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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:28:11 UTC

Update Date

2022-03-07 02:54:09 UTC

HMDB ID

HMDB0034592

Secondary Accession Numbers

HMDB34592

Metabolite Identification

Common Name

Lansamide 4

Description

Lansamide 4 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 4 has been detected, but not quantified in, fruits. This could make lansamide 4 a potential biomarker for the consumption of these foods. Lansamide 4 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Lansamide 4.

Structure

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

HMDB0034592
     RDKit          3D
Lansamide 4
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.5547    1.3407    2.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6860    1.4818    1.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3452    1.2861    0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171    0.3003   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -1.0977   -0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -1.9014   -1.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8850   -3.2281   -1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341   -3.7737    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0848   -3.0116    1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7842   -1.6874    0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905    0.6103   -0.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7501   -0.2661   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152   -0.4066    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2362   -1.2707    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8413   -2.0475    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064   -1.9386   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916   -1.0716   -1.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    2.0305   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929    2.4708   -1.2053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539    2.9811   -0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    4.0788   -1.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3379    2.5865   -0.2964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5211    3.3823   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626    1.4910    3.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    0.3516    2.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522    2.1233    2.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194    1.0441    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177    0.5381   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -1.5195   -2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3210   -3.8756   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -4.8208    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816   -3.4373    2.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593   -1.1286    1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7504    0.6694   -2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7341    0.2054    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5437   -1.3190    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400   -2.7297    0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764   -2.5468   -1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973   -1.0365   -2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309    2.0711    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    2.2941   -2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384    4.4450   -0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8389    3.2919   -1.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2890    3.0406    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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
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 13 14  1  0
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 22  3  1  0
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 17 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
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  6 29  1  0
  7 30  1  0
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 13 35  1  0
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 16 38  1  0
 17 39  1  0
 18 40  1  0
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 23 44  1  0
M  END


  Mrv0541 05061307562D          

 23 25  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
    0.0000    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
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 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
   -2.8579    2.4750    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
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
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 19 16  1  0  0  0  0
 20  1  1  0  0  0  0
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 21 17  1  0  0  0  0
 22 18  2  0  0  0  0
 23  2  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034592

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO3/c1-20-18(22)17(21)15(13-9-5-3-6-10-13)16(19(20)23-2)14-11-7-4-8-12-14/h3-12,15-17,19,21H,1-2H3

> <INCHI_KEY>
HGOXSQCBJLZRJO-UHFFFAOYSA-N

> <FORMULA>
C19H21NO3

> <MOLECULAR_WEIGHT>
311.3749

> <EXACT_MASS>
311.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.585612182259354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.3796749386666667

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.80261613841817

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7599346958408555

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
88.21730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034592
     RDKit          3D
Lansamide 4
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.5547    1.3407    2.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6860    1.4818    1.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3452    1.2861    0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171    0.3003   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -1.0977   -0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -1.9014   -1.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8850   -3.2281   -1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341   -3.7737    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0848   -3.0116    1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7842   -1.6874    0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905    0.6103   -0.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7501   -0.2661   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152   -0.4066    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2362   -1.2707    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8413   -2.0475    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064   -1.9386   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916   -1.0716   -1.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    2.0305   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929    2.4708   -1.2053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539    2.9811   -0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    4.0788   -1.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3379    2.5865   -0.2964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5211    3.3823   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626    1.4910    3.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    0.3516    2.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522    2.1233    2.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194    1.0441    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177    0.5381   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -1.5195   -2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3210   -3.8756   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -4.8208    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816   -3.4373    2.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593   -1.1286    1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7504    0.6694   -2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7341    0.2054    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5437   -1.3190    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400   -2.7297    0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764   -2.5468   -1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973   -1.0365   -2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309    2.0711    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    2.2941   -2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384    4.4450   -0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8389    3.2919   -1.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2890    3.0406    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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 22  1  0
 22 23  1  0
 22  3  1  0
 10  5  1  0
 17 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   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      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   2.310   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  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -2.667   4.620   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -5.335   1.540   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
HETATM   23  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   23                                                            
CONECT    3    5    6                                                       
CONECT    4    7    8                                                       
CONECT    5    3    9                                                       
CONECT    6    3   10                                                       
CONECT    7    4   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   13                                                       
CONECT   11    7   14                                                       
CONECT   12    8   14                                                       
CONECT   13    9   10   15                                                  
CONECT   14   11   12   16                                                  
CONECT   15   13   16   17                                                  
CONECT   16   14   15   19                                                  
CONECT   17   15   18   21                                                  
CONECT   18   17   20   22                                                  
CONECT   19   16   20   23                                                  
CONECT   20    1   18   19                                                  
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23    2   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0034592
HETATM    1  C1  UNL     1      -1.555   1.341   2.643  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.686   1.482   1.569  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.345   1.286   0.401  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.717   0.300  -0.566  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.014  -1.098  -0.264  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.570  -1.901  -1.234  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.885  -3.228  -1.017  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.634  -3.774   0.223  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.085  -3.012   1.212  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.784  -1.687   0.953  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.691   0.610  -0.940  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.750  -0.266  -0.503  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.215  -0.407   0.785  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.236  -1.271   1.143  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.841  -2.047   0.179  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.406  -1.939  -1.126  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.392  -1.072  -1.446  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.058   2.030  -0.508  1.00  0.00           C  
HETATM   19  O2  UNL     1       2.193   2.471  -1.205  1.00  0.00           O  
HETATM   20  C18 UNL     1      -0.054   2.981  -0.761  1.00  0.00           C  
HETATM   21  O3  UNL     1       0.099   4.079  -1.350  1.00  0.00           O  
HETATM   22  N1  UNL     1      -1.338   2.587  -0.296  1.00  0.00           N  
HETATM   23  C19 UNL     1      -2.521   3.382  -0.488  1.00  0.00           C  
HETATM   24  H1  UNL     1      -1.063   1.491   3.616  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.054   0.352   2.600  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.352   2.123   2.494  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.419   1.044   0.503  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.318   0.538  -1.514  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.791  -1.520  -2.241  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.321  -3.876  -1.764  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.860  -4.821   0.465  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.882  -3.437   2.202  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.359  -1.129   1.767  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.750   0.669  -2.074  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.734   0.205   1.522  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.544  -1.319   2.193  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.640  -2.730   0.431  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.876  -2.547  -1.897  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.097  -1.036  -2.500  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.331   2.071   0.559  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.120   2.294  -2.176  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.238   4.445  -0.297  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.839   3.292  -1.528  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.289   3.041   0.238  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4   22   27
CONECT    4    5   11   28
CONECT    5    6    6   10
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   33
CONECT   11   12   18   34
CONECT   12   13   13   17
CONECT   13   14   35
CONECT   14   15   15   36
CONECT   15   16   37
CONECT   16   17   17   38
CONECT   17   39
CONECT   18   19   20   40
CONECT   19   41
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   42   43   44
END

HMDB0034592
     RDKit          3D
Lansamide 4
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.5547    1.3407    2.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6860    1.4818    1.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3452    1.2861    0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171    0.3003   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -1.0977   -0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -1.9014   -1.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8850   -3.2281   -1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341   -3.7737    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0848   -3.0116    1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7842   -1.6874    0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905    0.6103   -0.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7501   -0.2661   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152   -0.4066    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2362   -1.2707    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8413   -2.0475    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064   -1.9386   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916   -1.0716   -1.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    2.0305   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929    2.4708   -1.2053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539    2.9811   -0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    4.0788   -1.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3379    2.5865   -0.2964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5211    3.3823   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626    1.4910    3.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    0.3516    2.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522    2.1233    2.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194    1.0441    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177    0.5381   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -1.5195   -2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3210   -3.8756   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -4.8208    0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816   -3.4373    2.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593   -1.1286    1.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7504    0.6694   -2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7341    0.2054    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5437   -1.3190    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400   -2.7297    0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764   -2.5468   -1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973   -1.0365   -2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309    2.0711    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    2.2941   -2.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384    4.4450   -0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8389    3.2919   -1.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2890    3.0406    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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 22  1  0
 22 23  1  0
 22  3  1  0
 10  5  1  0
 17 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-6-methoxy-1-methyl-4,5-diphenyl-2-piperidinon	ChEBI
3-Hydroxy-6-methoxy-1-methyl-4,5-diphenyl-2-piperidinone	HMDB
Lansimide 4	HMDB

Chemical Formula

C₁₉H₂₁NO₃

Average Molecular Weight

311.3749

Monoisotopic Molecular Weight

311.152143543

IUPAC Name

3-hydroxy-6-methoxy-1-methyl-4,5-diphenylpiperidin-2-one

Traditional Name

3-hydroxy-6-methoxy-1-methyl-4,5-diphenylpiperidin-2-one

CAS Registry Number

211505-00-9

SMILES

COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H21NO3/c1-20-18(22)17(21)15(13-9-5-3-6-10-13)16(19(20)23-2)14-11-7-4-8-12-14/h3-12,15-17,19,21H,1-2H3

InChI Key

HGOXSQCBJLZRJO-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
Benzenoid
Piperidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen 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: HMDB0034592)
Cytoplasm (HMDB: HMDB0034592)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034592)

Source

Exogenous

Exogenous (HMDB: HMDB0034592)

Food

Food (HMDB: HMDB0034592)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034592)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034592)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	187 - 188 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	2.04	ALOGPS
logP	2.38	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.22 m³·mol⁻¹	ChemAxon
Polarizability	33.59 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]+	171.722	31661259
DarkChem	[M-H]-	171.062	31661259
DeepCCS	[M+H]+	173.385	30932474
DeepCCS	[M-H]-	171.027	30932474
DeepCCS	[M-2H]-	204.916	30932474
DeepCCS	[M+Na]+	180.328	30932474
AllCCS	[M+H]+	175.0	32859911
AllCCS	[M+H-H2O]+	171.5	32859911
AllCCS	[M+NH4]+	178.3	32859911
AllCCS	[M+Na]+	179.3	32859911
AllCCS	[M-H]-	179.8	32859911
AllCCS	[M+Na-2H]-	179.7	32859911
AllCCS	[M+HCOO]-	179.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.06 minutes	32390414
Predicted by Siyang on May 30, 2022	14.8779 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2568.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	363.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	200.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	147.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	618.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	687.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1434.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	533.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1535.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	414.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	243.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	153.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lansamide 4	COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C1	3708.4	Standard polar	33892256
Lansamide 4	COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C1	2522.0	Standard non polar	33892256
Lansamide 4	COC1C(C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C1	2521.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lansamide 4,1TMS,isomer #1	COC1C(C2=CC=CC=C2)C(C2=CC=CC=C2)C(O[Si](C)(C)C)C(=O)N1C	2434.3	Semi standard non polar	33892256
Lansamide 4,1TBDMS,isomer #1	COC1C(C2=CC=CC=C2)C(C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)C(=O)N1C	2673.3	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 4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-1930000000-0cff559141d8524d92a9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lansamide 4 GC-MS (1 TMS) - 70eV, Positive	splash10-0036-3951000000-3b0aae81bc235033ace2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lansamide 4 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 4 10V, Positive-QTOF	splash10-03di-0039000000-983af54750d2fcf9c95e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 20V, Positive-QTOF	splash10-03dl-4195000000-c38b92a5091845a79d78	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 40V, Positive-QTOF	splash10-0006-9310000000-af961ee1346a36f0c438	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 10V, Negative-QTOF	splash10-03di-0009000000-ff5ecec3f5761d831960	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 20V, Negative-QTOF	splash10-03di-2896000000-456f8e4c4de50ea8600a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 40V, Negative-QTOF	splash10-0a4i-9210000000-270a81024d3cf12d2d3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 10V, Negative-QTOF	splash10-03di-0009000000-9bf675b2e28db05b0d3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 20V, Negative-QTOF	splash10-03di-0169000000-8d2ea231d305ff6c5b28	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 40V, Negative-QTOF	splash10-004i-3932000000-a450800a70d9514c2d6d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 10V, Positive-QTOF	splash10-03di-0039000000-5f9b875c4e3d4c439a92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 20V, Positive-QTOF	splash10-03e9-0395000000-db8e75418eb8c7e984a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansamide 4 40V, Positive-QTOF	splash10-0f8c-3920000000-be8953720c9fc6f42b02	2021-09-22	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

FDB013108

KNApSAcK ID

Not Available

Chemspider ID

8694499

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10519101

PDB ID

Not Available

ChEBI ID

141548

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Lansamide 4 (HMDB0034592)

MOL for HMDB0034592 (Lansamide 4)

3D MOL for HMDB0034592 (Lansamide 4)

3D SDF for HMDB0034592 (Lansamide 4)

3D-SDF for HMDB0034592 (Lansamide 4)

PDB for HMDB0034592 (Lansamide 4)

3D PDB for HMDB0034592 (Lansamide 4)

SMILES for HMDB0034592 (Lansamide 4)

INCHI for HMDB0034592 (Lansamide 4)

Structure for HMDB0034592 (Lansamide 4)

3D Structure for HMDB0034592 (Lansamide 4)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra