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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:03:42 UTC

Update Date

2021-09-26 23:15:24 UTC

HMDB ID

HMDB0258470

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-

Description

2-cyano-3-[4-hydroxy-3,5-bis(propan-2-yl)phenyl]prop-2-enimidic acid belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Based on a literature review very few articles have been published on 2-cyano-3-[4-hydroxy-3,5-bis(propan-2-yl)phenyl]prop-2-enimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0258470
     RDKit          3D
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-
 40 40  0  0  0  0  0  0  0  0999 V2000
   -0.5081    2.9944    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127    2.1208    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115    3.0409    0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616    1.1588    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865    1.2872    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3352    0.4357   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7498    0.6617   -0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7478   -0.1231   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893    0.3714   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500    0.7577   -0.8621 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6686   -1.4344    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4170   -1.9464    0.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7171   -2.1569    0.4130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162   -0.5733   -0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7261   -0.7536   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5332   -1.8098   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997   -2.7291   -2.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143   -2.5508   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    0.1320    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817    0.0014    0.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    2.3289    2.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    3.6313    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    3.5788    3.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515    1.5277    2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    2.5893   -0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7610    4.0130    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2513    3.2985    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    2.0732    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    1.6763   -0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -2.7842    0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470   -1.4286    1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081   -1.2812   -1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -1.2782   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -3.0686   -1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645   -2.3704   -3.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097   -3.6740   -2.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3992   -2.3676   -0.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9382   -2.2927    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1969   -3.6625   -0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3015    0.6066    0.8960 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  3  0
  8 11  1  0
 11 12  1  0
 11 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 15 19  2  0
 19 20  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  7 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 16 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
 20 40  1  0
M  END


  Mrv1652309112122042D          

 20 20  0  0  0  0            999 V2000
    0.0000    2.4750    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    2.4750    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
    1.4289   -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
    0.0000    0.0000    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
   -0.7145    1.2375    0.0000 O   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    0.0000    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
    2.1434   -0.4125    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 N   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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14  6  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  3  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258470

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O2/c1-9(2)13-6-11(5-12(8-17)16(18)20)7-14(10(3)4)15(13)19/h5-7,9-10,19H,1-4H3,(H2,18,20)

> <INCHI_KEY>
HMLQHJRJKQDTKW-UHFFFAOYSA-N

> <FORMULA>
C16H20N2O2

> <MOLECULAR_WEIGHT>
272.348

> <EXACT_MASS>
272.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.435363712442026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-cyano-3-[4-hydroxy-3,5-bis(propan-2-yl)phenyl]prop-2-enamide

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.3274552476666663

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.30146543274694

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.387856955900224

> <JCHEM_PKA_STRONGEST_BASIC>
-1.489894199684362

> <JCHEM_POLAR_SURFACE_AREA>
87.11

> <JCHEM_REFRACTIVITY>
80.2982

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-cyano-3-(4-hydroxy-3,5-diisopropylphenyl)prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258470
     RDKit          3D
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-
 40 40  0  0  0  0  0  0  0  0999 V2000
   -0.5081    2.9944    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127    2.1208    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115    3.0409    0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616    1.1588    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865    1.2872    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3352    0.4357   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7498    0.6617   -0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7478   -0.1231   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893    0.3714   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500    0.7577   -0.8621 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6686   -1.4344    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4170   -1.9464    0.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7171   -2.1569    0.4130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162   -0.5733   -0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7261   -0.7536   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5332   -1.8098   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997   -2.7291   -2.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143   -2.5508   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    0.1320    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817    0.0014    0.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    2.3289    2.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    3.6313    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    3.5788    3.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515    1.5277    2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    2.5893   -0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7610    4.0130    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2513    3.2985    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    2.0732    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    1.6763   -0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -2.7842    0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470   -1.4286    1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081   -1.2812   -1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -1.2782   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -3.0686   -1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645   -2.3704   -3.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097   -3.6740   -2.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3992   -2.3676   -0.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9382   -2.2927    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1969   -3.6625   -0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3015    0.6066    0.8960 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  3  0
  8 11  1  0
 11 12  1  0
 11 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 15 19  2  0
 19 20  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  7 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 16 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
 20 40  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.668  -3.850   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0258470
HETATM    1  C1  UNL     1      -0.508   2.994   2.379  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.513   2.121   1.637  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.312   3.041   0.755  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.762   1.159   0.751  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.586   1.287   0.552  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.335   0.436  -0.267  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.750   0.662  -0.483  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.748  -0.123  -0.291  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.089   0.371  -0.608  1.00  0.00           C  
HETATM   10  N1  UNL     1       6.150   0.758  -0.862  1.00  0.00           N  
HETATM   11  C10 UNL     1       3.669  -1.434   0.287  1.00  0.00           C  
HETATM   12  N2  UNL     1       2.417  -1.946   0.728  1.00  0.00           N  
HETATM   13  O1  UNL     1       4.717  -2.157   0.413  1.00  0.00           O  
HETATM   14  C11 UNL     1       0.616  -0.573  -0.883  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.726  -0.754  -0.725  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.533  -1.810  -1.359  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.800  -2.729  -2.248  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.314  -2.551  -0.288  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.417   0.132   0.108  1.00  0.00           C  
HETATM   20  O2  UNL     1      -2.782   0.001   0.311  1.00  0.00           O  
HETATM   21  H1  UNL     1       0.248   2.329   2.825  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.013   3.631   1.633  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.023   3.579   3.185  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.152   1.528   2.287  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.589   2.589  -0.204  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.761   4.013   0.618  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.251   3.298   1.323  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.147   2.073   1.030  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.970   1.676  -0.875  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.992  -2.784   0.320  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.947  -1.429   1.500  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.108  -1.281  -1.557  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.310  -1.278  -1.983  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.185  -3.069  -1.890  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.664  -2.370  -3.290  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.410  -3.674  -2.352  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.399  -2.368  -0.340  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.938  -2.293   0.727  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.197  -3.662  -0.419  1.00  0.00           H  
HETATM   40  H20 UNL     1      -3.302   0.607   0.896  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4   24
CONECT    3   25   26   27
CONECT    4    5    5   19
CONECT    5    6   28
CONECT    6    7   14   14
CONECT    7    8    8   29
CONECT    8    9   11
CONECT    9   10   10   10
CONECT   11   12   13   13
CONECT   12   30   31
CONECT   14   15   32
CONECT   15   16   19   19
CONECT   16   17   18   33
CONECT   17   34   35   36
CONECT   18   37   38   39
CONECT   19   20
CONECT   20   40
END

HMDB0258470
     RDKit          3D
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-
 40 40  0  0  0  0  0  0  0  0999 V2000
   -0.5081    2.9944    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127    2.1208    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3115    3.0409    0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616    1.1588    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865    1.2872    0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3352    0.4357   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7498    0.6617   -0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7478   -0.1231   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893    0.3714   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500    0.7577   -0.8621 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6686   -1.4344    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4170   -1.9464    0.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7171   -2.1569    0.4130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6162   -0.5733   -0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7261   -0.7536   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5332   -1.8098   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997   -2.7291   -2.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143   -2.5508   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    0.1320    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817    0.0014    0.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    2.3289    2.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129    3.6313    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    3.5788    3.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515    1.5277    2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    2.5893   -0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7610    4.0130    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2513    3.2985    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    2.0732    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    1.6763   -0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -2.7842    0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470   -1.4286    1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081   -1.2812   -1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -1.2782   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -3.0686   -1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645   -2.3704   -3.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097   -3.6740   -2.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3992   -2.3676   -0.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9382   -2.2927    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1969   -3.6625   -0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3015    0.6066    0.8960 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  3  0
  8 11  1  0
 11 12  1  0
 11 13  2  0
  6 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 15 19  2  0
 19 20  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  7 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 16 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
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Cyano-3-[4-hydroxy-3,5-bis(propan-2-yl)phenyl]prop-2-enimidate	Generator

Chemical Formula

C₁₆H₂₀N₂O₂

Average Molecular Weight

272.348

Monoisotopic Molecular Weight

272.152477892

IUPAC Name

2-cyano-3-[4-hydroxy-3,5-bis(propan-2-yl)phenyl]prop-2-enamide

Traditional Name

2-cyano-3-(4-hydroxy-3,5-diisopropylphenyl)prop-2-enamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H20N2O2/c1-9(2)13-6-11(5-12(8-17)16(18)20)7-14(10(3)4)15(13)19/h5-7,9-10,19H,1-4H3,(H2,18,20)

InChI Key

HMLQHJRJKQDTKW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid amide
Phenylpropane
Cumene
Phenol
Benzenoid
Monocyclic benzene moiety
Primary carboxylic acid amide
Carboxamide group
Nitrile
Carbonitrile
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	3.56	ALOGPS
logP	3.33	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.3 m³·mol⁻¹	ChemAxon
Polarizability	30.44 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
DeepCCS	[M+H]+	168.435	30932474
DeepCCS	[M-H]-	166.077	30932474
DeepCCS	[M-2H]-	198.962	30932474
DeepCCS	[M+Na]+	174.528	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-	CC(C)C1=CC(C=C(C#N)C(N)=O)=CC(C(C)C)=C1O	3384.0	Standard polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-	CC(C)C1=CC(C=C(C#N)C(N)=O)=CC(C(C)C)=C1O	1989.5	Standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-	CC(C)C1=CC(C=C(C#N)C(N)=O)=CC(C(C)C)=C1O	2511.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N[Si](C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C	2503.8	Semi standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N[Si](C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C	2400.7	Standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N[Si](C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C	3154.9	Standard polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TMS,isomer #2	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC(C(C)C)=C1O	2516.6	Semi standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TMS,isomer #2	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC(C(C)C)=C1O	2321.4	Standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TMS,isomer #2	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC(C(C)C)=C1O	3228.5	Standard polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,3TMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C	2494.8	Semi standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,3TMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C	2341.6	Standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,3TMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C	2998.7	Standard polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TBDMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C(C)(C)C	2900.4	Semi standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TBDMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C(C)(C)C	2802.8	Standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TBDMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C(C)(C)C	3289.7	Standard polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TBDMS,isomer #2	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O	2955.2	Semi standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TBDMS,isomer #2	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O	2736.9	Standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,2TBDMS,isomer #2	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O	3304.0	Standard polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,3TBDMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C(C)(C)C	3129.4	Semi standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,3TBDMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C(C)(C)C	2938.6	Standard non polar	33892256
2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-,3TBDMS,isomer #1	CC(C)C1=CC(C=C(C#N)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(C(C)C)=C1O[Si](C)(C)C(C)(C)C	3230.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-1190000000-2237720deca998ee46ec	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

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KNApSAcK ID

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Chemspider ID

68105238

KEGG Compound ID

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BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

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PDB ID

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ChEBI ID

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Food Biomarker Ontology

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VMH ID

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MarkerDB ID

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Good Scents ID

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References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)- (HMDB0258470)

MOL for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

3D MOL for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

3D SDF for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

3D-SDF for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

PDB for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

3D PDB for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

SMILES for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

INCHI for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

Structure for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

3D Structure for HMDB0258470 (2-Propenamide, 2-cyano-3-(4-hydroxy-3,5-bis(1-methylethyl)phenyl)-)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra