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 23:58:51 UTC

Update Date

2022-03-07 02:55:51 UTC

HMDB ID

HMDB0038649

Secondary Accession Numbers

HMDB38649

Metabolite Identification

Common Name

(±)-Clausenamide

Description

(±)-Clausenamide belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms (±)-Clausenamide has been detected, but not quantified in, fruits. This could make (±)-clausenamide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-Clausenamide.

Structure

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

HMDB0038649
     RDKit          3D
(±)-Clausenamide
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.7861   -2.4998    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4668   -1.9522   -0.1088 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -2.5643   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3660   -3.6747   -1.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149   -1.6384   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635   -0.8583   -2.2277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -0.9197    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    0.2325    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5647    1.2402   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4120    2.3046   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1760    2.4065    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0720    1.4105    1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250    0.3591    1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -0.7253    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4669    0.4838   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    1.6564    0.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9370    0.5862   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7020    0.2109   -1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    0.2579   -1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014    0.7040    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9365    1.0851    1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5587    1.0345    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -3.5153    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533   -2.6523   -0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -1.8825    0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -2.1880   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912   -1.2893   -2.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060   -1.7037    0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0061    1.2375   -1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5230    3.1161   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8499    3.2590    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6859    1.5104    2.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781   -0.4032    2.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -0.8298    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    0.4975   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767    2.3787    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430   -0.1503   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -0.0386   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7866    0.7492    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    1.4362    2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    1.3289    1.9984 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 14  2  1  0
 22 17  1  0
 13  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

  Mrv0541 02241215132D          

 22 24  0  0  0  0            999 V2000
   -0.5331   -2.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722   -2.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930   -1.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4365   -1.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -1.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0260   -2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791   -1.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156    0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4365    0.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722    1.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1904    2.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4513    2.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870    2.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044    1.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5331    1.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722   -0.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791    0.0409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896    0.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 20  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 18  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038649

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(C(O)C2=CC=CC=C2)C(C(O)C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO3/c1-19-15(16(20)13-10-6-3-7-11-13)14(17(21)18(19)22)12-8-4-2-5-9-12/h2-11,14-17,20-21H,1H3

> <INCHI_KEY>
WGYGSZOQGYRGIP-UHFFFAOYSA-N

> <FORMULA>
C18H19NO3

> <MOLECULAR_WEIGHT>
297.3484

> <EXACT_MASS>
297.136493479

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.09046103050668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-5-[hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.4672396179999998

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.87243267561918

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.744330410821018

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3111373026362703

> <JCHEM_POLAR_SURFACE_AREA>
60.77

> <JCHEM_REFRACTIVITY>
83.35990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-5-[hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038649
     RDKit          3D
(±)-Clausenamide
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.7861   -2.4998    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4668   -1.9522   -0.1088 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -2.5643   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3660   -3.6747   -1.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149   -1.6384   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635   -0.8583   -2.2277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -0.9197    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    0.2325    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5647    1.2402   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4120    2.3046   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1760    2.4065    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0720    1.4105    1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250    0.3591    1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -0.7253    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4669    0.4838   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    1.6564    0.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9370    0.5862   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7020    0.2109   -1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    0.2579   -1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014    0.7040    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9365    1.0851    1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5587    1.0345    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -3.5153    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533   -2.6523   -0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -1.8825    0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -2.1880   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912   -1.2893   -2.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060   -1.7037    0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0061    1.2375   -1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5230    3.1161   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8499    3.2590    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6859    1.5104    2.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781   -0.4032    2.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -0.8298    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    0.4975   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767    2.3787    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430   -0.1503   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -0.0386   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7866    0.7492    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    1.4362    2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    1.3289    1.9984 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 14  2  1  0
 22 17  1  0
 13  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.995  -4.366   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.375  -5.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.754  -4.673   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.907  -3.141   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.681  -2.221   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.149  -2.834   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.915  -3.907   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.454  -2.375   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.076  -1.915   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.076  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.149   0.536   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.681   0.076   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.375   2.987   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.222   4.521   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.842   5.287   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.536   4.366   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.382   2.834   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.995   2.068   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.907  -1.149   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.375  -1.149   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.454   0.076   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.221   1.454   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    9                                                  
CONECT    7    8                                                            
CONECT    8    7    9   20                                                  
CONECT    9    6    8   10                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11                                                            
CONECT   13   14   18                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   11   13   17                                                  
CONECT   19   20                                                            
CONECT   20    8   19   21                                                  
CONECT   21   10   20   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0038649
HETATM    1  C1  UNL     1       1.786  -2.500   0.148  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.467  -1.952  -0.109  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.464  -2.564  -0.983  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.366  -3.675  -1.547  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.615  -1.638  -1.123  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.364  -0.858  -2.228  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.576  -0.920   0.194  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.445   0.233   0.327  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.565   1.240  -0.600  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.412   2.305  -0.396  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.176   2.407   0.744  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.072   1.410   1.683  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.225   0.359   1.465  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.124  -0.725   0.458  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.467   0.484  -0.148  1.00  0.00           C  
HETATM   16  O3  UNL     1      -0.067   1.656   0.381  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.937   0.586  -0.005  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.702   0.211  -1.087  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.079   0.258  -1.085  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.701   0.704   0.062  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.936   1.085   1.160  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.559   1.034   1.149  1.00  0.00           C  
HETATM   23  H1  UNL     1       1.718  -3.515   0.619  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.353  -2.652  -0.792  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.350  -1.883   0.888  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.571  -2.188  -1.280  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.791  -1.289  -2.910  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.906  -1.704   0.952  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.006   1.238  -1.517  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.523   3.116  -1.118  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.850   3.259   0.899  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.686   1.510   2.578  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.178  -0.403   2.237  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.056  -0.830   1.549  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.229   0.498  -1.229  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.577   2.379   0.470  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.243  -0.150  -2.020  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.673  -0.039  -1.940  1.00  0.00           H  
HETATM   39  H17 UNL     1       5.787   0.749   0.086  1.00  0.00           H  
HETATM   40  H18 UNL     1       4.403   1.436   2.066  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.957   1.329   1.998  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   14
CONECT    3    4    4    5
CONECT    5    6    7   26
CONECT    6   27
CONECT    7    8   14   28
CONECT    8    9    9   13
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12   31
CONECT   12   13   13   32
CONECT   13   33
CONECT   14   15   34
CONECT   15   16   17   35
CONECT   16   36
CONECT   17   18   18   22
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   20   21   39
CONECT   21   22   22   40
CONECT   22   41
END

HMDB0038649
     RDKit          3D
(±)-Clausenamide
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.7861   -2.4998    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4668   -1.9522   -0.1088 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -2.5643   -0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3660   -3.6747   -1.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149   -1.6384   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3635   -0.8583   -2.2277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -0.9197    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    0.2325    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5647    1.2402   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4120    2.3046   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1760    2.4065    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0720    1.4105    1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250    0.3591    1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -0.7253    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4669    0.4838   -0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    1.6564    0.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9370    0.5862   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7020    0.2109   -1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    0.2579   -1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014    0.7040    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9365    1.0851    1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5587    1.0345    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -3.5153    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533   -2.6523   -0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -1.8825    0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -2.1880   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912   -1.2893   -2.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060   -1.7037    0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0061    1.2375   -1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5230    3.1161   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8499    3.2590    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6859    1.5104    2.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1781   -0.4032    2.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -0.8298    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    0.4975   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767    2.3787    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430   -0.1503   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734   -0.0386   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7866    0.7492    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    1.4362    2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    1.3289    1.9984 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 14  2  1  0
 22 17  1  0
 13  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO₃

Average Molecular Weight

297.3484

Monoisotopic Molecular Weight

297.136493479

IUPAC Name

3-hydroxy-5-[hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

Traditional Name

3-hydroxy-5-[hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

CAS Registry Number

103541-15-7

SMILES

CN1C(C(O)C2=CC=CC=C2)C(C(O)C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H19NO3/c1-19-15(16(20)13-10-6-3-7-11-13)14(17(21)18(19)22)12-8-4-2-5-9-12/h2-11,14-17,20-21H,1H3

InChI Key

WGYGSZOQGYRGIP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Phenylpyrrolidines

Direct Parent

Phenylpyrrolidines

Alternative Parents

Substituents

3-phenylpyrrolidine
Monocyclic benzene moiety
Pyrrolidone
2-pyrrolidone
Benzenoid
N-alkylpyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Aromatic alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB38649)

Food

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	239 - 240 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1840 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	1.93 g/L	ALOGPS
logP	1.67	ALOGPS
logP	1.47	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.36 m³·mol⁻¹	ChemAxon
Polarizability	31.09 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]+	169.402	31661259
DarkChem	[M-H]-	166.008	31661259
DeepCCS	[M+H]+	167.229	30932474
DeepCCS	[M-H]-	164.871	30932474
DeepCCS	[M-2H]-	197.987	30932474
DeepCCS	[M+Na]+	173.322	30932474
AllCCS	[M+H]+	173.3	32859911
AllCCS	[M+H-H2O]+	169.7	32859911
AllCCS	[M+NH4]+	176.6	32859911
AllCCS	[M+Na]+	177.6	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.4	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Clausenamide	CN1C(C(O)C2=CC=CC=C2)C(C(O)C1=O)C1=CC=CC=C1	3716.7	Standard polar	33892256
(??)-Clausenamide	CN1C(C(O)C2=CC=CC=C2)C(C(O)C1=O)C1=CC=CC=C1	2646.2	Standard non polar	33892256
(??)-Clausenamide	CN1C(C(O)C2=CC=CC=C2)C(C(O)C1=O)C1=CC=CC=C1	2685.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-Clausenamide,1TMS,isomer #1	CN1C(=O)C(O)C(C2=CC=CC=C2)C1C(O[Si](C)(C)C)C1=CC=CC=C1	2427.1	Semi standard non polar	33892256
(??)-Clausenamide,1TMS,isomer #2	CN1C(=O)C(O[Si](C)(C)C)C(C2=CC=CC=C2)C1C(O)C1=CC=CC=C1	2446.6	Semi standard non polar	33892256
(??)-Clausenamide,2TMS,isomer #1	CN1C(=O)C(O[Si](C)(C)C)C(C2=CC=CC=C2)C1C(O[Si](C)(C)C)C1=CC=CC=C1	2470.7	Semi standard non polar	33892256
(??)-Clausenamide,1TBDMS,isomer #1	CN1C(=O)C(O)C(C2=CC=CC=C2)C1C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2683.9	Semi standard non polar	33892256
(??)-Clausenamide,1TBDMS,isomer #2	CN1C(=O)C(O[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)C1C(O)C1=CC=CC=C1	2693.6	Semi standard non polar	33892256
(??)-Clausenamide,2TBDMS,isomer #1	CN1C(=O)C(O[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)C1C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2877.9	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 - (±)-Clausenamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-2910000000-1f6143f1c873f05a4d06	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Clausenamide GC-MS (2 TMS) - 70eV, Positive	splash10-004i-1931000000-f4948ec4abdf560b2de7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Clausenamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Clausenamide 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 - (±)-Clausenamide 10V, Positive-QTOF	splash10-0002-0490000000-257fe7571432367b09b0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 20V, Positive-QTOF	splash10-0a4i-0910000000-6b6e68fcb22c2397ee69	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 40V, Positive-QTOF	splash10-0a4i-6900000000-d6550779df1caaec8a77	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 10V, Positive-QTOF	splash10-0002-0490000000-257fe7571432367b09b0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 20V, Positive-QTOF	splash10-0a4i-0910000000-6b6e68fcb22c2397ee69	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 40V, Positive-QTOF	splash10-0a4i-6900000000-d6550779df1caaec8a77	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 10V, Negative-QTOF	splash10-0002-1090000000-d34e1754ea0d68a7f626	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 20V, Negative-QTOF	splash10-002b-4290000000-7dcad8d3dc05f32b567b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 40V, Negative-QTOF	splash10-0573-9400000000-f0880a691c2a0454fc27	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 10V, Negative-QTOF	splash10-0002-1090000000-d34e1754ea0d68a7f626	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 20V, Negative-QTOF	splash10-002b-4290000000-7dcad8d3dc05f32b567b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 40V, Negative-QTOF	splash10-0573-9400000000-f0880a691c2a0454fc27	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 10V, Negative-QTOF	splash10-0002-0090000000-e348eb70757c0de7d3a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 20V, Negative-QTOF	splash10-002k-2790000000-e4e2f2085d7fad2571ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 40V, Negative-QTOF	splash10-05mo-2940000000-9b6c42fba6317f2cf285	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 10V, Positive-QTOF	splash10-0002-0090000000-9c534941bc73a95735e4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 20V, Positive-QTOF	splash10-0564-5490000000-185fba16cdbaac6b4b77	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Clausenamide 40V, Positive-QTOF	splash10-0006-9850000000-e59c39d9a72c246b29da	2021-09-23	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

FDB018044

KNApSAcK ID

Not Available

Chemspider ID

4475124

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315946

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1870171

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 (±)-Clausenamide (HMDB0038649)

MOL for HMDB0038649 ((±)-Clausenamide)

3D MOL for HMDB0038649 ((±)-Clausenamide)

3D SDF for HMDB0038649 ((±)-Clausenamide)

3D-SDF for HMDB0038649 ((±)-Clausenamide)

PDB for HMDB0038649 ((±)-Clausenamide)

3D PDB for HMDB0038649 ((±)-Clausenamide)

SMILES for HMDB0038649 ((±)-Clausenamide)

INCHI for HMDB0038649 ((±)-Clausenamide)

Structure for HMDB0038649 ((±)-Clausenamide)

3D Structure for HMDB0038649 ((±)-Clausenamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra