Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:58:58 UTC

Update Date

2022-03-07 02:55:51 UTC

HMDB ID

HMDB0038651

Secondary Accession Numbers

HMDB38651

Metabolite Identification

Common Name

Homoclausenamide

Description

Homoclausenamide belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Homoclausenamide has been detected, but not quantified in, fruits. This could make homoclausenamide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Homoclausenamide.

Structure

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

HMDB0038651
     RDKit          3D
Homoclausenamide
 38 40  0  0  0  0  0  0  0  0999 V2000
    0.0927    3.6334    1.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1970    2.5795    1.0012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.5336    0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226    0.5602    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7929   -0.4317    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8635   -0.4322    0.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698   -1.4147    0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8127   -2.4224   -0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -2.4438   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505   -1.4595   -0.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002    0.4411   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058   -0.5801   -0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -1.4649   -1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288   -2.4090   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -2.4442    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7505   -1.5476    1.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -0.5960    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    1.7476   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300    2.5554   -2.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    2.5079    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312    3.1052    0.3516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    4.5934    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9343    3.7325    2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8309    3.5301    2.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    1.6183    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469    0.3345    1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966   -1.3782    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5790   -3.2045   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6687   -3.2236   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9279   -1.4951   -1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0100    0.1750   -1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757   -1.4542   -2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048   -3.0987   -1.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876   -3.1928    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1003   -1.5968    2.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    0.1068    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754    1.5227   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676    2.0128   -2.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
 10  5  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END


  Mrv0541 05061310342D          

 21 23  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    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
    2.8579    0.0000    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
    0.0000    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
    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
    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
    0.0000    0.8250    0.0000 N   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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038651

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=C(C(C(O)C1=O)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO2/c1-19-12-15(13-8-4-2-5-9-13)16(17(20)18(19)21)14-10-6-3-7-11-14/h2-12,16-17,20H,1H3

> <INCHI_KEY>
INMHUVDZWKKAOF-UHFFFAOYSA-N

> <FORMULA>
C18H17NO2

> <MOLECULAR_WEIGHT>
279.3331

> <EXACT_MASS>
279.125928793

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.061664525418127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-1-methyl-4,5-diphenyl-1,2,3,4-tetrahydropyridin-2-one

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.244223933333334

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.172384490283832

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.726691544918364

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7930540577298677

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
82.28450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-1-methyl-4,5-diphenyl-3,4-dihydropyridin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038651
     RDKit          3D
Homoclausenamide
 38 40  0  0  0  0  0  0  0  0999 V2000
    0.0927    3.6334    1.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1970    2.5795    1.0012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.5336    0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226    0.5602    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7929   -0.4317    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8635   -0.4322    0.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698   -1.4147    0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8127   -2.4224   -0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -2.4438   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505   -1.4595   -0.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002    0.4411   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058   -0.5801   -0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -1.4649   -1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288   -2.4090   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -2.4442    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7505   -1.5476    1.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -0.5960    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    1.7476   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300    2.5554   -2.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    2.5079    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312    3.1052    0.3516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    4.5934    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9343    3.7325    2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8309    3.5301    2.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    1.6183    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469    0.3345    1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966   -1.3782    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5790   -3.2045   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6687   -3.2236   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9279   -1.4951   -1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0100    0.1750   -1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757   -1.4542   -2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048   -3.0987   -1.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876   -3.1928    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1003   -1.5968    2.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    0.1068    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754    1.5227   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676    2.0128   -2.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
 10  5  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    4    5                                                       
CONECT    3    6    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   13                                                       
CONECT    9    5   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7   14                                                       
CONECT   12   15   19                                                       
CONECT   13    8    9   15                                                  
CONECT   14   10   11   16                                                  
CONECT   15   12   13   16                                                  
CONECT   16   14   15   17                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19   21                                                  
CONECT   19    1   12   18                                                  
CONECT   20   17                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0038651
HETATM    1  C1  UNL     1       0.093   3.633   1.987  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.197   2.580   1.001  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.794   1.534   0.896  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.723   0.560   0.008  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.793  -0.432   0.009  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.864  -0.432   0.869  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.870  -1.415   0.822  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.813  -2.422  -0.102  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.751  -2.444  -0.973  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.750  -1.460  -0.920  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.400   0.441  -0.954  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.406  -0.580  -0.560  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.898  -1.465  -1.489  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.829  -2.409  -1.121  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.251  -2.444   0.193  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.750  -1.548   1.128  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.818  -0.596   0.777  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.151   1.748  -1.167  1.00  0.00           C  
HETATM   19  O1  UNL     1       0.530   2.555  -2.118  1.00  0.00           O  
HETATM   20  C18 UNL     1       1.271   2.508   0.083  1.00  0.00           C  
HETATM   21  O2  UNL     1       2.331   3.105   0.352  1.00  0.00           O  
HETATM   22  H1  UNL     1       0.326   4.593   1.450  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.934   3.733   2.370  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.831   3.530   2.807  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.618   1.618   1.623  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.947   0.335   1.604  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.697  -1.378   1.518  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.579  -3.205  -0.167  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.669  -3.224  -1.719  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.928  -1.495  -1.614  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.010   0.175  -1.946  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.576  -1.454  -2.538  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.205  -3.099  -1.871  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.988  -3.193   0.479  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.100  -1.597   2.157  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.422   0.107   1.499  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.175   1.523  -1.528  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.168   2.013  -2.845  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   20
CONECT    3    4    4   25
CONECT    4    5   11
CONECT    5    6    6   10
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   30
CONECT   11   12   18   31
CONECT   12   13   13   17
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   17   36
CONECT   18   19   20   37
CONECT   19   38
CONECT   20   21   21
END

HMDB0038651
     RDKit          3D
Homoclausenamide
 38 40  0  0  0  0  0  0  0  0999 V2000
    0.0927    3.6334    1.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1970    2.5795    1.0012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.5336    0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226    0.5602    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7929   -0.4317    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8635   -0.4322    0.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698   -1.4147    0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8127   -2.4224   -0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -2.4438   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505   -1.4595   -0.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002    0.4411   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058   -0.5801   -0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -1.4649   -1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8288   -2.4090   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -2.4442    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7505   -1.5476    1.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -0.5960    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    1.7476   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300    2.5554   -2.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    2.5079    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312    3.1052    0.3516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    4.5934    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9343    3.7325    2.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8309    3.5301    2.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    1.6183    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469    0.3345    1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966   -1.3782    1.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5790   -3.2045   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6687   -3.2236   -1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9279   -1.4951   -1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0100    0.1750   -1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757   -1.4542   -2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048   -3.0987   -1.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876   -3.1928    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1003   -1.5968    2.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    0.1068    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754    1.5227   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676    2.0128   -2.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  2  1  0
 10  5  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Homoclausenamide	MeSH

Chemical Formula

C₁₈H₁₇NO₂

Average Molecular Weight

279.3331

Monoisotopic Molecular Weight

279.125928793

IUPAC Name

3-hydroxy-1-methyl-4,5-diphenyl-1,2,3,4-tetrahydropyridin-2-one

Traditional Name

3-hydroxy-1-methyl-4,5-diphenyl-3,4-dihydropyridin-2-one

CAS Registry Number

136112-76-0

SMILES

CN1C=C(C(C(O)C1=O)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H17NO2/c1-19-12-15(13-8-4-2-5-9-13)16(17(20)18(19)21)14-10-6-3-7-11-14/h2-12,16-17,20H,1H3

InChI Key

INMHUVDZWKKAOF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Tetrahydropyridine
Monocyclic benzene moiety
Hydropyridine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038651)
Cytoplasm (HMDB: HMDB0038651)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038651)

Source

Exogenous

Food

Food (HMDB: HMDB0038651)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0038651)

Not Available

Nutrient (HMDB: HMDB0038651)

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	298.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.35	ALOGPS
logP	2.24	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.73	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.28 m³·mol⁻¹	ChemAxon
Polarizability	30.06 Å³	ChemAxon
Number of Rings	3	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]+	165.494	31661259
DarkChem	[M-H]-	164.37	31661259
DeepCCS	[M+H]+	165.917	30932474
DeepCCS	[M-H]-	163.559	30932474
DeepCCS	[M-2H]-	196.445	30932474
DeepCCS	[M+Na]+	172.01	30932474
AllCCS	[M+H]+	167.1	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	170.6	32859911
AllCCS	[M+Na]+	171.6	32859911
AllCCS	[M-H]-	171.4	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	170.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Homoclausenamide	CN1C=C(C(C(O)C1=O)C1=CC=CC=C1)C1=CC=CC=C1	3554.4	Standard polar	33892256
Homoclausenamide	CN1C=C(C(C(O)C1=O)C1=CC=CC=C1)C1=CC=CC=C1	2451.4	Standard non polar	33892256
Homoclausenamide	CN1C=C(C(C(O)C1=O)C1=CC=CC=C1)C1=CC=CC=C1	2505.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Homoclausenamide,1TMS,isomer #1	CN1C=C(C2=CC=CC=C2)C(C2=CC=CC=C2)C(O[Si](C)(C)C)C1=O	2419.8	Semi standard non polar	33892256
Homoclausenamide,1TBDMS,isomer #1	CN1C=C(C2=CC=CC=C2)C(C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)C1=O	2644.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Homoclausenamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-3930000000-32beb65a3915a5afb0ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homoclausenamide GC-MS (1 TMS) - 70eV, Positive	splash10-004u-5931000000-c0079d6a8af8fb89e130	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homoclausenamide 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 - Homoclausenamide 10V, Positive-QTOF	splash10-001i-0090000000-9ed95c56e2c5832b5411	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 20V, Positive-QTOF	splash10-001i-0190000000-fc3471dbae5db6bd0a5c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 40V, Positive-QTOF	splash10-000x-4910000000-8b6527ed44334889687c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 10V, Negative-QTOF	splash10-004i-0090000000-d43d4bd0acdc7656a4a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 20V, Negative-QTOF	splash10-004i-1190000000-29257e0f5b81001d07e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 40V, Negative-QTOF	splash10-0a6u-9850000000-64e5085d8c8390e7bd05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 10V, Negative-QTOF	splash10-004i-0090000000-50cc1ea4c83b57b666b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 20V, Negative-QTOF	splash10-004i-0190000000-8eb50b78cd172d3de41c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 40V, Negative-QTOF	splash10-0f89-1920000000-b4f8f7ec2a0fc744c8c3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 10V, Positive-QTOF	splash10-001i-0090000000-f422f41752598800ed47	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 20V, Positive-QTOF	splash10-001i-0290000000-2d7cd1f445ac97de3170	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoclausenamide 40V, Positive-QTOF	splash10-0006-9530000000-c196e71c0d5defebc9c1	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB018046

KNApSAcK ID

Not Available

Chemspider ID

35014623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14157539

PDB ID

Not Available

ChEBI ID

173986

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1870191

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 Homoclausenamide (HMDB0038651)

MOL for HMDB0038651 (Homoclausenamide)

3D MOL for HMDB0038651 (Homoclausenamide)

3D SDF for HMDB0038651 (Homoclausenamide)

3D-SDF for HMDB0038651 (Homoclausenamide)

PDB for HMDB0038651 (Homoclausenamide)

3D PDB for HMDB0038651 (Homoclausenamide)

SMILES for HMDB0038651 (Homoclausenamide)

INCHI for HMDB0038651 (Homoclausenamide)

Structure for HMDB0038651 (Homoclausenamide)

3D Structure for HMDB0038651 (Homoclausenamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra