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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:26:42 UTC

Update Date

2022-03-07 03:17:46 UTC

HMDB ID

HMDB0060519

Secondary Accession Numbers

HMDB60519

Metabolite Identification

Common Name

trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene

Description

trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene, also known as trans-dmba-5,6-dihydrodiol, belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene is an extremely weak basic (essentially neutral) compound (based on its pKa). trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene exists in all living organisms, ranging from bacteria to humans. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Structure

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

HMDB0060519
     RDKit          3D
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene
 40 43  0  0  0  0  0  0  0  0999 V2000
    0.9309    2.5977   -0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207    1.1549   -0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.4146    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1813   -0.9835    0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370   -1.6280   -0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999   -3.0858   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897   -0.9188   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4451   -1.5114   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6235   -0.7909   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516    0.5745   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    1.2200   -0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475    0.4584   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673   -1.8216    0.0594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2564   -2.6816   -1.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6823   -1.1832   -0.0448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6197   -1.7532    0.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6668    0.2765    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    0.8323    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0091    2.1878    0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959    2.9857    0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276    2.4320    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    1.0808    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2119    2.9402   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520    2.6897   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761    3.2770    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -3.4276    0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028   -3.4929   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040   -3.6026    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661   -2.5962   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -1.3561   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4660    1.1498   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070    2.2879   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942   -2.5264    0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5420   -2.0915   -1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -1.3287   -1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -1.8179    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8009    0.2371    0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9831    2.6259    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9460    4.0678    0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    3.1072    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 13 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  2  0
 12  2  1  0
 22 17  1  0
 22  3  1  0
 12  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  1
 14 34  1  0
 15 35  1  6
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END


  Mrv0541 05161318262D          

 22 25  0  0  0  0            999 V2000
    1.1758    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    4.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    2.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    4.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758    3.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    4.4466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7159    4.6025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0662    5.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    5.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 12  2  1  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  2  0  0  0  0
 16 15  1  0  0  0  0
 17 11  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  2  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 19 21  1  1  0  0  0
 20 22  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0060519

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2[C@H](O)[C@@H](O)C3=CC=CC=C3C2=C(C)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O2/c1-11-13-7-3-4-8-14(13)12(2)18-17(11)15-9-5-6-10-16(15)19(21)20(18)22/h3-10,19-22H,1-2H3/t19-,20-/m0/s1

> <INCHI_KEY>
SGVWCDYKBWRHKJ-PMACEKPBSA-N

> <FORMULA>
C20H18O2

> <MOLECULAR_WEIGHT>
290.3557

> <EXACT_MASS>
290.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.46424941319404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6S)-7,12-dimethyl-5,6-dihydrotetraphene-5,6-diol

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
4.050100375333333

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.579938858954911

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.134860470114116

> <JCHEM_PKA_STRONGEST_BASIC>
-3.481123812658838

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
88.72999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S)-7,12-dimethyl-5,6-dihydrotetraphene-5,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060519
     RDKit          3D
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene
 40 43  0  0  0  0  0  0  0  0999 V2000
    0.9309    2.5977   -0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207    1.1549   -0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.4146    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1813   -0.9835    0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370   -1.6280   -0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999   -3.0858   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897   -0.9188   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4451   -1.5114   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6235   -0.7909   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516    0.5745   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    1.2200   -0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475    0.4584   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673   -1.8216    0.0594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2564   -2.6816   -1.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6823   -1.1832   -0.0448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6197   -1.7532    0.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6668    0.2765    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    0.8323    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0091    2.1878    0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959    2.9857    0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276    2.4320    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    1.0808    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2119    2.9402   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520    2.6897   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761    3.2770    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -3.4276    0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028   -3.4929   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040   -3.6026    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661   -2.5962   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -1.3561   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4660    1.1498   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070    2.2879   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942   -2.5264    0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5420   -2.0915   -1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -1.3287   -1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -1.8179    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8009    0.2371    0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9831    2.6259    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9460    4.0678    0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    3.1072    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 13 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  2  0
 12  2  1  0
 22 17  1  0
 22  3  1  0
 12  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  1
 14 34  1  0
 15 35  1  6
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       2.195   3.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.179   9.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.342   4.226   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.846   5.681   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.228   3.935   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.236   5.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.830   3.935   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.838   6.845   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.715   4.226   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.732   6.554   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.691   4.808   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.683   7.718   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.179   5.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.326   6.554   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.211   5.681   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.219   6.845   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.699   5.972   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.195   7.427   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.715   8.300   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.203   8.591   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.724   9.464   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.699  10.047   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    3   13                                                       
CONECT    8    4   14                                                       
CONECT    9    5   15                                                       
CONECT   10    6   16                                                       
CONECT   11    1   13   17                                                  
CONECT   12    2   14   18                                                  
CONECT   13    7   11   14                                                  
CONECT   14    8   12   13                                                  
CONECT   15    9   16   17                                                  
CONECT   16   10   15   19                                                  
CONECT   17   11   15   18                                                  
CONECT   18   12   17   20                                                  
CONECT   19   16   20   21                                                  
CONECT   20   18   19   22                                                  
CONECT   21   19                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0060519
HETATM    1  C1  UNL     1       0.931   2.598  -0.336  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.921   1.155  -0.060  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.233   0.415   0.020  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.181  -0.983   0.014  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.037  -1.628  -0.059  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.100  -3.086  -0.041  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.190  -0.919  -0.125  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.445  -1.511  -0.178  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.623  -0.791  -0.226  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.552   0.575  -0.221  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.295   1.220  -0.170  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.148   0.458  -0.126  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.367  -1.822   0.059  1.00  0.00           C  
HETATM   14  O1  UNL     1      -1.256  -2.682  -1.079  1.00  0.00           O  
HETATM   15  C14 UNL     1      -2.682  -1.183  -0.045  1.00  0.00           C  
HETATM   16  O2  UNL     1      -3.620  -1.753   0.849  1.00  0.00           O  
HETATM   17  C15 UNL     1      -2.667   0.277   0.167  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.902   0.832   0.410  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.009   2.188   0.607  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.896   2.986   0.563  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.628   2.432   0.318  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.535   1.081   0.119  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.212   2.940  -1.131  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.852   2.690  -1.090  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.276   3.277   0.410  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.909  -3.428   0.684  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.403  -3.493  -1.025  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.204  -3.603   0.381  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.466  -2.596  -0.185  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.542  -1.356  -0.265  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.466   1.150  -0.258  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.307   2.288  -0.141  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.394  -2.526   0.920  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.542  -2.091  -1.837  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.161  -1.329  -1.055  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.240  -1.818   1.766  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.801   0.237   0.454  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.983   2.626   0.796  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.946   4.068   0.714  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.836   3.107   0.400  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   12
CONECT    3    4   22
CONECT    4    5    5   13
CONECT    5    6    7
CONECT    6   26   27   28
CONECT    7    8    8   12
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   13   14   15   33
CONECT   14   34
CONECT   15   16   17   35
CONECT   16   36
CONECT   17   18   18   22
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   20   21   39
CONECT   21   22   22   40
END

HMDB0060519
     RDKit          3D
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene
 40 43  0  0  0  0  0  0  0  0999 V2000
    0.9309    2.5977   -0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207    1.1549   -0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.4146    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1813   -0.9835    0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370   -1.6280   -0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0999   -3.0858   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897   -0.9188   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4451   -1.5114   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6235   -0.7909   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516    0.5745   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    1.2200   -0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475    0.4584   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673   -1.8216    0.0594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2564   -2.6816   -1.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6823   -1.1832   -0.0448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6197   -1.7532    0.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6668    0.2765    0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    0.8323    0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0091    2.1878    0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8959    2.9857    0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276    2.4320    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    1.0808    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2119    2.9402   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520    2.6897   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761    3.2770    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -3.4276    0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028   -3.4929   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040   -3.6026    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661   -2.5962   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -1.3561   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4660    1.1498   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070    2.2879   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942   -2.5264    0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5420   -2.0915   -1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -1.3287   -1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -1.8179    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8009    0.2371    0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9831    2.6259    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9460    4.0678    0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    3.1072    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 13 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  2  0
 12  2  1  0
 22 17  1  0
 22  3  1  0
 12  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  1
 14 34  1  0
 15 35  1  6
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
trans-DMBA-5,6-dihydrodiol	Kegg

Chemical Formula

C₂₀H₁₈O₂

Average Molecular Weight

290.3557

Monoisotopic Molecular Weight

290.13067982

IUPAC Name

(5S,6S)-7,12-dimethyl-5,6-dihydrotetraphene-5,6-diol

Traditional Name

(5S,6S)-7,12-dimethyl-5,6-dihydrotetraphene-5,6-diol

CAS Registry Number

Not Available

SMILES

CC1=C2[C@H](O)[C@@H](O)C3=CC=CC=C3C2=C(C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C20H18O2/c1-11-13-7-3-4-8-14(13)12(2)18-17(11)15-9-5-6-10-16(15)19(21)20(18)22/h3-10,19-22H,1-2H3/t19-,20-/m0/s1

InChI Key

SGVWCDYKBWRHKJ-PMACEKPBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthalene
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

phenanthrenes (CHEBI:82593 )

Ontology

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	0.0059 g/L	ALOGPS
logP	3.66	ALOGPS
logP	4.05	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.13	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.73 m³·mol⁻¹	ChemAxon
Polarizability	32.46 Å³	ChemAxon
Number of Rings	4	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]+	167.181	31661259
DarkChem	[M-H]-	166.265	31661259
DeepCCS	[M-2H]-	205.084	30932474
DeepCCS	[M+Na]+	180.311	30932474
AllCCS	[M+H]+	170.3	32859911
AllCCS	[M+H-H2O]+	166.7	32859911
AllCCS	[M+NH4]+	173.7	32859911
AllCCS	[M+Na]+	174.7	32859911
AllCCS	[M-H]-	176.4	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	174.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	7.91 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6119 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.86 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2433.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	338.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	506.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	684.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1040.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	464.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1557.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	399.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	279.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	158.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene	CC1=C2[C@H](O)[C@@H](O)C3=CC=CC=C3C2=C(C)C2=CC=CC=C12	3900.4	Standard polar	33892256
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene	CC1=C2[C@H](O)[C@@H](O)C3=CC=CC=C3C2=C(C)C2=CC=CC=C12	2784.2	Standard non polar	33892256
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene	CC1=C2[C@H](O)[C@@H](O)C3=CC=CC=C3C2=C(C)C2=CC=CC=C12	2916.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene,1TMS,isomer #1	CC1=C2C3=CC=CC=C3[C@H](O)[C@@H](O[Si](C)(C)C)C2=C(C)C2=CC=CC=C12	2770.7	Semi standard non polar	33892256
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene,1TMS,isomer #2	CC1=C2C3=CC=CC=C3[C@H](O[Si](C)(C)C)[C@@H](O)C2=C(C)C2=CC=CC=C12	2772.3	Semi standard non polar	33892256
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene,2TMS,isomer #1	CC1=C2C3=CC=CC=C3[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2=C(C)C2=CC=CC=C12	2722.6	Semi standard non polar	33892256
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene,1TBDMS,isomer #1	CC1=C2C3=CC=CC=C3[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C2=C(C)C2=CC=CC=C12	2985.2	Semi standard non polar	33892256
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene,1TBDMS,isomer #2	CC1=C2C3=CC=CC=C3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C2=C(C)C2=CC=CC=C12	2990.5	Semi standard non polar	33892256
trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene,2TBDMS,isomer #1	CC1=C2C3=CC=CC=C3[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2=C(C)C2=CC=CC=C12	3137.4	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 - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-0490000000-b267cff3234a08405ce5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene GC-MS (2 TMS) - 70eV, Positive	splash10-00r2-3019300000-d411b77f042f21b91b1e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene 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 - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene 10V, Positive-QTOF	splash10-0006-0090000000-50918a86e6337daa5c8d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene 20V, Positive-QTOF	splash10-08fu-0390000000-aac92d3bb111dbf5523d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene 40V, Positive-QTOF	splash10-0kdi-1590000000-5783c5e183b7a23d9499	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene 10V, Negative-QTOF	splash10-000i-0090000000-f12b2d0d9279d10da32b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene 20V, Negative-QTOF	splash10-000i-0090000000-d0424171e06c12e58cd2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene 40V, Negative-QTOF	splash10-024r-0090000000-f78765125fed1d405fd5	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

C19607

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12778780

PDB ID

Not Available

ChEBI ID

82593

Food Biomarker Ontology

Not Available

VMH ID

M03038

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Epoxide hydrolase 1

General function:: Involved in catalytic activity
Specific function:: Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:: EPHX1
Uniprot ID:: P07099
Molecular weight:: 52948.48

Reactions

7,12-Dimethylbenz[a]anthracene 5,6-oxide + Water → trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene	details

Showing metabocard for trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene (HMDB0060519)

MOL for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D MOL for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D SDF for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D-SDF for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

PDB for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D PDB for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

SMILES for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

INCHI for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

Structure for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D Structure for HMDB0060519 (trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions