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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:20:40 UTC

Update Date

2022-03-07 02:56:43 UTC

HMDB ID

HMDB0040762

Secondary Accession Numbers

HMDB40762

Metabolite Identification

Common Name

5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone

Description

5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a small amount of articles have been published on 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone.

Structure

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

HMDB0040762
     RDKit          3D
5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone
 46 47  0  0  0  0  0  0  0  0999 V2000
   -0.4822    1.4508    2.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916    1.0054    1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6621    0.4496    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6094    0.1709   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.1097   -1.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5106   -0.1542   -2.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252   -0.4968   -2.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9513   -0.7476   -3.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -0.5751   -1.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2383   -0.8943   -2.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720   -0.2818   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -0.3507    0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910   -0.0620    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3624    0.5972    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895    0.0545    0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631    0.0063   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    0.1332    0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3737   -0.3739   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180   -0.7579   -1.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834   -1.4376    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990    0.7411    1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    0.8725    2.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    1.1871    2.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9582    1.7303    3.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120    0.7168    2.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023    2.3134    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2757    1.9362    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    0.0824   -3.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532   -1.1691   -2.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.6566   -2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7262   -1.3758    0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2949   -0.7915    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9721   -0.2175    2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093    0.9893    2.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1632    1.6406    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2856    0.2750    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5797    0.5461   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9014    0.1311    1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9940   -0.5711   -1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0805    0.5024   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617    0.0311   -2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5578   -1.6980   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061   -0.9510   -2.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921   -2.4299   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -1.5664    1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771   -1.2079    0.5473 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
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  2  0
  3 16  1  0
 16 17  2  0
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 18 20  1  0
 17 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 23  2  1  0
 15  4  1  0
  1 25  1  0
  1 26  1  0
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 18 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END


  Mrv0541 05061312062D          

 24 25  0  0  0  0            999 V2000
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  9  1  0  0  0  0
 14  8  2  0  0  0  0
 14 10  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16  8  1  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21 17  2  0  0  0  0
 22 18  2  0  0  0  0
 23 19  2  0  0  0  0
 24 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040762

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC(=C(C)C(=O)C1=O)C1=C(C)C(=O)C(=O)C(=C1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O4/c1-9(2)13-7-15(11(5)17(21)19(13)23)16-8-14(10(3)4)20(24)18(22)12(16)6/h7-10H,1-6H3

> <INCHI_KEY>
OTCZINUTVRBSEL-UHFFFAOYSA-N

> <FORMULA>
C20H22O4

> <MOLECULAR_WEIGHT>
326.3863

> <EXACT_MASS>
326.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.73969748694368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-4-[2-methyl-3,4-dioxo-5-(propan-2-yl)cyclohexa-1,5-dien-1-yl]-6-(propan-2-yl)cyclohexa-3,5-diene-1,2-dione

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
4.8362212840000005

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.093411236493909

> <JCHEM_POLAR_SURFACE_AREA>
68.28

> <JCHEM_REFRACTIVITY>
95.64539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-isopropyl-4-(5-isopropyl-2-methyl-3,4-dioxocyclohexa-1,5-dien-1-yl)-3-methylcyclohexa-3,5-diene-1,2-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040762
     RDKit          3D
5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone
 46 47  0  0  0  0  0  0  0  0999 V2000
   -0.4822    1.4508    2.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916    1.0054    1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6621    0.4496    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6094    0.1709   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.1097   -1.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5106   -0.1542   -2.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252   -0.4968   -2.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9513   -0.7476   -3.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -0.5751   -1.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2383   -0.8943   -2.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720   -0.2818   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -0.3507    0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910   -0.0620    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3624    0.5972    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895    0.0545    0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631    0.0063   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    0.1332    0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3737   -0.3739   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180   -0.7579   -1.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834   -1.4376    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990    0.7411    1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    0.8725    2.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    1.1871    2.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9582    1.7303    3.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120    0.7168    2.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023    2.3134    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2757    1.9362    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    0.0824   -3.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532   -1.1691   -2.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.6566   -2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7262   -1.3758    0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2949   -0.7915    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9721   -0.2175    2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093    0.9893    2.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1632    1.6406    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2856    0.2750    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5797    0.5461   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9014    0.1311    1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9940   -0.5711   -1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0805    0.5024   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617    0.0311   -2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5578   -1.6980   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061   -0.9510   -2.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921   -2.4299   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -1.5664    1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771   -1.2079    0.5473 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
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  7  8  2  0
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  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  2  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 23  2  1  0
 15  4  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
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 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
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 16 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5   11                                                            
CONECT    6   12                                                            
CONECT    7   13   15                                                       
CONECT    8   14   16                                                       
CONECT    9    1    2   13                                                  
CONECT   10    3    4   14                                                  
CONECT   11    5   15   17                                                  
CONECT   12    6   16   18                                                  
CONECT   13    7    9   19                                                  
CONECT   14    8   10   20                                                  
CONECT   15    7   11   16                                                  
CONECT   16    8   12   15                                                  
CONECT   17   11   19   21                                                  
CONECT   18   12   20   22                                                  
CONECT   19   13   17   23                                                  
CONECT   20   14   18   24                                                  
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   20                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0040762
HETATM    1  C1  UNL     1      -0.482   1.451   2.193  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.692   1.005   1.416  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.662   0.450   0.220  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.609   0.171  -0.496  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.669  -0.110  -1.789  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.511  -0.154  -2.695  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.925  -0.497  -2.488  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.951  -0.748  -3.706  1.00  0.00           O  
HETATM    9  C8  UNL     1      -3.135  -0.575  -1.701  1.00  0.00           C  
HETATM   10  O2  UNL     1      -4.238  -0.894  -2.226  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.072  -0.282  -0.291  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.267  -0.351   0.548  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.991  -0.062   2.002  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.362   0.597   0.105  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.889   0.054   0.221  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.963   0.006  -0.309  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.142   0.133   0.301  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.374  -0.374  -0.384  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.118  -0.758  -1.819  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.083  -1.438   0.394  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.199   0.741   1.595  1.00  0.00           C  
HETATM   22  O3  UNL     1       4.319   0.873   2.196  1.00  0.00           O  
HETATM   23  C20 UNL     1       1.971   1.187   2.177  1.00  0.00           C  
HETATM   24  O4  UNL     1       1.958   1.730   3.322  1.00  0.00           O  
HETATM   25  H1  UNL     1      -0.812   0.717   2.911  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.102   2.313   2.891  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.276   1.936   1.616  1.00  0.00           H  
HETATM   28  H4  UNL     1       0.104   0.082  -3.768  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.853  -1.169  -2.827  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.228   0.657  -2.548  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.726  -1.376   0.518  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.295  -0.791   2.465  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.972  -0.217   2.538  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.709   0.989   2.175  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.163   1.641   0.451  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.286   0.275   0.635  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.580   0.546  -0.968  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.901   0.131   1.291  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.994  -0.571  -1.220  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.081   0.502  -0.430  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.562   0.031  -2.344  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.558  -1.698  -1.840  1.00  0.00           H  
HETATM   43  H19 UNL     1       5.106  -0.951  -2.334  1.00  0.00           H  
HETATM   44  H20 UNL     1       5.092  -2.430  -0.145  1.00  0.00           H  
HETATM   45  H21 UNL     1       4.667  -1.566   1.406  1.00  0.00           H  
HETATM   46  H22 UNL     1       6.177  -1.208   0.547  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   23
CONECT    3    4   16
CONECT    4    5    5   15
CONECT    5    6    7
CONECT    6   28   29   30
CONECT    7    8    8    9
CONECT    9   10   10   11
CONECT   11   12   15   15
CONECT   12   13   14   31
CONECT   13   32   33   34
CONECT   14   35   36   37
CONECT   15   38
CONECT   16   17   17   39
CONECT   17   18   21
CONECT   18   19   20   40
CONECT   19   41   42   43
CONECT   20   44   45   46
CONECT   21   22   22   23
CONECT   23   24   24
END

HMDB0040762
     RDKit          3D
5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone
 46 47  0  0  0  0  0  0  0  0999 V2000
   -0.4822    1.4508    2.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916    1.0054    1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6621    0.4496    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6094    0.1709   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.1097   -1.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5106   -0.1542   -2.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252   -0.4968   -2.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9513   -0.7476   -3.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -0.5751   -1.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2383   -0.8943   -2.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720   -0.2818   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -0.3507    0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910   -0.0620    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3624    0.5972    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895    0.0545    0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631    0.0063   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    0.1332    0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3737   -0.3739   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180   -0.7579   -1.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834   -1.4376    0.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1990    0.7411    1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    0.8725    2.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    1.1871    2.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9582    1.7303    3.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120    0.7168    2.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023    2.3134    2.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2757    1.9362    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041    0.0824   -3.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532   -1.1691   -2.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.6566   -2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7262   -1.3758    0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2949   -0.7915    2.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9721   -0.2175    2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093    0.9893    2.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1632    1.6406    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2856    0.2750    0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5797    0.5461   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9014    0.1311    1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9940   -0.5711   -1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0805    0.5024   -0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617    0.0311   -2.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5578   -1.6980   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061   -0.9510   -2.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921   -2.4299   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -1.5664    1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771   -1.2079    0.5473 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
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  2  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 23  2  1  0
 15  4  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₄

Average Molecular Weight

326.3863

Monoisotopic Molecular Weight

326.151809192

IUPAC Name

3-methyl-4-[2-methyl-3,4-dioxo-5-(propan-2-yl)cyclohexa-1,5-dien-1-yl]-6-(propan-2-yl)cyclohexa-3,5-diene-1,2-dione

Traditional Name

6-isopropyl-4-(5-isopropyl-2-methyl-3,4-dioxocyclohexa-1,5-dien-1-yl)-3-methylcyclohexa-3,5-diene-1,2-dione

CAS Registry Number

122548-31-6

SMILES

CC(C)C1=CC(=C(C)C(=O)C1=O)C1=C(C)C(=O)C(=O)C(=C1)C(C)C

InChI Identifier

InChI=1S/C20H22O4/c1-9(2)13-7-15(11(5)17(21)19(13)23)16-8-14(10(3)4)20(24)18(22)12(16)6/h7-10H,1-6H3

InChI Key

OTCZINUTVRBSEL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Quinone
O-benzoquinone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040762)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040762)

Source

Endogenous

Endogenous (HMDB: HMDB0040762)

Plant

Plant (HMDB: HMDB0040762)

Animal

Animal (HMDB: HMDB0040762)

Exogenous

Food

Food (HMDB: HMDB0040762)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0040762)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0040762)

Cellular process

Cell signaling (HMDB: HMDB0040762)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0040762)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0040762)

Nutrient

Nutrient (HMDB: HMDB0040762)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040762)

Emulsifier (HMDB: HMDB0040762)

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	0.017 g/L	ALOGPS
logP	3.61	ALOGPS
logP	4.84	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-9.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	68.28 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.65 m³·mol⁻¹	ChemAxon
Polarizability	35.74 Å³	ChemAxon
Number of Rings	2	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]+	176.092	31661259
DarkChem	[M-H]-	171.203	31661259
DeepCCS	[M+H]+	191.73	30932474
DeepCCS	[M-H]-	189.372	30932474
DeepCCS	[M-2H]-	223.693	30932474
DeepCCS	[M+Na]+	199.006	30932474
AllCCS	[M+H]+	176.3	32859911
AllCCS	[M+H-H2O]+	173.2	32859911
AllCCS	[M+NH4]+	179.2	32859911
AllCCS	[M+Na]+	180.0	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	185.9	32859911
AllCCS	[M+HCOO]-	186.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone	CC(C)C1=CC(=C(C)C(=O)C1=O)C1=C(C)C(=O)C(=O)C(=C1)C(C)C	3221.0	Standard polar	33892256
5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone	CC(C)C1=CC(=C(C)C(=O)C1=O)C1=C(C)C(=O)C(=O)C(=C1)C(C)C	2508.5	Standard non polar	33892256
5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone	CC(C)C1=CC(=C(C)C(=O)C1=O)C1=C(C)C(=O)C(=O)C(=C1)C(C)C	2435.6	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 - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-08gi-5197000000-7ce349c27b0b053df17c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 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 - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 10V, Positive-QTOF	splash10-004i-0029000000-64b4180cd3cd077b2832	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 20V, Positive-QTOF	splash10-05r9-4394000000-d954f8cd650abe239296	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 40V, Positive-QTOF	splash10-0a4i-9320000000-ed18b7fde75addd88249	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 10V, Negative-QTOF	splash10-004i-0009000000-0ed2e82a4e2da245172f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 20V, Negative-QTOF	splash10-004i-0029000000-869ddc593afb29bd0061	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 40V, Negative-QTOF	splash10-0aor-5193000000-811bd1b94262b6a2faf4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 10V, Negative-QTOF	splash10-004i-0009000000-976dd6ecdf84064dc4ff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 20V, Negative-QTOF	splash10-004i-0069000000-7e7aad515d19c43ec076	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 40V, Negative-QTOF	splash10-0690-0092000000-0cbcc15a73f3cc81940c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 10V, Positive-QTOF	splash10-056r-0029000000-e892e5dd23ec2fbaeb34	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 20V, Positive-QTOF	splash10-004i-0089000000-c1f3362e6ab65b08cce8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone 40V, Positive-QTOF	splash10-02k9-3391000000-bac6221d7168345f64c7	2021-09-24	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

FDB020578

KNApSAcK ID

C00056672

Chemspider ID

30777509

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14375763

PDB ID

Not Available

ChEBI ID

175173

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone (HMDB0040762)

MOL for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

3D MOL for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

3D SDF for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

3D-SDF for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

PDB for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

3D PDB for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

SMILES for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

INCHI for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

Structure for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

3D Structure for HMDB0040762 (5,5-Diisopropyl-2,2'-dimethylbiphenyl-3,3',4,4'-tetrone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra