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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:34:13 UTC

Update Date

2021-09-26 23:15:02 UTC

HMDB ID

HMDB0258257

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Serotonin O-sulfate

Description

[3-(2-aminoethyl)-1H-indol-5-yl]oxidanesulfonic acid belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. Based on a literature review very few articles have been published on [3-(2-aminoethyl)-1H-indol-5-yl]oxidanesulfonic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Serotonin o-sulfate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Serotonin O-sulfate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0258257
     RDKit          3D
Serotonin O-sulfate
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.0628    0.7995   -0.9219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924    1.3421    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0006    1.2419    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.1485    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.3292    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949   -2.3121    0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0323   -1.8188    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2080   -2.4148    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3477   -1.6277    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390   -0.2581    0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3911    0.4938    0.5805 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    1.0917   -0.7550 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.7077    2.4638   -1.0576 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.1844   -1.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8718    1.2416   -0.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018    0.3380    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493   -0.4337    0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518    1.4978   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    0.2577   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7531    2.4205    0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224    0.8889    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614    1.6858    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5265    1.7880   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2885   -1.3897    0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296   -3.3269    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2952   -3.4902    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012   -2.1494    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8426    1.5543    0.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930    1.4095    0.5044 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  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
 10 16  1  0
 16 17  2  0
 17  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 15 28  1  0
 16 29  1  0
M  END

  Mrv0541 04121517372D          

 17 18  0  0  0  0            999 V2000
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  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
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937   -1.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3687   -0.3960    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4 17  1  0  0  0  0
  7 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258257

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCC1=CNC2=CC=C(OS(O)(=O)=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O4S/c11-4-3-7-6-12-10-2-1-8(5-9(7)10)16-17(13,14)15/h1-2,5-6,12H,3-4,11H2,(H,13,14,15)

> <INCHI_KEY>
JFWYSGGSCOOBGK-UHFFFAOYSA-N

> <FORMULA>
C10H12N2O4S

> <MOLECULAR_WEIGHT>
256.28

> <EXACT_MASS>
256.051778048

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
24.583599358725394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[3-(2-aminoethyl)-1H-indol-5-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.91

> <JCHEM_LOGP>
-0.3019588840654538

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.210662661552373

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.6599967979328207

> <JCHEM_PKA_STRONGEST_BASIC>
9.742028868819078

> <JCHEM_POLAR_SURFACE_AREA>
105.41000000000001

> <JCHEM_REFRACTIVITY>
62.34560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3-(2-aminoethyl)-1H-indol-5-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258257
     RDKit          3D
Serotonin O-sulfate
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.0628    0.7995   -0.9219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924    1.3421    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0006    1.2419    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.1485    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.3292    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949   -2.3121    0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0323   -1.8188    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2080   -2.4148    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3477   -1.6277    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390   -0.2581    0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3911    0.4938    0.5805 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    1.0917   -0.7550 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.7077    2.4638   -1.0576 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.1844   -1.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8718    1.2416   -0.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018    0.3380    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493   -0.4337    0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518    1.4978   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    0.2577   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7531    2.4205    0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224    0.8889    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614    1.6858    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5265    1.7880   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2885   -1.3897    0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296   -3.3269    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2952   -3.4902    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012   -2.1494    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8426    1.5543    0.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930    1.4095    0.5044 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  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
 10 16  1  0
 16 17  2  0
 17  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 15 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0       8.925  -2.073   0.000  0.00  0.00           S+0
HETATM   13  O   UNK     0      10.259  -1.303   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.695  -3.407   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.155  -0.739   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   10   17                                                       
CONECT   17   16    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0258257
HETATM    1  N1  UNL     1      -4.063   0.799  -0.922  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.492   1.342   0.272  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.001   1.242   0.343  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.499  -0.149   0.287  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.200  -1.329   0.181  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.295  -2.312   0.170  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.032  -1.819   0.265  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.208  -2.415   0.294  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.348  -1.628   0.400  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.239  -0.258   0.476  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.391   0.494   0.581  1.00  0.00           O  
HETATM   12  S1  UNL     1       4.253   1.092  -0.755  1.00  0.00           S  
HETATM   13  O2  UNL     1       3.708   2.464  -1.058  1.00  0.00           O  
HETATM   14  O3  UNL     1       4.151   0.184  -1.948  1.00  0.00           O  
HETATM   15  O4  UNL     1       5.872   1.242  -0.268  1.00  0.00           O  
HETATM   16  C9  UNL     1       1.002   0.338   0.447  1.00  0.00           C  
HETATM   17  C10 UNL     1      -0.149  -0.434   0.341  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.152   1.498  -1.691  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.939   0.258  -0.763  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.753   2.420   0.311  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.922   0.889   1.187  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.661   1.686   1.286  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.526   1.788  -0.508  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.289  -1.390   0.120  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.530  -3.327   0.097  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.295  -3.490   0.235  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.301  -2.149   0.419  1.00  0.00           H  
HETATM   28  H11 UNL     1       5.843   1.554   0.665  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.893   1.409   0.504  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5    5   17
CONECT    5    6   24
CONECT    6    7   25
CONECT    7    8    8   17
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11   16
CONECT   11   12
CONECT   12   13   13   14   14
CONECT   12   15
CONECT   15   28
CONECT   16   17   17   29
END

HMDB0258257
     RDKit          3D
Serotonin O-sulfate
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.0628    0.7995   -0.9219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924    1.3421    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0006    1.2419    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.1485    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -1.3292    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949   -2.3121    0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0323   -1.8188    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2080   -2.4148    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3477   -1.6277    0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390   -0.2581    0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3911    0.4938    0.5805 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    1.0917   -0.7550 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.7077    2.4638   -1.0576 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.1844   -1.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8718    1.2416   -0.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018    0.3380    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1493   -0.4337    0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518    1.4978   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    0.2577   -0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7531    2.4205    0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224    0.8889    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614    1.6858    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5265    1.7880   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2885   -1.3897    0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296   -3.3269    0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2952   -3.4902    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3012   -2.1494    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8426    1.5543    0.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930    1.4095    0.5044 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  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
 10 16  1  0
 16 17  2  0
 17  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 15 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[3-(2-Aminoethyl)-1H-indol-5-yl]oxidanesulfonate	Generator
[3-(2-Aminoethyl)-1H-indol-5-yl]oxidanesulphonate	Generator
[3-(2-Aminoethyl)-1H-indol-5-yl]oxidanesulphonic acid	Generator
5-Hydroxytryptamine O-sulfate	MeSH
5-Hydroxytryptamine O-sulfate, sulfate	MeSH
Serotonin sulfate	MeSH
Serotonin O-sulfuric acid	Generator
Serotonin O-sulphate	Generator
Serotonin O-sulphuric acid	Generator

Chemical Formula

C₁₀H₁₂N₂O₄S

Average Molecular Weight

256.28

Monoisotopic Molecular Weight

256.051778048

IUPAC Name

[3-(2-aminoethyl)-1H-indol-5-yl]oxidanesulfonic acid

Traditional Name

[3-(2-aminoethyl)-1H-indol-5-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

NCCC1=CNC2=CC=C(OS(O)(=O)=O)C=C12

InChI Identifier

InChI=1S/C10H12N2O4S/c11-4-3-7-6-12-10-2-1-8(5-9(7)10)16-17(13,14)15/h1-2,5-6,12H,3-4,11H2,(H,13,14,15)

InChI Key

JFWYSGGSCOOBGK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
Arylsulfate
3-alkylindole
Indole
2-arylethylamine
Aralkylamine
Substituted pyrrole
Sulfuric acid monoester
Benzenoid
Sulfuric acid ester
Sulfate-ester
Organic sulfuric acid or derivatives
Pyrrole
Heteroaromatic compound
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-11665 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	-0.91	ALOGPS
logP	-0.3	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	9.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.35 m³·mol⁻¹	ChemAxon
Polarizability	24.58 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M-2H]-	186.186	30932474
DeepCCS	[M+Na]+	161.928	30932474
AllCCS	[M+H]+	156.7	32859911
AllCCS	[M+H-H2O]+	153.2	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	152.1	32859911
AllCCS	[M+Na-2H]-	152.2	32859911
AllCCS	[M+HCOO]-	152.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Serotonin O-sulfate	NCCC1=CNC2=CC=C(OS(O)(=O)=O)C=C12	3828.2	Standard polar	33892256
Serotonin O-sulfate	NCCC1=CNC2=CC=C(OS(O)(=O)=O)C=C12	2336.2	Standard non polar	33892256
Serotonin O-sulfate	NCCC1=CNC2=CC=C(OS(O)(=O)=O)C=C12	2660.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Serotonin O-sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN)C2=C1	2484.3	Semi standard non polar	33892256
Serotonin O-sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN)C2=C1	2441.3	Standard non polar	33892256
Serotonin O-sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN)C2=C1	3836.7	Standard polar	33892256
Serotonin O-sulfate,1TMS,isomer #2	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12	2636.3	Semi standard non polar	33892256
Serotonin O-sulfate,1TMS,isomer #2	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12	2580.5	Standard non polar	33892256
Serotonin O-sulfate,1TMS,isomer #2	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12	3830.2	Standard polar	33892256
Serotonin O-sulfate,1TMS,isomer #3	C[Si](C)(C)N1C=C(CCN)C2=CC(OS(=O)(=O)O)=CC=C21	2533.8	Semi standard non polar	33892256
Serotonin O-sulfate,1TMS,isomer #3	C[Si](C)(C)N1C=C(CCN)C2=CC(OS(=O)(=O)O)=CC=C21	2503.7	Standard non polar	33892256
Serotonin O-sulfate,1TMS,isomer #3	C[Si](C)(C)N1C=C(CCN)C2=CC(OS(=O)(=O)O)=CC=C21	3937.7	Standard polar	33892256
Serotonin O-sulfate,2TMS,isomer #1	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C12	2603.4	Semi standard non polar	33892256
Serotonin O-sulfate,2TMS,isomer #1	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C12	2655.3	Standard non polar	33892256
Serotonin O-sulfate,2TMS,isomer #1	C[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C12	3422.5	Standard polar	33892256
Serotonin O-sulfate,2TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	2537.3	Semi standard non polar	33892256
Serotonin O-sulfate,2TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	2599.8	Standard non polar	33892256
Serotonin O-sulfate,2TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	3553.0	Standard polar	33892256
Serotonin O-sulfate,2TMS,isomer #3	C[Si](C)(C)N(CCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C	2773.5	Semi standard non polar	33892256
Serotonin O-sulfate,2TMS,isomer #3	C[Si](C)(C)N(CCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C	2764.3	Standard non polar	33892256
Serotonin O-sulfate,2TMS,isomer #3	C[Si](C)(C)N(CCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C	3609.7	Standard polar	33892256
Serotonin O-sulfate,2TMS,isomer #4	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12	2663.8	Semi standard non polar	33892256
Serotonin O-sulfate,2TMS,isomer #4	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12	2694.6	Standard non polar	33892256
Serotonin O-sulfate,2TMS,isomer #4	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12	3487.7	Standard polar	33892256
Serotonin O-sulfate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	2751.6	Semi standard non polar	33892256
Serotonin O-sulfate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	2843.2	Standard non polar	33892256
Serotonin O-sulfate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	3283.1	Standard polar	33892256
Serotonin O-sulfate,3TMS,isomer #2	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C12	2628.6	Semi standard non polar	33892256
Serotonin O-sulfate,3TMS,isomer #2	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C12	2766.3	Standard non polar	33892256
Serotonin O-sulfate,3TMS,isomer #2	C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C12	3200.7	Standard polar	33892256
Serotonin O-sulfate,3TMS,isomer #3	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C	2795.7	Semi standard non polar	33892256
Serotonin O-sulfate,3TMS,isomer #3	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C	2887.1	Standard non polar	33892256
Serotonin O-sulfate,3TMS,isomer #3	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C	3314.8	Standard polar	33892256
Serotonin O-sulfate,4TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2785.3	Semi standard non polar	33892256
Serotonin O-sulfate,4TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2951.6	Standard non polar	33892256
Serotonin O-sulfate,4TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	3129.1	Standard polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN)C2=C1	2745.6	Semi standard non polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN)C2=C1	2703.6	Standard non polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN)C2=C1	3816.7	Standard polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12	2920.2	Semi standard non polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12	2794.5	Standard non polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12	3816.4	Standard polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(CCN)C2=CC(OS(=O)(=O)O)=CC=C21	2821.9	Semi standard non polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(CCN)C2=CC(OS(=O)(=O)O)=CC=C21	2706.3	Standard non polar	33892256
Serotonin O-sulfate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(CCN)C2=CC(OS(=O)(=O)O)=CC=C21	3915.7	Standard polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C12	3148.9	Semi standard non polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C12	3129.1	Standard non polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C12	3443.7	Standard polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	3006.1	Semi standard non polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	3065.3	Standard non polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	3516.5	Standard polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C(C)(C)C	3269.5	Semi standard non polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C(C)(C)C	3184.5	Standard non polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C(C)(C)C	3572.6	Standard polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12	3191.4	Semi standard non polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12	3107.8	Standard non polar	33892256
Serotonin O-sulfate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12	3501.8	Standard polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3470.4	Semi standard non polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3512.1	Standard non polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	3385.4	Standard polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C12	3369.2	Semi standard non polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C12	3436.6	Standard non polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C12	3352.9	Standard polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C(C)(C)C	3509.4	Semi standard non polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C(C)(C)C	3505.1	Standard non polar	33892256
Serotonin O-sulfate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)O)C=C12)[Si](C)(C)C(C)(C)C	3410.0	Standard polar	33892256
Serotonin O-sulfate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3675.3	Semi standard non polar	33892256
Serotonin O-sulfate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3807.8	Standard non polar	33892256
Serotonin O-sulfate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3322.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin O-sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9660000000-c048038b5f9758bd927a	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Serotonin O-sulfate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Serotonin O-sulfate 10V, Negative-QTOF	splash10-0a4i-0090000000-ea1ac187e7d53047e236	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

134104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Serotonin O-sulfate (HMDB0258257)

MOL for HMDB0258257 (Serotonin O-sulfate)

3D MOL for HMDB0258257 (Serotonin O-sulfate)

3D SDF for HMDB0258257 (Serotonin O-sulfate)

3D-SDF for HMDB0258257 (Serotonin O-sulfate)

PDB for HMDB0258257 (Serotonin O-sulfate)

3D PDB for HMDB0258257 (Serotonin O-sulfate)

SMILES for HMDB0258257 (Serotonin O-sulfate)

INCHI for HMDB0258257 (Serotonin O-sulfate)

Structure for HMDB0258257 (Serotonin O-sulfate)

3D Structure for HMDB0258257 (Serotonin O-sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra