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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:32 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031799

Secondary Accession Numbers

HMDB31799

Metabolite Identification

Common Name

Malonoben

Description

Malonoben belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Based on a literature review a significant number of articles have been published on Malonoben.

Structure

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

HMDB0031799
     RDKit          3D
Malonoben
 43 43  0  0  0  0  0  0  0  0999 V2000
    3.1673    1.2504   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650   -0.0210   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -0.7584   -2.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0468   -0.8549    0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799    0.1948   -0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5161    1.4892   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7859    1.7259    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2673    3.0810    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5822    3.9846    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    5.2885    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229    6.3497    1.5548 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    3.6852    1.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7660    3.4498    2.2050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6590    0.6658    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -0.6195    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -1.7778    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5041   -1.2940    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2798   -2.5314   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6400   -2.7064    1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1178   -0.8543   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996   -2.1599   -0.3575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794    1.8883   -1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489    0.9580   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    1.7590    0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103   -0.1021   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394   -1.0135   -2.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1521   -1.6484   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2867   -1.1997    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511   -0.1999    0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491   -1.7245   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108    2.2793   -0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    3.3608    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6943    0.8815    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -2.1513    0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911   -0.6067    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3847   -0.7496    1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2759   -1.7350   -1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4421   -3.2281   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692   -3.0069   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830   -3.0283    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043   -2.1875    2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2136   -3.6028    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712   -2.5301   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  3  0
  9 12  1  0
 12 13  3  0
  7 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  8 32  1  0
 14 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
M  END


  Mrv0541 05061306082D          

 21 21  0  0  0  0            999 V2000
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -1.1270    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
   -0.3020   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.3020    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
    1.4289    0.8250    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
    1.4289    3.3000    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
    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
    1.4289    0.0000    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    1.4289    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17  1  1  0  0  0  0
 17  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  0  0  0  0
 18  5  1  0  0  0  0
 18  6  1  0  0  0  0
 18 15  1  0  0  0  0
 19 10  3  0  0  0  0
 20 11  3  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031799

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3

> <INCHI_KEY>
MZOPWQKISXCCTP-UHFFFAOYSA-N

> <FORMULA>
C18H22N2O

> <MOLECULAR_WEIGHT>
282.3801

> <EXACT_MASS>
282.173213336

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.572127410880555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
4.959107634666667

> <ALOGPS_LOGS>
-4.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.793973103221765

> <JCHEM_PKA_STRONGEST_BASIC>
-6.79058885963621

> <JCHEM_POLAR_SURFACE_AREA>
67.81

> <JCHEM_REFRACTIVITY>
86.4055

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031799
     RDKit          3D
Malonoben
 43 43  0  0  0  0  0  0  0  0999 V2000
    3.1673    1.2504   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650   -0.0210   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -0.7584   -2.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0468   -0.8549    0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799    0.1948   -0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5161    1.4892   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7859    1.7259    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2673    3.0810    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5822    3.9846    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    5.2885    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229    6.3497    1.5548 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    3.6852    1.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7660    3.4498    2.2050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6590    0.6658    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -0.6195    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -1.7778    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5041   -1.2940    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2798   -2.5314   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6400   -2.7064    1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1178   -0.8543   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996   -2.1599   -0.3575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794    1.8883   -1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489    0.9580   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    1.7590    0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103   -0.1021   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394   -1.0135   -2.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1521   -1.6484   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2867   -1.1997    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511   -0.1999    0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491   -1.7245   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108    2.2793   -0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    3.3608    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6943    0.8815    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -2.1513    0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911   -0.6067    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3847   -0.7496    1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2759   -1.7350   -1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4421   -3.2281   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692   -3.0069   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830   -3.0283    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043   -2.1875    2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2136   -3.6028    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712   -2.5301   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  3  0
  9 12  1  0
 12 13  3  0
  7 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  8 32  1  0
 14 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  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       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.771   0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.231  -2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.564  -2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.104   0.564   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667   7.700   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       5.335   3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6   18                                                            
CONECT    7   12   13                                                       
CONECT    8   12   14                                                       
CONECT    9   12   15                                                       
CONECT   10   13   19                                                       
CONECT   11   13   20                                                       
CONECT   12    7    8    9                                                  
CONECT   13    7   10   11                                                  
CONECT   14    8   16   17                                                  
CONECT   15    9   16   18                                                  
CONECT   16   14   15   21                                                  
CONECT   17    1    2    3   14                                             
CONECT   18    4    5    6   15                                             
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   16                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0031799
HETATM    1  C1  UNL     1       3.167   1.250  -0.823  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.365  -0.021  -0.690  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.530  -0.758  -2.014  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.047  -0.855   0.372  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.980   0.195  -0.311  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.516   1.489  -0.090  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.786   1.726   0.278  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.267   3.081   0.529  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.582   3.985   1.195  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.150   5.289   1.384  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.623   6.350   1.555  1.00  0.00           N  
HETATM   12  C11 UNL     1       0.710   3.685   1.737  1.00  0.00           C  
HETATM   13  N2  UNL     1       1.766   3.450   2.205  1.00  0.00           N  
HETATM   14  C12 UNL     1      -1.659   0.666   0.433  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.212  -0.620   0.218  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.127  -1.778   0.379  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.504  -1.294   0.783  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.280  -2.531  -0.925  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.640  -2.706   1.502  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.118  -0.854  -0.157  1.00  0.00           C  
HETATM   21  O1  UNL     1       0.500  -2.160  -0.357  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.679   1.888  -1.598  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.149   0.958  -1.291  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.403   1.759   0.104  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.010  -0.102  -2.797  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.539  -1.014  -2.447  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.152  -1.648  -1.948  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.287  -1.200   1.107  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.751  -0.200   0.945  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.549  -1.724  -0.066  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.211   2.279  -0.227  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.244   3.361   0.146  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.694   0.882   0.727  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.168  -2.151   0.986  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.891  -0.607   0.011  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.385  -0.750   1.743  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.276  -1.735  -1.724  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.442  -3.228  -1.097  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.269  -3.007  -0.962  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.483  -3.028   2.134  1.00  0.00           H  
HETATM   41  H20 UNL     1      -0.904  -2.187   2.141  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.214  -3.603   1.024  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.371  -2.530  -0.621  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    5
CONECT    3   25   26   27
CONECT    4   28   29   30
CONECT    5    6    6   20
CONECT    6    7   31
CONECT    7    8   14   14
CONECT    8    9    9   32
CONECT    9   10   12
CONECT   10   11   11   11
CONECT   12   13   13   13
CONECT   14   15   33
CONECT   15   16   20   20
CONECT   16   17   18   19
CONECT   17   34   35   36
CONECT   18   37   38   39
CONECT   19   40   41   42
CONECT   20   21
CONECT   21   43
END

HMDB0031799
     RDKit          3D
Malonoben
 43 43  0  0  0  0  0  0  0  0999 V2000
    3.1673    1.2504   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650   -0.0210   -0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -0.7584   -2.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0468   -0.8549    0.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799    0.1948   -0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5161    1.4892   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7859    1.7259    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2673    3.0810    0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5822    3.9846    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    5.2885    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229    6.3497    1.5548 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    3.6852    1.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7660    3.4498    2.2050 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6590    0.6658    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -0.6195    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -1.7778    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5041   -1.2940    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2798   -2.5314   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6400   -2.7064    1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1178   -0.8543   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996   -2.1599   -0.3575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794    1.8883   -1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489    0.9580   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    1.7590    0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103   -0.1021   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394   -1.0135   -2.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1521   -1.6484   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2867   -1.1997    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511   -0.1999    0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491   -1.7245   -0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108    2.2793   -0.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    3.3608    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6943    0.8815    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -2.1513    0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911   -0.6067    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3847   -0.7496    1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2759   -1.7350   -1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4421   -3.2281   -1.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692   -3.0069   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830   -3.0283    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043   -2.1875    2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2136   -3.6028    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712   -2.5301   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  3  0
  9 12  1  0
 12 13  3  0
  7 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  8 32  1  0
 14 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3,5-Di-t-butyl-4-hydroxybenzylidene)malononitrile	HMDB
(3,5-Di-tert-butyl-4-hydroxy-benzylidene)malononitrile	HMDB
(3,5-Di-tert-butyl-4-hydroxybenzylidene)-malononitrile	HMDB
2,6-Di-tert-butyl-4-(2,2-dicyanovinyl)phenol	HMDB
2-(3,5-Di-tert-butyl-4-hydroxybenzylidene)malononitrile	HMDB
3,5-Di-t-butyl-4-hydroxy-benzylidenemalononitrile	HMDB
3,5-Di-tert-butyl-4-hydroxybenzilidenemalononitrile	HMDB
3,5-Di-tert-butyl-4-hydroxybenzylidene-malononitrile	HMDB
SF 6847	HMDB
[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]propanedinitrile, 9ci	HMDB
Tyrphostin a9	MeSH

Chemical Formula

C₁₈H₂₂N₂O

Average Molecular Weight

282.3801

Monoisotopic Molecular Weight

282.173213336

IUPAC Name

2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile

Traditional Name

2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile

CAS Registry Number

10537-47-0

SMILES

CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C

InChI Identifier

InChI=1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3

InChI Key

MZOPWQKISXCCTP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Phenol
Nitrile
Carbonitrile
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alkylbenzene (CHEBI:82168 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031799)
Cell membrane (HMDB: HMDB0031799)

Source

Exogenous

Exogenous (HMDB: HMDB0031799)

Food

Food (HMDB: HMDB0031799)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 - 143 °C	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	0.0056 g/L	ALOGPS
logP	5.47	ALOGPS
logP	4.96	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	8.79	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.41 m³·mol⁻¹	ChemAxon
Polarizability	32.57 Å³	ChemAxon
Number of Rings	1	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]+	169.685	31661259
DarkChem	[M-H]-	167.383	31661259
DeepCCS	[M+H]+	175.353	30932474
DeepCCS	[M-H]-	172.995	30932474
DeepCCS	[M-2H]-	206.634	30932474
DeepCCS	[M+Na]+	181.862	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	160.3	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	173.8	32859911
AllCCS	[M+Na-2H]-	173.7	32859911
AllCCS	[M+HCOO]-	173.8	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.87 minutes	32390414
Predicted by Siyang on May 30, 2022	20.5958 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2803.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	685.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	253.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	376.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	953.6 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	1027.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1500.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	711.7 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	1804.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	513.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	492.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	445.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	390.5 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Malonoben	CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C	3059.9	Standard polar	33892256
Malonoben	CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C	1970.3	Standard non polar	33892256
Malonoben	CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C	2299.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Malonoben,1TMS,isomer #1	CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(C(C)(C)C)=C1O[Si](C)(C)C	2270.4	Semi standard non polar	33892256
Malonoben,1TBDMS,isomer #1	CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2488.9	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 - Malonoben GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2190000000-6dc9933ae3f0f35d5761	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonoben GC-MS (1 TMS) - 70eV, Positive	splash10-0079-7398000000-8bdef250059f7c2d37a7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonoben GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonoben 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malonoben LC-ESI-qTof , Positive-QTOF	splash10-000i-3980000000-dc67e28bf67c9f799108	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Malonoben , positive-QTOF	splash10-03dj-0930000000-dd3a00c3026cef3df28c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 10V, Positive-QTOF	splash10-001i-0090000000-8e4c34f669d44a715ff8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 20V, Positive-QTOF	splash10-0560-0090000000-fbca0da0d0a64fb489f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 40V, Positive-QTOF	splash10-0a4i-2290000000-df11bc58a3a41f87aa4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 10V, Negative-QTOF	splash10-001i-0090000000-0cc6ed32a18e26122b25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 20V, Negative-QTOF	splash10-001i-0090000000-51e82b58663f10fbec4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 40V, Negative-QTOF	splash10-0f9t-1190000000-975ed68e963542428b2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 10V, Positive-QTOF	splash10-003r-0090000000-7f246da144c0720c0aa8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 20V, Positive-QTOF	splash10-003r-2190000000-179ba52afb151af6eec3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 40V, Positive-QTOF	splash10-0600-4920000000-5d3748f532e4cf0d77b2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 10V, Negative-QTOF	splash10-001i-0090000000-3a842f545d21389ac050	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 20V, Negative-QTOF	splash10-001i-0090000000-3a842f545d21389ac050	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonoben 40V, Negative-QTOF	splash10-014i-0090000000-0fa50ff501577e67d4ad	2021-09-25	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

FDB008472

KNApSAcK ID

Not Available

Chemspider ID

5412

KEGG Compound ID

C19039

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

SF-6847

METLIN ID

Not Available

PubChem Compound

5614

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Malonoben (HMDB0031799)

MOL for HMDB0031799 (Malonoben)

3D MOL for HMDB0031799 (Malonoben)

3D SDF for HMDB0031799 (Malonoben)

3D-SDF for HMDB0031799 (Malonoben)

PDB for HMDB0031799 (Malonoben)

3D PDB for HMDB0031799 (Malonoben)

SMILES for HMDB0031799 (Malonoben)

INCHI for HMDB0031799 (Malonoben)

Structure for HMDB0031799 (Malonoben)

3D Structure for HMDB0031799 (Malonoben)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra