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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:34:09 UTC

Update Date

2022-03-07 02:57:06 UTC

HMDB ID

HMDB0041650

Secondary Accession Numbers

HMDB41650

Metabolite Identification

Common Name

2-Hydroxyenterolactone

Description

2-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 very few articles have been published on 2-Hydroxyenterolactone.

Structure

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

HMDB0041650
     RDKit          3D
2-Hydroxyenterolactone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.5275   -3.2819    1.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130   -2.4322    1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884   -2.4866   -0.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350   -1.9772   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.7865    0.4192 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -0.3210    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586    0.0472   -0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926   -0.9268   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0627   -0.6296   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9728    0.6539   -2.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    1.6420   -2.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1711    2.9219   -2.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660    1.3395   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2080   -1.2426    1.6374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0557   -0.1287    2.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0237    0.4722    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    1.6792    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4778    2.3370   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6892    1.7551   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086    0.5610    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3492    0.0899   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -0.0713    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6760   -1.2457    1.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6528   -1.7378   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2149   -2.7904   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339    0.0125   -0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8168    0.6398    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970   -1.0000    1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259   -1.9207   -0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198   -1.4281   -2.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020    0.8891   -3.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396    3.6501   -2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9854    2.0808   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481   -1.5738    2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318   -0.5594    3.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    0.6192    2.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6906    2.1166    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1757    3.2729   -0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3475    2.2663   -1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6890   -0.7666    0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5149   -1.7395    1.4548 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
 22 23  1  0
 14  2  1  0
 22 16  1  0
 13  7  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  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  1
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 23 41  1  0
M  END

  Mrv0541 02271201272D          

 23 25  0  0  0  0            999 V2000
   -0.1499    2.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624    0.8099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2626    0.8099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5175    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020    1.8495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7240    1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9035    0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5680    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -0.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734   -0.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2089    0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088    0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1732   -0.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528   -0.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6582   -1.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583   -1.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -1.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  1  0  0  0
  4  8  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  8 11  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  2  0  0  0  0
  7 19  1  0  0  0  0
 17 21  1  0  0  0  0
 13 22  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041650

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O5/c19-14-5-1-3-11(8-14)7-13-10-23-18(22)15(13)9-12-4-2-6-16(20)17(12)21/h1-6,8,13,15,19-21H,7,9-10H2/t13-,15+/m0/s1

> <INCHI_KEY>
XZCLFXNAFVVPJG-DZGCQCFKSA-N

> <FORMULA>
C18H18O5

> <MOLECULAR_WEIGHT>
314.3325

> <EXACT_MASS>
314.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.35139063275245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
3.303559720666666

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.662366800224886

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.02822025963218

> <JCHEM_PKA_STRONGEST_BASIC>
-5.964043636672508

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
84.68889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041650
     RDKit          3D
2-Hydroxyenterolactone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.5275   -3.2819    1.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130   -2.4322    1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884   -2.4866   -0.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350   -1.9772   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.7865    0.4192 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -0.3210    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586    0.0472   -0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926   -0.9268   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0627   -0.6296   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9728    0.6539   -2.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    1.6420   -2.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1711    2.9219   -2.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660    1.3395   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2080   -1.2426    1.6374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0557   -0.1287    2.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0237    0.4722    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    1.6792    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4778    2.3370   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6892    1.7551   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086    0.5610    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3492    0.0899   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -0.0713    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6760   -1.2457    1.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6528   -1.7378   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2149   -2.7904   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339    0.0125   -0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8168    0.6398    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970   -1.0000    1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259   -1.9207   -0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198   -1.4281   -2.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020    0.8891   -3.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396    3.6501   -2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9854    2.0808   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481   -1.5738    2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318   -0.5594    3.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    0.6192    2.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6906    2.1166    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1757    3.2729   -0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3475    2.2663   -1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6890   -0.7666    0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5149   -1.7395    1.4548 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
 22 23  1  0
 14  2  1  0
 22 16  1  0
 13  7  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  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  1
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 23 41  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.280   3.882   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.526   2.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.050   1.512   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.490   1.512   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.966   2.977   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.990   3.452   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.955   0.266   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.395   0.266   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.085   1.995   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.553   1.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.927   0.427   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.832  -0.819   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.364  -0.658   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.990   0.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.645   1.995   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.550   0.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.923  -0.658   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.392  -0.819   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.487   0.427   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.113   1.834   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.829  -1.904   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.269  -1.904   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.766  -2.226   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    1                                                       
CONECT    6    2                                                            
CONECT    7    3   19                                                       
CONECT    8    4   11                                                       
CONECT    9   10   14                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    8                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13    9                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20    7                                                  
CONECT   20   19   15                                                       
CONECT   21   17                                                            
CONECT   22   13                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0041650
HETATM    1  O1  UNL     1      -1.527  -3.282   1.864  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.913  -2.432   1.184  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.788  -2.487  -0.217  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.535  -1.977  -0.492  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.561  -0.787   0.419  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.952  -0.321   0.760  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.659   0.047  -0.496  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.393  -0.927  -1.135  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.063  -0.630  -2.303  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.973   0.654  -2.799  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.240   1.642  -2.169  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.171   2.922  -2.694  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.566   1.339  -0.992  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.208  -1.243   1.637  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.056  -0.129   2.194  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.024   0.472   1.302  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.651   1.679   0.694  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.478   2.337  -0.187  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.689   1.755  -0.444  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.109   0.561   0.132  1.00  0.00           C  
HETATM   21  O4  UNL     1      -5.349   0.090  -0.215  1.00  0.00           O  
HETATM   22  C18 UNL     1      -3.242  -0.071   1.017  1.00  0.00           C  
HETATM   23  O5  UNL     1      -3.676  -1.246   1.576  1.00  0.00           O  
HETATM   24  H1  UNL     1       0.653  -1.738  -1.552  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.215  -2.790  -0.138  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.034   0.012  -0.076  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.817   0.640   1.336  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.497  -1.000   1.407  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.426  -1.921  -0.694  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.620  -1.428  -2.759  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.502   0.889  -3.720  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.640   3.650  -2.244  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.985   2.081  -0.472  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.548  -1.574   2.427  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.532  -0.559   3.127  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.321   0.619   2.615  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.691   2.117   0.914  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.176   3.273  -0.651  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.347   2.266  -1.137  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.689  -0.767   0.178  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.515  -1.739   1.455  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   35   36
CONECT   16   17   17   22
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   20   39
CONECT   20   21   22   22
CONECT   21   40
CONECT   22   23
CONECT   23   41
END

HMDB0041650
     RDKit          3D
2-Hydroxyenterolactone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.5275   -3.2819    1.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130   -2.4322    1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884   -2.4866   -0.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5350   -1.9772   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.7865    0.4192 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -0.3210    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586    0.0472   -0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3926   -0.9268   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0627   -0.6296   -2.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9728    0.6539   -2.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    1.6420   -2.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1711    2.9219   -2.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660    1.3395   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2080   -1.2426    1.6374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0557   -0.1287    2.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0237    0.4722    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6506    1.6792    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4778    2.3370   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6892    1.7551   -0.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086    0.5610    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3492    0.0899   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -0.0713    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6760   -1.2457    1.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6528   -1.7378   -1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2149   -2.7904   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339    0.0125   -0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8168    0.6398    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970   -1.0000    1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259   -1.9207   -0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198   -1.4281   -2.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020    0.8891   -3.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396    3.6501   -2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9854    2.0808   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481   -1.5738    2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318   -0.5594    3.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3211    0.6192    2.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6906    2.1166    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1757    3.2729   -0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3475    2.2663   -1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6890   -0.7666    0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5149   -1.7395    1.4548 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
 22 23  1  0
 14  2  1  0
 22 16  1  0
 13  7  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  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  1
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₅

Average Molecular Weight

314.3325

Monoisotopic Molecular Weight

314.115423686

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H18O5/c19-14-5-1-3-11(8-14)7-13-10-23-18(22)15(13)9-12-4-2-6-16(20)17(12)21/h1-6,8,13,15,19-21H,7,9-10H2/t13-,15+/m0/s1

InChI Key

XZCLFXNAFVVPJG-DZGCQCFKSA-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
Catechol
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041650)
Cell membrane (HMDB: HMDB0041650)

Source

Exogenous

Exogenous (HMDB: HMDB0041650)

Food

Food (HMDB: HMDB0041650)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041650)

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	0.029 g/L	ALOGPS
logP	2.58	ALOGPS
logP	3.3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-6	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	84.69 m³·mol⁻¹	ChemAxon
Polarizability	32.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.088	31661259
DarkChem	[M-H]-	172.645	31661259
DeepCCS	[M+H]+	175.961	30932474
DeepCCS	[M-H]-	173.603	30932474
DeepCCS	[M-2H]-	207.69	30932474
DeepCCS	[M+Na]+	182.988	30932474
AllCCS	[M+H]+	175.2	32859911
AllCCS	[M+H-H2O]+	171.7	32859911
AllCCS	[M+NH4]+	178.4	32859911
AllCCS	[M+Na]+	179.4	32859911
AllCCS	[M-H]-	177.0	32859911
AllCCS	[M+Na-2H]-	176.6	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyenterolactone	OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=C(O)C(O)=CC=C2)=C1	4623.6	Standard polar	33892256
2-Hydroxyenterolactone	OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=C(O)C(O)=CC=C2)=C1	3114.3	Standard non polar	33892256
2-Hydroxyenterolactone	OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=C(O)C(O)=CC=C2)=C1	3156.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyenterolactone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=CC(O)=C2O)=C1	2927.7	Semi standard non polar	33892256
2-Hydroxyenterolactone,1TMS,isomer #2	C[Si](C)(C)OC1=C(O)C=CC=C1C[C@H]1C(=O)OC[C@@H]1CC1=CC=CC(O)=C1	2923.2	Semi standard non polar	33892256
2-Hydroxyenterolactone,1TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C[C@H]2C(=O)OC[C@@H]2CC2=CC=CC(O)=C2)=C1O	2919.6	Semi standard non polar	33892256
2-Hydroxyenterolactone,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)=C2O)=C1	2932.9	Semi standard non polar	33892256
2-Hydroxyenterolactone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=CC(O)=C2O[Si](C)(C)C)=C1	2958.8	Semi standard non polar	33892256
2-Hydroxyenterolactone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C[C@H]2C(=O)OC[C@@H]2CC2=CC=CC(O)=C2)=C1O[Si](C)(C)C	2902.5	Semi standard non polar	33892256
2-Hydroxyenterolactone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C)=C1	2990.3	Semi standard non polar	33892256
2-Hydroxyenterolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=CC(O)=C2O)=C1	3185.9	Semi standard non polar	33892256
2-Hydroxyenterolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O)C=CC=C1C[C@H]1C(=O)OC[C@@H]1CC1=CC=CC(O)=C1	3170.3	Semi standard non polar	33892256
2-Hydroxyenterolactone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@H]2C(=O)OC[C@@H]2CC2=CC=CC(O)=C2)=C1O	3162.7	Semi standard non polar	33892256
2-Hydroxyenterolactone,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)=C2O)=C1	3426.0	Semi standard non polar	33892256
2-Hydroxyenterolactone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=CC(O)=C2O[Si](C)(C)C(C)(C)C)=C1	3456.9	Semi standard non polar	33892256
2-Hydroxyenterolactone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@H]2C(=O)OC[C@@H]2CC2=CC=CC(O)=C2)=C1O[Si](C)(C)C(C)(C)C	3389.5	Semi standard non polar	33892256
2-Hydroxyenterolactone,3TBDMS,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)=C2O[Si](C)(C)C(C)(C)C)=C1	3661.2	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 - 2-Hydroxyenterolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2910000000-f0620dd06cca6288ae2c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyenterolactone GC-MS (3 TMS) - 70eV, Positive	splash10-01b9-2550940000-2580043d604768a5ee7c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-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 - 2-Hydroxyenterolactone 10V, Positive-QTOF	splash10-014i-0389000000-1c68927da16473eb8024	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 20V, Positive-QTOF	splash10-0ac9-0981000000-d5bbcdece1ef83e86cb5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 40V, Positive-QTOF	splash10-00pl-5910000000-42c0fbe8d6165c0cd9ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 10V, Negative-QTOF	splash10-03di-0019000000-ccde4f6a8b19687ed1b1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 20V, Negative-QTOF	splash10-02t9-0493000000-5a8d3b57442dee301095	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 40V, Negative-QTOF	splash10-0a4i-0930000000-6d9379b74ac43eec6ce3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 10V, Positive-QTOF	splash10-014i-0269000000-5e03ef0f04aea263b9eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 20V, Positive-QTOF	splash10-0aor-4983000000-f4c343fc16b611d56d12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 40V, Positive-QTOF	splash10-0aor-6960000000-7544331fa65fc0d8a1dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 10V, Negative-QTOF	splash10-03di-0109000000-3d9adf3e56cf6a82d232	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 20V, Negative-QTOF	splash10-0bt9-1974000000-432980210b450d4f8874	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyenterolactone 40V, Negative-QTOF	splash10-0006-9420000000-3d8f39970b28fe62a5d8	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029805

KNApSAcK ID

Not Available

Chemspider ID

30777588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753176

PDB ID

Not Available

ChEBI ID

175034

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 ]

Showing metabocard for 2-Hydroxyenterolactone (HMDB0041650)

MOL for HMDB0041650 (2-Hydroxyenterolactone)

3D MOL for HMDB0041650 (2-Hydroxyenterolactone)

3D SDF for HMDB0041650 (2-Hydroxyenterolactone)

3D-SDF for HMDB0041650 (2-Hydroxyenterolactone)

PDB for HMDB0041650 (2-Hydroxyenterolactone)

3D PDB for HMDB0041650 (2-Hydroxyenterolactone)

SMILES for HMDB0041650 (2-Hydroxyenterolactone)

INCHI for HMDB0041650 (2-Hydroxyenterolactone)

Structure for HMDB0041650 (2-Hydroxyenterolactone)

3D Structure for HMDB0041650 (2-Hydroxyenterolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra