Showing metabocard for Tryptamine (MMDBc0000096)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:30:13 UTC
Update Date2024-10-09 21:22:24 UTC
Metabolite IDMMDBc0000096
Metabolite Identification
Common NameTryptamine
DescriptionTryptamine, also known as TrpN, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine (PMID: 30120222 ). Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000559d0464f0b8>


  Mrv1652309042000002D          

 12 13  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x0000559d0464f0b8>

HMDB0000303
     RDKit          3D
Tryptamine
 24 25  0  0  0  0  0  0  0  0999 V2000
    2.9094    0.2659   -0.6145 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    0.5611    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046   -0.6539    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.8578    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -1.7663   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -1.5473   -1.4165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -0.5189   -0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7315    0.0765   -1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    1.1296   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2923    1.5532    0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    0.9913    0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652   -0.0794    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    0.9571   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291   -0.7222   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    1.4571    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.7845    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611   -0.4813    2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2408   -1.5471    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -2.5146   -1.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -2.0749   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3317   -0.3197   -1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0955    1.6133   -0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.3792    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    1.3145    1.7637 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
Download

3D SDF for #<Metabolite:0x0000559d0464f0b8>


  Mrv1652309042000002D          

 12 13  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000096

> <DATABASE_NAME>
MIME

> <SMILES>
NCCC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

> <INCHI_KEY>
APJYDQYYACXCRM-UHFFFAOYSA-N

> <FORMULA>
C10H12N2

> <MOLECULAR_WEIGHT>
160.2157

> <EXACT_MASS>
160.100048394

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.336363890057264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1H-indol-3-yl)ethan-1-amine

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
1.48643745

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.170311785836876

> <JCHEM_PKA_STRONGEST_BASIC>
9.733973681017083

> <JCHEM_POLAR_SURFACE_AREA>
41.81

> <JCHEM_REFRACTIVITY>
50.37290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tryptamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x0000559d0464f0b8>

HMDB0000303
     RDKit          3D
Tryptamine
 24 25  0  0  0  0  0  0  0  0999 V2000
    2.9094    0.2659   -0.6145 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    0.5611    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046   -0.6539    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -0.8578    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -1.7663   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -1.5473   -1.4165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -0.5189   -0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7315    0.0765   -1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    1.1296   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2923    1.5532    0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    0.9913    0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652   -0.0794    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    0.9571   -1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291   -0.7222   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    1.4571    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.7845    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611   -0.4813    2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2408   -1.5471    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -2.5146   -1.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -2.0749   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3317   -0.3197   -1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0955    1.6133   -0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.3792    1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    1.3145    1.7637 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
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PDB for #<Metabolite:0x0000559d0464f0b8>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8669.1548664.625   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for #<Metabolite:0x0000559d0464f0b8>

COMPND    HMDB0000303
HETATM    1  N1  UNL     1       2.909   0.266  -0.614  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.409   0.561   0.707  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.605  -0.654   1.155  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.483  -0.858   0.184  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.341  -1.766  -0.828  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.842  -1.547  -1.417  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.491  -0.519  -0.824  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.731   0.076  -1.071  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.134   1.130  -0.281  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.292   1.553   0.722  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.070   0.991   0.988  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.665  -0.079   0.183  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.556   0.957  -1.002  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.229  -0.722  -0.711  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.742   1.457   0.595  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.159   0.784   1.461  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.161  -0.481   2.133  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.241  -1.547   1.138  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.088  -2.515  -1.070  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.242  -2.075  -2.220  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.332  -0.320  -1.877  1.00  0.00           H  
HETATM   22  H10 UNL     1      -4.096   1.613  -0.450  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.617   2.379   1.336  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.412   1.314   1.764  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5    5   12
CONECT    5    6   19
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   23
CONECT   11   12   12   24
END
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SMILES for #<Metabolite:0x0000559d0464f0b8>

NCCC1=CNC2=C1C=CC=C2
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INCHI for #<Metabolite:0x0000559d0464f0b8>

InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
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Synonyms
ValueSource
1H-Indole-3-ethanamineChEBI
2-(1H-indol-3-yl)ETHANAMINEChEBI
2-(3-Indolyl)ethylamineChEBI
3-(2-Aminoethyl)indoleChEBI
(3-Indolyl)ethylamineHMDB
2-(1H-indol-3-yl)EthylamineHMDB
2-indol-3-yl-AethylaminHMDB
2-indol-3-yl-EthylamineHMDB
3-(2-Aminoethyl)-1H-indoleHMDB
3-IndoleethanamineHMDB
3-IndoleethylamineHMDB
TryptaminHMDB
2-(1H-indol-3-yl)Ethan-1-amineHMDB
beta-(3-Indolyl)ethylamineHMDB
Β-(3-indolyl)ethylamineHMDB
TRPNHMDB
TryptamineHMDB
Molecular FormulaC10H12N2
Average Mass160.2157
Monoisotopic Mass160.100048394
IUPAC Name2-(1H-indol-3-yl)ethan-1-amine
Traditional Nametryptamine
CAS Registry Number61-54-1
SMILES
NCCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
InChI KeyAPJYDQYYACXCRM-UHFFFAOYSA-N