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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-07-22 15:42:19 UTC

Update Date

2021-09-14 15:46:16 UTC

HMDB ID

HMDB0061115

Secondary Accession Numbers

HMDB61115

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>
HMDB0061115

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₄H₁₈N₂O₂

Average Molecular Weight

246.3049

Monoisotopic Molecular Weight

246.13682783

IUPAC Name

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

Traditional Name

hypaphorine

CAS Registry Number

487-58-1

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Placenta (HMDB: HMDB0061115)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)
Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0061115)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	186.278	30932474
DeepCCS	[M+Na]+	161.843	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.6	32859911
AllCCS	[M+NH4]+	159.5	32859911
AllCCS	[M+Na]+	160.4	32859911
AllCCS	[M-H]-	166.5	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	167.6	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.	3.0 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0229 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1340.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	251.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	366.9 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	320.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	503.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1128.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	342.0 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	1415.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	273.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	389.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	321.9 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	37.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lenticin	C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O	2977.1	Standard polar	33892256
Lenticin	C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O	1718.8	Standard non polar	33892256
Lenticin	C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O	2232.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lenticin,1TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]	2159.5	Semi standard non polar	33892256
Lenticin,1TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]	2120.1	Standard non polar	33892256
Lenticin,1TMS,isomer #1	C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]	2583.3	Standard polar	33892256
Lenticin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C21	2358.7	Semi standard non polar	33892256
Lenticin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C21	2336.6	Standard non polar	33892256
Lenticin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C21	2652.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lenticin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-5890000000-7a32ae6df95ecbe4b4d5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lenticin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lenticin 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 - Lenticin 10V, Positive-QTOF	splash10-0002-0290000000-c42f376f71f6e3725267	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 20V, Positive-QTOF	splash10-0f7k-0390000000-f1efb195c18ebf5ebaaf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 40V, Positive-QTOF	splash10-0f89-0900000000-d8339c908340d1176dc0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 10V, Negative-QTOF	splash10-0002-0290000000-4b553f8b8e9e0606e117	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 20V, Negative-QTOF	splash10-000b-0890000000-d5d7c7edd0b4db429160	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 40V, Negative-QTOF	splash10-014i-0900000000-8c56dbdaac5dc7a92a2e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 10V, Negative-QTOF	splash10-0002-0090000000-fdb1f9281332d5149644	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 20V, Negative-QTOF	splash10-014i-0910000000-a89d64e0d176721c5891	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 40V, Negative-QTOF	splash10-016r-0900000000-b4ddbcb87a2999e94631	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 10V, Positive-QTOF	splash10-0udi-0190000000-ec4a6e5db2f844802dc9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 20V, Positive-QTOF	splash10-001l-0910000000-0b46677e1ee9ee59d663	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lenticin 40V, Positive-QTOF	splash10-0006-6900000000-c7a3ff32cff4a5522e4d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

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

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

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 (HMDB0061115)

MOL for HMDB0061115 (Lenticin)

3D MOL for HMDB0061115 (Lenticin)

3D SDF for HMDB0061115 (Lenticin)

3D-SDF for HMDB0061115 (Lenticin)

PDB for HMDB0061115 (Lenticin)

3D PDB for HMDB0061115 (Lenticin)

SMILES for HMDB0061115 (Lenticin)

INCHI for HMDB0061115 (Lenticin)

Structure for HMDB0061115 (Lenticin)

3D Structure for HMDB0061115 (Lenticin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra