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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:31:27 UTC

Update Date

2021-09-26 23:12:53 UTC

HMDB ID

HMDB0256899

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Psilocybine

Description

Psilocybin, also known as indocybin, 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. Psilocybin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Psilocybin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Psilocybine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Psilocybine 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

HMDB0256899
     RDKit          3D
Psilocybine
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.8661    0.1244   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6942    0.2645    0.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922    0.9168    1.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7164    1.0717   -0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    0.3299   -1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063   -0.9373   -0.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -2.2133   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993   -3.1071   -0.4784 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422   -2.4960   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400   -2.9254    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -2.0647    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9664   -0.7197    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7873   -0.2552   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433    1.0897   -0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636    2.2301   -0.0003 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3276    2.2241    1.4394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108    1.8122   -0.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714    3.7500   -0.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477   -1.1484   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    0.4621    0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326   -0.9799   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7067    0.6222   -1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828    0.3809    2.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6213    1.9732    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    0.9158    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1694    2.0024   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8915    1.3558    0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9092    0.2056   -2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369    1.0117   -1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0700   -2.4356   -1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036   -4.1572   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841   -3.9900    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1244   -2.3813    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7501    0.0220    0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    2.5604   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064    4.4858   -0.0958 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 13 19  2  0
 19  6  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv0541 02241205392D          

 19 20  0  0  0  0            999 V2000
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   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
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9398   -3.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7648   -2.0460    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 13 19  2  0  0  0  0
  6 19  1  0  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256899

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

> <INCHI_KEY>
QVDSEJDULKLHCG-UHFFFAOYSA-N

> <FORMULA>
C12H17N2O4P

> <MOLECULAR_WEIGHT>
284.2481

> <EXACT_MASS>
284.092593554

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.820584823426547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
-0.1363668296579714

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.714547579942403

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7443777657361865

> <JCHEM_PKA_STRONGEST_BASIC>
9.536625544579383

> <JCHEM_POLAR_SURFACE_AREA>
85.78999999999999

> <JCHEM_REFRACTIVITY>
73.29599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
psilocybin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256899
     RDKit          3D
Psilocybine
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.8661    0.1244   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6942    0.2645    0.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922    0.9168    1.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7164    1.0717   -0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    0.3299   -1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063   -0.9373   -0.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -2.2133   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993   -3.1071   -0.4784 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422   -2.4960   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400   -2.9254    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -2.0647    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9664   -0.7197    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7873   -0.2552   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433    1.0897   -0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636    2.2301   -0.0003 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3276    2.2241    1.4394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108    1.8122   -0.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714    3.7500   -0.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477   -1.1484   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    0.4621    0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326   -0.9799   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7067    0.6222   -1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828    0.3809    2.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6213    1.9732    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    0.9158    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1694    2.0024   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8915    1.3558    0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9092    0.2056   -2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369    1.0117   -1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0700   -2.4356   -1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036   -4.1572   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841   -3.9900    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1244   -2.3813    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7501    0.0220    0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    2.5604   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064    4.4858   -0.0958 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 13 19  2  0
 19  6  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 17 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.332  -5.798   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.143  -4.333   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0       6.258  -5.153   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0       7.591  -5.923   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.488  -6.486   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.028  -3.819   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   13    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0256899
HETATM    1  C1  UNL     1       3.866   0.124  -0.222  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.694   0.264   0.622  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.992   0.917   1.877  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.716   1.072  -0.077  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.163   0.330  -1.289  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.506  -0.937  -0.889  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.086  -2.213  -0.952  1.00  0.00           C  
HETATM    8  N2  UNL     1       0.199  -3.107  -0.478  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.942  -2.496  -0.104  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.140  -2.925   0.426  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.187  -2.065   0.721  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.966  -0.720   0.452  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.787  -0.255  -0.074  1.00  0.00           C  
HETATM   14  O1  UNL     1      -1.643   1.090  -0.316  1.00  0.00           O  
HETATM   15  P1  UNL     1      -2.864   2.230  -0.000  1.00  0.00           P  
HETATM   16  O2  UNL     1      -3.328   2.224   1.439  1.00  0.00           O  
HETATM   17  O3  UNL     1      -4.211   1.812  -0.956  1.00  0.00           O  
HETATM   18  O4  UNL     1      -2.271   3.750  -0.465  1.00  0.00           O  
HETATM   19  C12 UNL     1      -0.748  -1.148  -0.361  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.796   0.462   0.280  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.933  -0.980  -0.451  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.707   0.622  -1.211  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.483   0.381   2.698  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.621   1.973   1.857  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.094   0.916   2.017  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.169   2.002  -0.480  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.892   1.356   0.582  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.909   0.206  -2.079  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.337   1.012  -1.660  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.070  -2.436  -1.318  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.304  -4.157  -0.381  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.284  -3.990   0.627  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.124  -2.381   1.135  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.750   0.022   0.661  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.485   2.560  -1.536  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.806   4.486  -0.096  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7    7   19
CONECT    7    8   30
CONECT    8    9   31
CONECT    9   10   10   19
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13   34
CONECT   13   14   19   19
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   35
CONECT   18   36
END

HMDB0256899
     RDKit          3D
Psilocybine
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.8661    0.1244   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6942    0.2645    0.6225 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922    0.9168    1.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7164    1.0717   -0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    0.3299   -1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063   -0.9373   -0.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -2.2133   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993   -3.1071   -0.4784 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422   -2.4960   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400   -2.9254    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -2.0647    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9664   -0.7197    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7873   -0.2552   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433    1.0897   -0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636    2.2301   -0.0003 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.3276    2.2241    1.4394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108    1.8122   -0.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714    3.7500   -0.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477   -1.1484   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    0.4621    0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326   -0.9799   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7067    0.6222   -1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828    0.3809    2.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6213    1.9732    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    0.9158    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1694    2.0024   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8915    1.3558    0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9092    0.2056   -2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369    1.0117   -1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0700   -2.4356   -1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036   -4.1572   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841   -3.9900    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1244   -2.3813    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7501    0.0220    0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    2.5604   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064    4.4858   -0.0958 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 13 19  2  0
 19  6  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate ester	ChEBI
3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphate	ChEBI
4-Phosphoryloxy-N,N-dimethyltryptamine	ChEBI
Indocybin	ChEBI
O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine	ChEBI
Psilocibina	ChEBI
Psilocin phosphate ester	ChEBI
Psilocybine	ChEBI
Psilocybinum	ChEBI
3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphoric acid ester	Generator
3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphoric acid	Generator
Psilocin phosphoric acid ester	Generator
Psilocibin	MeSH

Chemical Formula

C₁₂H₁₇N₂O₄P

Average Molecular Weight

284.2481

Monoisotopic Molecular Weight

284.092593554

IUPAC Name

({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid

Traditional Name

psilocybin

CAS Registry Number

Not Available

SMILES

CN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12

InChI Identifier

InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

InChI Key

QVDSEJDULKLHCG-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
Aryl phosphate
Aryl phosphomonoester
3-alkylindole
Indole
Alkaloid or derivatives
Aralkylamine
Organic phosphoric acid derivative
Phosphoric acid ester
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:8614 )
organic phosphate (CHEBI:8614 )
tryptamine alkaloid (CHEBI:8614 )
Alkaloids (C07576 )

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	1.25	ALOGPS
logP	-0.14	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.3 m³·mol⁻¹	ChemAxon
Polarizability	27.82 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]-	187.284	30932474
DeepCCS	[M+Na]+	163.32	30932474
AllCCS	[M+H]+	164.1	32859911
AllCCS	[M+H-H2O]+	160.6	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	168.3	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	163.8	32859911
AllCCS	[M+HCOO]-	163.9	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.	3.94 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2743 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.99 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	393.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	251.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	296.7 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	268.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	965.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	607.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	534.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	164.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	927.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	576.6 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	334.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Psilocybine	CN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12	3346.1	Standard polar	33892256
Psilocybine	CN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12	2272.7	Standard non polar	33892256
Psilocybine	CN(C)CCC1=CNC2=CC=CC(OP(O)(O)=O)=C12	2596.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Psilocybine,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O)O[Si](C)(C)C)=C12	2368.2	Semi standard non polar	33892256
Psilocybine,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O)O[Si](C)(C)C)=C12	2475.6	Standard non polar	33892256
Psilocybine,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O)O[Si](C)(C)C)=C12	3065.5	Standard polar	33892256
Psilocybine,1TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O)O)=C12	2412.2	Semi standard non polar	33892256
Psilocybine,1TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O)O)=C12	2459.2	Standard non polar	33892256
Psilocybine,1TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O)O)=C12	3181.5	Standard polar	33892256
Psilocybine,2TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C12	2409.3	Semi standard non polar	33892256
Psilocybine,2TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C12	2546.3	Standard non polar	33892256
Psilocybine,2TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C12	2759.2	Standard polar	33892256
Psilocybine,2TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O)O[Si](C)(C)C)=C12	2393.9	Semi standard non polar	33892256
Psilocybine,2TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O)O[Si](C)(C)C)=C12	2501.1	Standard non polar	33892256
Psilocybine,2TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O)O[Si](C)(C)C)=C12	2896.9	Standard polar	33892256
Psilocybine,3TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C12	2459.1	Semi standard non polar	33892256
Psilocybine,3TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C12	2551.6	Standard non polar	33892256
Psilocybine,3TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C12	2693.4	Standard polar	33892256
Psilocybine,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C12	2590.2	Semi standard non polar	33892256
Psilocybine,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C12	2679.8	Standard non polar	33892256
Psilocybine,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C12	3204.1	Standard polar	33892256
Psilocybine,1TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O)O)=C12	2643.5	Semi standard non polar	33892256
Psilocybine,1TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O)O)=C12	2633.4	Standard non polar	33892256
Psilocybine,1TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O)O)=C12	3229.0	Standard polar	33892256
Psilocybine,2TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12	2810.2	Semi standard non polar	33892256
Psilocybine,2TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12	2934.5	Standard non polar	33892256
Psilocybine,2TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12	3014.2	Standard polar	33892256
Psilocybine,2TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C12	2811.6	Semi standard non polar	33892256
Psilocybine,2TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C12	2869.3	Standard non polar	33892256
Psilocybine,2TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C12	3083.7	Standard polar	33892256
Psilocybine,3TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12	3022.7	Semi standard non polar	33892256
Psilocybine,3TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12	3045.9	Standard non polar	33892256
Psilocybine,3TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C12	2984.0	Standard polar	33892256

Spectra

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

DB11664

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00051822

Chemspider ID

10178

KEGG Compound ID

C07576

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Psilocybin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

8614

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 Psilocybine (HMDB0256899)

MOL for HMDB0256899 (Psilocybine)

3D MOL for HMDB0256899 (Psilocybine)

3D SDF for HMDB0256899 (Psilocybine)

3D-SDF for HMDB0256899 (Psilocybine)

PDB for HMDB0256899 (Psilocybine)

3D PDB for HMDB0256899 (Psilocybine)

SMILES for HMDB0256899 (Psilocybine)

INCHI for HMDB0256899 (Psilocybine)

Structure for HMDB0256899 (Psilocybine)

3D Structure for HMDB0256899 (Psilocybine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized