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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:28:07 UTC

Update Date

2022-03-07 02:54:09 UTC

HMDB ID

HMDB0034591

Secondary Accession Numbers

HMDB34591

Metabolite Identification

Common Name

Lansamide 3

Description

Lansamide 3 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. Lansamide 3 has been detected, but not quantified in, fruits. This could make lansamide 3 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lansamide 3.

Structure

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

HMDB0034591
     RDKit          3D
Lansamide 3
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.6014    4.0503    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    2.8816   -0.0854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046    2.9882   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1778    4.1196   -0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840    1.7944    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068    1.9884   -0.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    0.5300   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201   -0.6102    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8805   -0.8817    1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6669   -1.9793    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -2.7717    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227   -2.5240   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.4257   -0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5888    0.5112    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028   -0.7439   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8319   -1.4795    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -2.6675    0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6726   -3.1284   -0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456   -2.3994   -1.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600   -1.2084   -1.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563    1.6301   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    1.4693   -0.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8568    4.5934   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0001    4.7540    0.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4937    3.8007    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408    1.7080    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4118    2.3227    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    0.6100   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -0.2807    2.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617   -2.1781    2.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810   -3.6311    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151   -3.1470   -1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753   -1.2753   -2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740    0.7033    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -1.1567    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -3.2343    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996   -4.0481   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -2.7749   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0576   -0.6606   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    1.4907   -1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    2.2605   -0.2321 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 21  2  1  0
 13  8  1  0
 20 15  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
 16 35  1  0
 17 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 05061307562D          

 22 24  0  0  0  0            999 V2000
   -1.4289    3.3000    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
    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
   -2.1434    1.2375    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
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034591

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
FTFQYXRXXIHIHC-UHFFFAOYSA-N

> <FORMULA>
C18H19NO3

> <MOLECULAR_WEIGHT>
297.3484

> <EXACT_MASS>
297.136493479

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.566353266758682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6-dihydroxy-1-methyl-4,5-diphenylpiperidin-2-one

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.7365484350000002

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.311320935985247

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.637500501988956

> <JCHEM_PKA_STRONGEST_BASIC>
-3.613543896430481

> <JCHEM_POLAR_SURFACE_AREA>
60.77

> <JCHEM_REFRACTIVITY>
83.4661

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6-dihydroxy-1-methyl-4,5-diphenylpiperidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034591
     RDKit          3D
Lansamide 3
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.6014    4.0503    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    2.8816   -0.0854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046    2.9882   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1778    4.1196   -0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840    1.7944    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068    1.9884   -0.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    0.5300   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201   -0.6102    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8805   -0.8817    1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6669   -1.9793    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -2.7717    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227   -2.5240   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.4257   -0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5888    0.5112    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028   -0.7439   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8319   -1.4795    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -2.6675    0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6726   -3.1284   -0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456   -2.3994   -1.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600   -1.2084   -1.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563    1.6301   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    1.4693   -0.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8568    4.5934   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0001    4.7540    0.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4937    3.8007    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408    1.7080    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4118    2.3227    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    0.6100   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -0.2807    2.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617   -2.1781    2.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810   -3.6311    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151   -3.1470   -1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753   -1.2753   -2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740    0.7033    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -1.1567    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -3.2343    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996   -4.0481   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -2.7749   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0576   -0.6606   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    1.4907   -1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    2.2605   -0.2321 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 21  2  1  0
 13  8  1  0
 20 15  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
 16 35  1  0
 17 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                                 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      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -2.667   4.620   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.335   4.620   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   12                                                       
CONECT    9    5   12                                                       
CONECT   10    6   13                                                       
CONECT   11    7   13                                                       
CONECT   12    8    9   14                                                  
CONECT   13   10   11   15                                                  
CONECT   14   12   15   16                                                  
CONECT   15   13   14   17                                                  
CONECT   16   14   18   20                                                  
CONECT   17   15   19   21                                                  
CONECT   18   16   19   22                                                  
CONECT   19    1   17   18                                                  
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0034591
HETATM    1  C1  UNL     1       1.601   4.050   0.266  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.825   2.882  -0.085  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.605   2.988  -0.015  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.178   4.120  -0.047  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.484   1.794   0.099  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.707   1.988  -0.562  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.803   0.530  -0.361  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.620  -0.610   0.022  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.881  -0.882   1.341  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.667  -1.979   1.716  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.167  -2.772   0.733  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.923  -2.524  -0.600  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.137  -1.426  -0.952  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.589   0.511   0.221  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.303  -0.744  -0.085  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.832  -1.479   0.948  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.518  -2.667   0.765  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.673  -3.128  -0.521  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.146  -2.399  -1.574  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.460  -1.208  -1.372  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.356   1.630  -0.497  1.00  0.00           C  
HETATM   22  O3  UNL     1       2.698   1.469  -0.374  1.00  0.00           O  
HETATM   23  H1  UNL     1       1.857   4.593  -0.668  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.000   4.754   0.879  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.494   3.801   0.880  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.741   1.708   1.191  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.412   2.323   0.073  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.688   0.610  -1.462  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.505  -0.281   2.162  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.862  -2.178   2.757  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.781  -3.631   0.986  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.315  -3.147  -1.393  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.975  -1.275  -2.010  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.574   0.703   1.302  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.737  -1.157   1.993  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.928  -3.234   1.593  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.200  -4.048  -0.704  1.00  0.00           H  
HETATM   38  H16 UNL     1       2.274  -2.775  -2.595  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.058  -0.661  -2.232  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.092   1.491  -1.585  1.00  0.00           H  
HETATM   41  H19 UNL     1       3.237   2.260  -0.232  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   21
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   21   34
CONECT   15   16   16   20
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   20   39
CONECT   21   22   40
CONECT   22   41
END

HMDB0034591
     RDKit          3D
Lansamide 3
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.6014    4.0503    0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    2.8816   -0.0854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046    2.9882   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1778    4.1196   -0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840    1.7944    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068    1.9884   -0.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    0.5300   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201   -0.6102    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8805   -0.8817    1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6669   -1.9793    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -2.7717    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227   -2.5240   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -1.4257   -0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5888    0.5112    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028   -0.7439   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8319   -1.4795    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -2.6675    0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6726   -3.1284   -0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456   -2.3994   -1.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4600   -1.2084   -1.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563    1.6301   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    1.4693   -0.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8568    4.5934   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0001    4.7540    0.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4937    3.8007    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408    1.7080    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4118    2.3227    0.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6883    0.6100   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -0.2807    2.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617   -2.1781    2.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810   -3.6311    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151   -3.1470   -1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753   -1.2753   -2.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740    0.7033    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -1.1567    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -3.2343    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1996   -4.0481   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -2.7749   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0576   -0.6606   -2.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    1.4907   -1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    2.2605   -0.2321 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 21  2  1  0
 13  8  1  0
 20 15  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
 16 35  1  0
 17 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

Value	Source
3,6-Dihydroxy-1-methyl-4,5-diphenyl-2-piperidinone	HMDB
Lansimide 3?	HMDB

Chemical Formula

C₁₈H₁₉NO₃

Average Molecular Weight

297.3484

Monoisotopic Molecular Weight

297.136493479

IUPAC Name

3,6-dihydroxy-1-methyl-4,5-diphenylpiperidin-2-one

Traditional Name

3,6-dihydroxy-1-methyl-4,5-diphenylpiperidin-2-one

CAS Registry Number

211504-98-2

SMILES

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

InChI Identifier

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

InChI Key

FTFQYXRXXIHIHC-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
Phenylpiperidine
Delta-lactam
Piperidinone
Monocyclic benzene moiety
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Alkanolamine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
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: HMDB0034591)
Cytoplasm (HMDB: HMDB0034591)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034591)

Source

Exogenous

Food

Food (HMDB: HMDB0034591)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034591)

Not Available

Nutrient (HMDB: HMDB0034591)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	236 - 237 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.48 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.74	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.64	ChemAxon
pKa (Strongest Basic)	-3.6	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	2	ChemAxon
Refractivity	83.47 m³·mol⁻¹	ChemAxon
Polarizability	31.57 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]+	169.189	31661259
DarkChem	[M-H]-	165.971	31661259
DeepCCS	[M+H]+	167.835	30932474
DeepCCS	[M-H]-	165.477	30932474
DeepCCS	[M-2H]-	198.443	30932474
DeepCCS	[M+Na]+	173.929	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	175.0	32859911
AllCCS	[M+Na]+	175.9	32859911
AllCCS	[M-H]-	174.9	32859911
AllCCS	[M+Na-2H]-	174.7	32859911
AllCCS	[M+HCOO]-	174.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lansamide 3	CN1C(O)C(C(C(O)C1=O)C1=CC=CC=C1)C1=CC=CC=C1	3914.5	Standard polar	33892256
Lansamide 3	CN1C(O)C(C(C(O)C1=O)C1=CC=CC=C1)C1=CC=CC=C1	2577.4	Standard non polar	33892256
Lansamide 3	CN1C(O)C(C(C(O)C1=O)C1=CC=CC=C1)C1=CC=CC=C1	2705.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lansamide 3,1TMS,isomer #1	CN1C(=O)C(O)C(C2=CC=CC=C2)C(C2=CC=CC=C2)C1O[Si](C)(C)C	2475.4	Semi standard non polar	33892256
Lansamide 3,1TMS,isomer #2	CN1C(=O)C(O[Si](C)(C)C)C(C2=CC=CC=C2)C(C2=CC=CC=C2)C1O	2478.0	Semi standard non polar	33892256
Lansamide 3,2TMS,isomer #1	CN1C(=O)C(O[Si](C)(C)C)C(C2=CC=CC=C2)C(C2=CC=CC=C2)C1O[Si](C)(C)C	2526.6	Semi standard non polar	33892256
Lansamide 3,1TBDMS,isomer #1	CN1C(=O)C(O)C(C2=CC=CC=C2)C(C2=CC=CC=C2)C1O[Si](C)(C)C(C)(C)C	2738.0	Semi standard non polar	33892256
Lansamide 3,1TBDMS,isomer #2	CN1C(=O)C(O[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)C(C2=CC=CC=C2)C1O	2744.0	Semi standard non polar	33892256
Lansamide 3,2TBDMS,isomer #1	CN1C(=O)C(O[Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)C(C2=CC=CC=C2)C1O[Si](C)(C)C(C)(C)C	2968.4	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 - Lansamide 3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-00o3-3920000000-dab9a1d7aa4d97a0f272	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lansamide 3 GC-MS (2 TMS) - 70eV, Positive	splash10-00pl-2952100000-cd04b226285bdf6e22b7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lansamide 3 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 - Lansamide 3 10V, Positive-QTOF	splash10-0002-0090000000-b026a064e2b5af47daaf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 20V, Positive-QTOF	splash10-0005-3190000000-7eeb89a9780553113a65	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 40V, Positive-QTOF	splash10-002f-9410000000-282abb19ab8dce2f8b01	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 10V, Negative-QTOF	splash10-0002-0090000000-1000ecfbdcfa49bafd3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 20V, Negative-QTOF	splash10-0002-2590000000-383ad0e15e4c6b943999	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 40V, Negative-QTOF	splash10-0a4i-9210000000-5fdd834e91bef0a481e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 10V, Positive-QTOF	splash10-0002-0090000000-8170e81c932b27780e3c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 20V, Positive-QTOF	splash10-0002-1390000000-e4a9f1e411c8aedd15ee	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 40V, Positive-QTOF	splash10-0006-6900000000-10ec26408a73daae0fc9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 10V, Negative-QTOF	splash10-0002-0090000000-f0a7b42101b1968126a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 20V, Negative-QTOF	splash10-0002-2390000000-2484cbd4e3801732394e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 3 40V, Negative-QTOF	splash10-004i-4930000000-cddd9624af914dc66323	2021-09-24	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

FDB013107

KNApSAcK ID

Not Available

Chemspider ID

8860764

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10685418

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Enzymes

Enzyme Details

1. Alcohol dehydrogenase class 4 mu/sigma chain

General function:: Involved in zinc ion binding
Specific function:: Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:: ADH7
Uniprot ID:: P40394
Molecular weight:: 41480.985

Reactions

Lansamide 3 → 3-hydroxy-1-methyl-4,5-diphenylpiperidine-2,6-dione	details

Showing metabocard for Lansamide 3 (HMDB0034591)

MOL for HMDB0034591 (Lansamide 3)

3D MOL for HMDB0034591 (Lansamide 3)

3D SDF for HMDB0034591 (Lansamide 3)

3D-SDF for HMDB0034591 (Lansamide 3)

PDB for HMDB0034591 (Lansamide 3)

3D PDB for HMDB0034591 (Lansamide 3)

SMILES for HMDB0034591 (Lansamide 3)

INCHI for HMDB0034591 (Lansamide 3)

Structure for HMDB0034591 (Lansamide 3)

3D Structure for HMDB0034591 (Lansamide 3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions