MiMeDB: Showing metabocard for Lenticin (MMDBc0000486)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:52 UTC

Update Date

2022-08-31 06:07:01 UTC

Metabolite ID

MMDBc0000486

Metabolite Identification

Common Name

Lenticin

Description

Lenticin or hypaphorine is a compound found in lentil extracts. It can also be detected in blood after an individual has consumed lentils and may therefore serve as a food biomarker. Lenticin is an indole alkaloid that is essentially an N-methylated form of tryptophan. It is known to be a sleep-inducing compound (PMID: 18571406 ). In plants it is an agonist of the plant hormone indole acetic acid.

Structure

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

HMDB0061115
     RDKit          3D
Lenticin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.1000   -1.0617    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390    0.2810    0.2225 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6582    1.0023    1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5640    1.0207   -0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    0.4067   -0.3511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2295    0.0718    0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    0.2517   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    1.0744   -1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5727    1.0184   -1.5192 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874    0.1708   -0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5088   -0.2306   -0.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.1177    0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299   -1.5924    1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -1.2280    1.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766   -0.3224    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1233   -0.4825   -1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -1.5444   -1.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343   -0.1326   -2.7343 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4319   -1.5830    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343   -1.5954   -0.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.9625    0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976    1.9448    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3112    0.4150    2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174    1.2742    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6092    0.9747   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038    2.0806   -0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    0.6706   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749    1.4889   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -1.0025    0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607    0.6727    1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628    1.6794   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    1.5368   -2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2323    0.1557   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -1.4167    0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3914   -2.3051    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0035   -1.6137    1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
M  CHG  2   2   1  18  -1
M  END


  Mrv1652309121709232D          

 18 19  0  0  1  0            999 V2000
   -0.4331   -3.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.6065   -3.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628   -2.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  7 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  CHG  2   2   1  18  -1
M  END
> <DATABASE_ID>
MMDBc0000486

> <DATABASE_NAME>
MIME

> <SMILES>
C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1

> <INCHI_KEY>
AOHCBEAZXHZMOR-ZDUSSCGKSA-N

> <FORMULA>
C14H18N2O2

> <MOLECULAR_WEIGHT>
246.3049

> <EXACT_MASS>
246.13682783

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.59984748350832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-2.1703312394717456

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.093293216964362

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.604075853879379

> <JCHEM_POLAR_SURFACE_AREA>
55.92

> <JCHEM_REFRACTIVITY>
93.0228

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hypaphorine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061115
     RDKit          3D
Lenticin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.1000   -1.0617    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390    0.2810    0.2225 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6582    1.0023    1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5640    1.0207   -0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    0.4067   -0.3511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2295    0.0718    0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    0.2517   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    1.0744   -1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5727    1.0184   -1.5192 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874    0.1708   -0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5088   -0.2306   -0.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.1177    0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299   -1.5924    1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -1.2280    1.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766   -0.3224    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1233   -0.4825   -1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -1.5444   -1.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343   -0.1326   -2.7343 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4319   -1.5830    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343   -1.5954   -0.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.9625    0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976    1.9448    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3112    0.4150    2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174    1.2742    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6092    0.9747   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038    2.0806   -0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    0.6706   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749    1.4889   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -1.0025    0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607    0.6727    1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628    1.6794   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    1.5368   -2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2323    0.1557   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -1.4167    0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3914   -2.3051    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0035   -1.6137    1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
M  CHG  2   2   1  18  -1
M  END

HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  C   UNK     0      -0.808  -7.263   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       1.132  -6.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.797  -5.322   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.393  -3.509   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10    7                                                  
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0061115
HETATM    1  C1  UNL     1      -3.100  -1.062   0.419  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.639   0.281   0.223  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -2.658   1.002   1.491  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.564   1.021  -0.642  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.336   0.407  -0.351  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.229   0.072   0.651  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.060   0.252  -0.039  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.294   1.074  -1.139  1.00  0.00           C  
HETATM    9  N2  UNL     1       2.573   1.018  -1.519  1.00  0.00           N  
HETATM   10  C8  UNL     1       3.187   0.171  -0.687  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.509  -0.231  -0.659  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.944  -1.118   0.282  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.030  -1.592   1.191  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.716  -1.228   1.204  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.277  -0.322   0.241  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.123  -0.482  -1.504  1.00  0.00           C  
HETATM   17  O1  UNL     1      -0.489  -1.544  -1.378  1.00  0.00           O  
HETATM   18  O2  UNL     1      -1.634  -0.133  -2.734  1.00  0.00           O1-
HETATM   19  H1  UNL     1      -2.432  -1.583   1.123  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.234  -1.595  -0.520  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.112  -0.962   0.912  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.098   1.945   1.325  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.311   0.415   2.338  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.717   1.274   1.675  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.609   0.975  -0.263  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.204   2.081  -0.651  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.510   0.671  -1.687  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.175   1.489  -0.575  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.345  -1.002   0.918  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.261   0.673   1.557  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.563   1.679  -1.641  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.031   1.537  -2.324  1.00  0.00           H  
HETATM   33  H15 UNL     1       5.232   0.156  -1.388  1.00  0.00           H  
HETATM   34  H16 UNL     1       5.970  -1.417   0.289  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.391  -2.305   1.935  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.003  -1.614   1.930  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    5
CONECT    3   22   23   24
CONECT    4   25   26   27
CONECT    5    6   16   28
CONECT    6    7   29   30
CONECT    7    8    8   15
CONECT    8    9   31
CONECT    9   10   32
CONECT   10   11   11   15
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   35
CONECT   14   15   15   36
CONECT   16   17   17   18
END

HMDB0061115
     RDKit          3D
Lenticin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.1000   -1.0617    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390    0.2810    0.2225 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6582    1.0023    1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5640    1.0207   -0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    0.4067   -0.3511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2295    0.0718    0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    0.2517   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    1.0744   -1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5727    1.0184   -1.5192 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874    0.1708   -0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5088   -0.2306   -0.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.1177    0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299   -1.5924    1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165   -1.2280    1.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766   -0.3224    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1233   -0.4825   -1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -1.5444   -1.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343   -0.1326   -2.7343 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4319   -1.5830    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2343   -1.5954   -0.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1118   -0.9625    0.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976    1.9448    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3112    0.4150    2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174    1.2742    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6092    0.9747   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038    2.0806   -0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    0.6706   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749    1.4889   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -1.0025    0.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607    0.6727    1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628    1.6794   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    1.5368   -2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2323    0.1557   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -1.4167    0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3914   -2.3051    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0035   -1.6137    1.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
M  CHG  2   2   1  18  -1
M  END

Synonyms

Value	Source
(+)-Hypaphorine	ChEBI
Glyyunnanenine	ChEBI
L-Hypaphorine	ChEBI
L-Tryptophan betaine	ChEBI
N,N,N-Trimethyltryptophan betaine	ChEBI
Tryptophan betaine	ChEBI
Lenticin nitrate	HMDB
Hypaforin	HMDB
Lenticin	ChEBI

Molecular Formula

C₁₄H₁₈N₂O₂

Average Mass

246.3049

Monoisotopic Mass

246.13682783

IUPAC Name

(2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate

Traditional Name

hypaphorine

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O

InChI Identifier

InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1

InChI Key

AOHCBEAZXHZMOR-ZDUSSCGKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

3-alkylindole
L-alpha-amino acid
Indole
Indole or derivatives
Aralkylamine
Substituted pyrrole
Benzenoid
Tetraalkylammonium salt
Pyrrole
Heteroaromatic compound
Quaternary ammonium salt
Carboxylic acid salt
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Amine
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organic salt
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tryptamines (CHEBI:5832 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0026 g/L	ALOGPS
logP	-0.54	ALOGPS
logP	-2.2	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.02 m³·mol⁻¹	ChemAxon
Polarizability	26.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-5890000000-7a32ae6df95ecbe4b4d5	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0290000000-c42f376f71f6e3725267	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7k-0390000000-f1efb195c18ebf5ebaaf	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-0900000000-d8339c908340d1176dc0	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0290000000-4b553f8b8e9e0606e117	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000b-0890000000-d5d7c7edd0b4db429160	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-8c56dbdaac5dc7a92a2e	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-fdb1f9281332d5149644	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0910000000-a89d64e0d176721c5891	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-016r-0900000000-b4ddbcb87a2999e94631	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0190000000-ec4a6e5db2f844802dc9	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-0910000000-0b46677e1ee9ee59d663	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-6900000000-c7a3ff32cff4a5522e4d	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0061115

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001740

Chemspider ID

Not Available

KEGG Compound ID

C09213

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442106

PDB ID

Not Available

ChEBI ID

5832

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ozawa M, Honda K, Nakai I, Kishida A, Ohsaki A: Hypaphorine, an indole alkaloid from Erythrina velutina, induced sleep on normal mice. Bioorg Med Chem Lett. 2008 Jul 15;18(14):3992-4. doi: 10.1016/j.bmcl.2008.06.002. Epub 2008 Jun 6. [PubMed:18571406 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Lenticin (MMDBc0000486)

MOL for #<Metabolite:0x00007fe26a41c6d0>

3D MOL for #<Metabolite:0x00007fe26a41c6d0>

3D SDF for #<Metabolite:0x00007fe26a41c6d0>

3D-SDF for #<Metabolite:0x00007fe26a41c6d0>

PDB for #<Metabolite:0x00007fe26a41c6d0>

3D PDB for #<Metabolite:0x00007fe26a41c6d0>

SMILES for #<Metabolite:0x00007fe26a41c6d0>

INCHI for #<Metabolite:0x00007fe26a41c6d0>

Structure for #<Metabolite:0x00007fe26a41c6d0>

3D Structure for #<Metabolite:0x00007fe26a41c6d0>