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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:26:35 UTC

Update Date

2022-03-07 03:17:46 UTC

HMDB ID

HMDB0060517

Secondary Accession Numbers

HMDB60517

Metabolite Identification

Common Name

trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene

Description

trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene, also known as trans-dmba-3,4-dihydrodiol, belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060517
     RDKit          3D
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene
 40 43  0  0  0  0  0  0  0  0999 V2000
    2.3550   -2.8065    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -1.3951    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -0.3307    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884   -0.4899    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9630    0.5971    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    1.8501   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    2.0548    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2128    0.9474    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8155    1.2012    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601    2.5739    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    0.1054    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3927    0.2513    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146   -0.8912    0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6783   -2.1589    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201   -2.2786    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331   -1.1963    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6794   -0.7422    0.1145 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3439   -1.8419   -0.4435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2000    0.5027   -0.4617 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3347    0.8771    0.3014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022    1.6203   -0.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9660    1.5442   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -3.3099   -0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9650   -3.3114    0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294   -2.9719    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -1.4597    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0503    0.4351   -0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0529    2.7354   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    3.0738   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144    2.9626    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110    2.6815    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697    3.3284   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555   -2.9913    0.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -3.2703    0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075   -0.7592    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385   -2.5524    0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046    0.2931   -1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7813    0.0594    0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699    2.6328   -0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    2.4299   -0.4214 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 16  2  1  0
  8  3  1  0
 16 11  1  0
 22 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  1
 18 36  1  0
 19 37  1  6
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END


  Mrv0541 05161318262D          

 22 25  0  0  0  0            999 V2000
    3.6850    0.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    3.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    3.0434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3347    2.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    2.2639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9058    3.1993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
 10  9  2  0  0  0  0
 11  1  1  0  0  0  0
 12  2  1  0  0  0  0
 13  5  2  0  0  0  0
 13 11  1  0  0  0  0
 14  6  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18 10  1  0  0  0  0
 19 12  2  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 18 21  1  1  0  0  0
 20 22  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0060517

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O2/c1-11-13-5-3-4-6-14(13)12(2)19-15(11)7-8-17-16(19)9-10-18(21)20(17)22/h3-10,18,20-22H,1-2H3/t18-,20-/m0/s1

> <INCHI_KEY>
YZIIKMBFHLJAFT-ICSRJNTNSA-N

> <FORMULA>
C20H18O2

> <MOLECULAR_WEIGHT>
290.3557

> <EXACT_MASS>
290.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.024769453305666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S)-7,12-dimethyl-3,4-dihydrotetraphene-3,4-diol

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
4.002267443333333

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.705008986577738

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.172200728784095

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3712707556786334

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
90.36259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S)-7,12-dimethyl-3,4-dihydrotetraphene-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060517
     RDKit          3D
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene
 40 43  0  0  0  0  0  0  0  0999 V2000
    2.3550   -2.8065    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -1.3951    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -0.3307    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884   -0.4899    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9630    0.5971    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    1.8501   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    2.0548    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2128    0.9474    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8155    1.2012    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601    2.5739    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    0.1054    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3927    0.2513    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146   -0.8912    0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6783   -2.1589    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201   -2.2786    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331   -1.1963    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6794   -0.7422    0.1145 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3439   -1.8419   -0.4435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2000    0.5027   -0.4617 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3347    0.8771    0.3014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022    1.6203   -0.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9660    1.5442   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -3.3099   -0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9650   -3.3114    0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294   -2.9719    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -1.4597    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0503    0.4351   -0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0529    2.7354   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    3.0738   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144    2.9626    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110    2.6815    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697    3.3284   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555   -2.9913    0.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -3.2703    0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075   -0.7592    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385   -2.5524    0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046    0.2931   -1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7813    0.0594    0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699    2.6328   -0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    2.4299   -0.4214 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 16  2  1  0
  8  3  1  0
 16 11  1  0
 22 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  1
 18 36  1  0
 19 37  1  6
 20 38  1  0
 21 39  1  0
 22 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       6.879   1.607   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.862   7.427   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.903   5.099   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.399   6.554   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.895   3.935   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.887   6.845   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.854   2.189   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.342   2.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.342   6.554   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.830   6.845   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.374   3.062   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.366   5.972   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.383   4.226   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.879   5.681   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.862   3.353   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.846   5.099   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.838   3.935   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.179   5.681   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.358   4.808   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.326   4.226   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.691   5.972   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.683   3.062   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   13                                                       
CONECT    6    4   14                                                       
CONECT    7    8   15                                                       
CONECT    8    7   17                                                       
CONECT    9   10   16                                                       
CONECT   10    9   18                                                       
CONECT   11    1   13   15                                                  
CONECT   12    2   14   19                                                  
CONECT   13    5   11   14                                                  
CONECT   14    6   12   13                                                  
CONECT   15    7   11   19                                                  
CONECT   16    9   17   19                                                  
CONECT   17    8   16   20                                                  
CONECT   18   10   20   21                                                  
CONECT   19   12   15   16                                                  
CONECT   20   17   18   22                                                  
CONECT   21   18                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0060517
HETATM    1  C1  UNL     1       2.355  -2.807   0.045  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.897  -1.395   0.034  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.725  -0.331   0.037  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.088  -0.490   0.023  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.963   0.597   0.003  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.418   1.850  -0.002  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.031   2.055   0.012  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.213   0.947   0.034  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.816   1.201   0.028  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.360   2.574   0.299  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.001   0.105   0.011  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.393   0.251   0.002  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.215  -0.891   0.032  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.678  -2.159   0.054  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.320  -2.279   0.045  1.00  0.00           C  
HETATM   16  C16 UNL     1       0.533  -1.196   0.021  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.679  -0.742   0.115  1.00  0.00           C  
HETATM   18  O1  UNL     1      -4.344  -1.842  -0.444  1.00  0.00           O  
HETATM   19  C18 UNL     1      -4.200   0.503  -0.462  1.00  0.00           C  
HETATM   20  O2  UNL     1      -5.335   0.877   0.301  1.00  0.00           O  
HETATM   21  C19 UNL     1      -3.302   1.620  -0.485  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.966   1.544  -0.272  1.00  0.00           C  
HETATM   23  H1  UNL     1       1.969  -3.310  -0.872  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.965  -3.311   0.979  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.429  -2.972   0.069  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.551  -1.460   0.026  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.050   0.435  -0.007  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.053   2.735  -0.018  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.682   3.074  -0.019  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.214   2.963   1.037  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.411   2.682   1.111  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.470   3.328  -0.447  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.356  -2.991   0.078  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.158  -3.270   0.055  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.907  -0.759   1.229  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.338  -2.552   0.244  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.605   0.293  -1.484  1.00  0.00           H  
HETATM   38  H16 UNL     1      -5.781   0.059   0.637  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.670   2.633  -0.685  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.442   2.430  -0.421  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   16
CONECT    3    4    8
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9    9
CONECT    9   10   11
CONECT   10   30   31   32
CONECT   11   12   12   16
CONECT   12   13   22
CONECT   13   14   14   17
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   17   18   19   35
CONECT   18   36
CONECT   19   20   21   37
CONECT   20   38
CONECT   21   22   22   39
CONECT   22   40
END

HMDB0060517
     RDKit          3D
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene
 40 43  0  0  0  0  0  0  0  0999 V2000
    2.3550   -2.8065    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -1.3951    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -0.3307    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884   -0.4899    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9630    0.5971    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    1.8501   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    2.0548    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2128    0.9474    0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8155    1.2012    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601    2.5739    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    0.1054    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3927    0.2513    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146   -0.8912    0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6783   -2.1589    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3201   -2.2786    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331   -1.1963    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6794   -0.7422    0.1145 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3439   -1.8419   -0.4435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2000    0.5027   -0.4617 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3347    0.8771    0.3014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022    1.6203   -0.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9660    1.5442   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -3.3099   -0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9650   -3.3114    0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294   -2.9719    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -1.4597    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0503    0.4351   -0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0529    2.7354   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    3.0738   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144    2.9626    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110    2.6815    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697    3.3284   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555   -2.9913    0.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -3.2703    0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075   -0.7592    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385   -2.5524    0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046    0.2931   -1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7813    0.0594    0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699    2.6328   -0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    2.4299   -0.4214 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 16  2  1  0
  8  3  1  0
 16 11  1  0
 22 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  1
 18 36  1  0
 19 37  1  6
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
trans-DMBA-3,4-dihydrodiol	Kegg

Chemical Formula

C₂₀H₁₈O₂

Average Molecular Weight

290.3557

Monoisotopic Molecular Weight

290.13067982

IUPAC Name

(3S,4S)-7,12-dimethyl-3,4-dihydrotetraphene-3,4-diol

Traditional Name

(3S,4S)-7,12-dimethyl-3,4-dihydrotetraphene-3,4-diol

CAS Registry Number

Not Available

SMILES

CC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C20H18O2/c1-11-13-5-3-4-6-14(13)12(2)19-15(11)7-8-17-16(19)9-10-18(21)20(17)22/h3-10,18,20-22H,1-2H3/t18-,20-/m0/s1

InChI Key

YZIIKMBFHLJAFT-ICSRJNTNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

phenanthrol (CHEBI:82518 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060517)

Source

Exogenous

Exogenous (HMDB: HMDB0060517)

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	0.0017 g/L	ALOGPS
logP	3.91	ALOGPS
logP	4	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	-3.4	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	90.36 m³·mol⁻¹	ChemAxon
Polarizability	33.02 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]+	166.236	31661259
DarkChem	[M-H]-	164.262	31661259
DeepCCS	[M-2H]-	206.395	30932474
DeepCCS	[M+Na]+	181.622	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	167.7	32859911
AllCCS	[M+NH4]+	174.7	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	176.8	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	175.3	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.	7.34 minutes	32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.28 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7172 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.87 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2285.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	354.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	125.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	658.2 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	558.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	64.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1122.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	552.2 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	1565.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	260.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.1 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene	CC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C12	4107.7	Standard polar	33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene	CC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C12	2965.9	Standard non polar	33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene	CC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C12	3162.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,1TMS,isomer #1	CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O[Si](C)(C)C)[C@@H](O)C3=CC=C12	3031.0	Semi standard non polar	33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,1TMS,isomer #2	CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O)[C@@H](O[Si](C)(C)C)C3=CC=C12	2986.3	Semi standard non polar	33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,2TMS,isomer #1	CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C3=CC=C12	2947.8	Semi standard non polar	33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,1TBDMS,isomer #1	CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C3=CC=C12	3217.6	Semi standard non polar	33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,1TBDMS,isomer #2	CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C3=CC=C12	3187.6	Semi standard non polar	33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,2TBDMS,isomer #1	CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C3=CC=C12	3348.1	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-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene GC-MS (Non-derivatized) - 70eV, Positive	splash10-08mi-0090000000-8a0befd1db0c6609edc1	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene GC-MS (2 TMS) - 70eV, Positive	splash10-01ba-5009300000-7f9e2570d5488522b868	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-3,4-Dihydro-3,4-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-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 10V, Positive-QTOF	splash10-0006-0090000000-c698bbac912884720033	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 20V, Positive-QTOF	splash10-06r6-0090000000-5124a7412bb55908277c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 40V, Positive-QTOF	splash10-1029-0190000000-aaba1154bc60c670e183	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-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-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 20V, Negative-QTOF	splash10-000i-0090000000-b8bd2cd25f6d727310c2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 40V, Negative-QTOF	splash10-024r-1090000000-35537bdb8ef5014ec034	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

C19490

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156317

PDB ID

Not Available

ChEBI ID

82518

Food Biomarker Ontology

Not Available

VMH ID

M03032

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

1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene + Water → trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene	details

Showing metabocard for trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene (HMDB0060517)

MOL for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D MOL for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D SDF for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D-SDF for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

PDB for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D PDB for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

SMILES for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

INCHI for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

Structure for HMDB0060517 (trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene)

3D Structure for HMDB0060517 (trans-3,4-Dihydro-3,4-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