2.230  -3.452  -0.669  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.355  -2.555  -0.486  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.609  -2.528   0.708  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.630  -1.877   0.450  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.250  -0.875  -0.621  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.420  -0.535  -1.475  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.509   0.058  -0.673  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.519  -0.686  -0.100  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.509  -0.051   0.647  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.518   1.317   0.838  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.517   2.064   0.271  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.465   3.456   0.424  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.534   1.443  -0.469  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.925  -1.444  -1.339  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.994  -0.405  -1.584  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.113  -0.993  -2.220  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.417   0.300  -0.346  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.001   1.569  -0.001  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.406   2.206   1.154  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.267   1.572   2.025  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.697   0.303   1.705  1.00  0.00           C  
HETATM   22  O5  UNL     1      -4.569  -0.315   2.608  1.00  0.00           O  
HETATM   23  C18 UNL     1      -3.286  -0.324   0.547  1.00  0.00           C  
HETATM   24  H1  UNL     1       0.983  -1.394   1.377  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.349  -2.639   0.085  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.073   0.069  -0.120  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.168   0.095  -2.325  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.841  -1.489  -1.909  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.543  -1.776  -0.235  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.288  -0.664   1.084  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.274   1.829   1.411  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.936   4.034  -0.256  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.724   2.022  -0.931  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.589  -1.802  -2.356  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.584   0.316  -2.320  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.041  -1.960  -2.275  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.327   2.065  -0.686  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.079   3.202   1.422  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.608   2.046   2.948  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.152  -0.874   3.353  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.654  -1.328   0.338  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4
CONECT    4    5   24   25
CONECT    5    6   14   26
CONECT    6    7   27   28
CONECT    7    8    8   13
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   13   13
CONECT   12   32
CONECT   13   33
CONECT   14   15   34
CONECT   15   16   17   35
CONECT   16   36
CONECT   17   18   18   23
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   20   21   39
CONECT   21   22   23   23
CONECT   22   40
CONECT   23   41
END

HMDB0041703
     RDKit          3D
7-Hydroxyenterolactone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.2300   -3.4521   -0.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3552   -2.5551   -0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -2.5279    0.7080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299   -1.8774    0.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -0.8748   -0.6211 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4195   -0.5353   -1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5095    0.0578   -0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191   -0.6863   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5091   -0.0507    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    1.3166    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167    2.0639    0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4649    3.4556    0.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5338    1.4434   -0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247   -1.4436   -1.3390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9942   -0.4053   -1.5840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1134   -0.9930   -2.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4169    0.3001   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    1.5692   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062    2.2064    1.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665    1.5724    2.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6973    0.3029    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5693   -0.3148    2.6081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858   -0.3244    0.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9826   -1.3936    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -2.6391    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    0.0687   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676    0.0952   -2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415   -1.4891   -1.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -1.7758   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -0.6636    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2738    1.8288    1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361    4.0337   -0.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242    2.0219   -0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893   -1.8023   -2.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5839    0.3160   -2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0414   -1.9599   -2.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    2.0648   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    3.2020    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    2.0460    2.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1517   -0.8736    3.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540   -1.3278    0.3377 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 14  2  1  0
 23 17  1  0
 13  7  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  6
 15 35  1  6
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(7R)-Hydroxyenterolactone	HMDB
7-Hydroxyenterolactone	HMDB

Chemical Formula

C₁₈H₁₈O₅

Average Molecular Weight

314.337

Monoisotopic Molecular Weight

314.11542368

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@]1([C@@H](O)C2=CC(O)=CC=C2)[C@H](CC2=CC(O)=CC=C2)COC1=O

InChI Identifier

InChI=1S/C18H18O5/c19-14-5-1-3-11(8-14)7-13-10-23-18(22)16(13)17(21)12-4-2-6-15(20)9-12/h1-6,8-9,13,16-17,19-21H,7,10H2/t13-,16-,17+/m1/s1

InChI Key

NRAPUSPCLWHFAN-XYPHTWIQSA-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
Benzenoid
Gamma butyrolactone
Monocyclic benzene moiety
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041703)
Cytoplasm (HMDB: HMDB0041703)

Source

Exogenous

Exogenous (HMDB: HMDB0041703)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.087 g/L	ALOGPS
logP	2.26	ALOGPS
logP	2.53	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.07 m³·mol⁻¹	ChemAxon
Polarizability	31.68 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]+	171.661	30932474
DeepCCS	[M-H]-	169.303	30932474
DeepCCS	[M-2H]-	203.112	30932474
DeepCCS	[M+Na]+	178.025	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxyenterolactone	[H][C@]1([C@@H](O)C2=CC(O)=CC=C2)[C@H](CC2=CC(O)=CC=C2)COC1=O	4453.6	Standard polar	33892256
7-Hydroxyenterolactone	[H][C@]1([C@@H](O)C2=CC(O)=CC=C2)[C@H](CC2=CC(O)=CC=C2)COC1=O	3055.1	Standard non polar	33892256
7-Hydroxyenterolactone	[H][C@]1([C@@H](O)C2=CC(O)=CC=C2)[C@H](CC2=CC(O)=CC=C2)COC1=O	3175.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxyenterolactone,1TMS,isomer #1	C[Si](C)(C)O[C@@H](C1=CC=CC(O)=C1)[C@@H]1C(=O)OC[C@H]1CC1=CC=CC(O)=C1	2898.0	Semi standard non polar	33892256
7-Hydroxyenterolactone,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC([C@H](O)[C@@H]2C(=O)OC[C@H]2CC2=CC=CC(O)=C2)=C1	2936.3	Semi standard non polar	33892256
7-Hydroxyenterolactone,1TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2[C@@H](O)C2=CC=CC(O)=C2)=C1	2942.5	Semi standard non polar	33892256
7-Hydroxyenterolactone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC([C@H](O[Si](C)(C)C)[C@@H]2C(=O)OC[C@H]2CC2=CC=CC(O)=C2)=C1	2863.9	Semi standard non polar	33892256
7-Hydroxyenterolactone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2[C@@H](O[Si](C)(C)C)C2=CC=CC(O)=C2)=C1	2859.3	Semi standard non polar	33892256
7-Hydroxyenterolactone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2[C@@H](O)C2=CC=CC(O[Si](C)(C)C)=C2)=C1	2986.3	Semi standard non polar	33892256
7-Hydroxyenterolactone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2[C@@H](O[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2)=C1	2967.9	Semi standard non polar	33892256
7-Hydroxyenterolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](C1=CC=CC(O)=C1)[C@@H]1C(=O)OC[C@H]1CC1=CC=CC(O)=C1	3155.5	Semi standard non polar	33892256
7-Hydroxyenterolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@H](O)[C@@H]2C(=O)OC[C@H]2CC2=CC=CC(O)=C2)=C1	3185.7	Semi standard non polar	33892256
7-Hydroxyenterolactone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2[C@@H](O)C2=CC=CC(O)=C2)=C1	3184.6	Semi standard non polar	33892256
7-Hydroxyenterolactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC([C@H](O[Si](C)(C)C(C)(C)C)[C@@H]2C(=O)OC[C@H]2CC2=CC=CC(O)=C2)=C1	3368.2	Semi standard non polar	33892256
7-Hydroxyenterolactone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC(O)=C2)=C1	3355.6	Semi standard non polar	33892256
7-Hydroxyenterolactone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2[C@@H](O)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)=C1	3440.4	Semi standard non polar	33892256
7-Hydroxyenterolactone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H]2COC(=O)[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)=C1	3660.2	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 - 7-Hydroxyenterolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxyenterolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxyenterolactone 10V, Negative-QTOF	splash10-03di-0019000000-12a45b7aa5710d247596	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxyenterolactone 20V, Negative-QTOF	splash10-03dl-3966000000-3f4f5ac0f11f3aed3268	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxyenterolactone 40V, Negative-QTOF	splash10-0006-5590000000-7cac4258dd10f6471c37	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxyenterolactone 10V, Positive-QTOF	splash10-014i-0249000000-8d56a10484ff1e49933f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxyenterolactone 20V, Positive-QTOF	splash10-05fr-5961000000-a346874343a8ce049506	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxyenterolactone 40V, Positive-QTOF	splash10-0694-9410000000-2d3a3b16ef6f3b8885ef	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156908056

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
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 7-Hydroxyenterolactone (HMDB0041703)

MOL for HMDB0041703 (7-Hydroxyenterolactone)

3D MOL for HMDB0041703 (7-Hydroxyenterolactone)

3D SDF for HMDB0041703 (7-Hydroxyenterolactone)

3D-SDF for HMDB0041703 (7-Hydroxyenterolactone)

PDB for HMDB0041703 (7-Hydroxyenterolactone)

3D PDB for HMDB0041703 (7-Hydroxyenterolactone)

SMILES for HMDB0041703 (7-Hydroxyenterolactone)

INCHI for HMDB0041703 (7-Hydroxyenterolactone)

Structure for HMDB0041703 (7-Hydroxyenterolactone)

3D Structure for HMDB0041703 (7-Hydroxyenterolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra