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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:27:34 UTC

Update Date

2021-09-26 23:07:02 UTC

HMDB ID

HMDB0253658

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isolysergol

Description

Lysergol belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines. Lysergol is a very strong basic compound (based on its pKa). Lysergol is a potentially toxic compound. Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Usually the gastrointestinal effects precede the central nervous system effects. Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi (most within Claviceps), and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea. Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isolysergol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isolysergol 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

HMDB0254264
     RDKit          3D
lysergol
 37 40  0  0  0  0  0  0  0  0999 V2000
    2.1218    2.3859    0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737    1.0747    0.3213 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4912    0.7591   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601   -0.7176   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2452   -1.5190   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697   -1.3033    1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -1.1752   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547   -0.5016   -0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.9607   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -2.2898   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988   -2.6075   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -1.6211    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -0.3018    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.8729    0.6902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921    1.8705    0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606    1.3165    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -0.0099    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    1.7868    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    0.7125    0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    2.4871    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    2.5419    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944    3.1311    0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1491    1.3907   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5784    0.9578   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -0.8678   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837   -1.1923   -0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1367   -2.5833   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -2.1378    1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318   -2.0437   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8687   -3.0181   -0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2808   -3.6079   -0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8755   -1.8624    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0548    0.9623    0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    2.9024    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149    1.9867   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    2.7462    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3491    0.4356    1.5394 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  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  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
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 19  8  1  0
 17  9  1  0
 17 13  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

  Mrv0541 02241212302D          

 19 22  0  0  0  0            999 V2000
   -2.2715   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -1.3911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585   -2.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8445   -2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -2.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8455   -3.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -3.8679    0.0000 O   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  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  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  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
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253658

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CC(CO)C=C2C1CC1=CNC3=CC=CC2=C13

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3

> <INCHI_KEY>
BIXJFIJYBLJTMK-UHFFFAOYSA-N

> <FORMULA>
C16H18N2O

> <MOLECULAR_WEIGHT>
254.3269

> <EXACT_MASS>
254.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.832785088229976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-yl}methanol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.518688484333333

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.037243950734204

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.382463847168651

> <JCHEM_PKA_STRONGEST_BASIC>
7.930318605766813

> <JCHEM_POLAR_SURFACE_AREA>
39.260000000000005

> <JCHEM_REFRACTIVITY>
77.83749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lysergol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254264
     RDKit          3D
lysergol
 37 40  0  0  0  0  0  0  0  0999 V2000
    2.1218    2.3859    0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737    1.0747    0.3213 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4912    0.7591   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601   -0.7176   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2452   -1.5190   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697   -1.3033    1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -1.1752   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547   -0.5016   -0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.9607   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -2.2898   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988   -2.6075   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -1.6211    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -0.3018    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.8729    0.6902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921    1.8705    0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606    1.3165    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -0.0099    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    1.7868    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    0.7125    0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    2.4871    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    2.5419    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944    3.1311    0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1491    1.3907   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5784    0.9578   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -0.8678   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837   -1.1923   -0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1367   -2.5833   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -2.1378    1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318   -2.0437   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8687   -3.0181   -0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2808   -3.6079   -0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8755   -1.8624    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0548    0.9623    0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    2.9024    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149    1.9867   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    2.7462    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3491    0.4356    1.5394 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  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  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
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 19  8  1  0
 17  9  1  0
 17 13  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  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      -4.240  -1.825   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.907  -2.597   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.909  -4.137   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.576  -4.908   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.242  -4.140   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.573  -1.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.578  -6.448   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.245  -7.220   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   17                                                  
CONECT   17   16    9   12                                                  
CONECT   18    4   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0254264
HETATM    1  C1  UNL     1       2.122   2.386   0.806  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.874   1.075   0.321  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.491   0.759  -0.921  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.360  -0.718  -1.237  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.245  -1.519  -0.307  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.870  -1.303   1.023  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.957  -1.175  -1.089  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.155  -0.502  -0.328  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.239  -0.961  -0.186  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.575  -2.290  -0.376  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.899  -2.607  -0.184  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.834  -1.621   0.184  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.460  -0.302   0.363  1.00  0.00           C  
HETATM   14  N2  UNL     1      -4.029   0.873   0.690  1.00  0.00           N  
HETATM   15  C12 UNL     1      -3.092   1.871   0.696  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.861   1.316   0.357  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.145  -0.010   0.167  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.476   1.787   0.149  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.493   0.712   0.454  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.172   2.487   1.170  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.484   2.542   1.715  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.894   3.131   0.019  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.149   1.391  -1.771  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.578   0.958  -0.818  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.748  -0.868  -2.266  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.284  -1.192  -0.414  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.137  -2.583  -0.539  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.644  -2.138   1.477  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.632  -2.044  -1.606  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.869  -3.018  -0.652  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.281  -3.608  -0.302  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.876  -1.862   0.337  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.055   0.962   0.903  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.263   2.902   0.919  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.415   1.987  -0.967  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.270   2.746   0.672  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.349   0.436   1.539  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   19
CONECT    3    4   23   24
CONECT    4    5    7   25
CONECT    5    6   26   27
CONECT    6   28
CONECT    7    8    8   29
CONECT    8    9   19
CONECT    9   10   10   17
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   12   13   32
CONECT   13   14   17   17
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   18
CONECT   18   19   35   36
CONECT   19   37
END

HMDB0254264
     RDKit          3D
lysergol
 37 40  0  0  0  0  0  0  0  0999 V2000
    2.1218    2.3859    0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737    1.0747    0.3213 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4912    0.7591   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601   -0.7176   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2452   -1.5190   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697   -1.3033    1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9571   -1.1752   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547   -0.5016   -0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.9607   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748   -2.2898   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988   -2.6075   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -1.6211    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -0.3018    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.8729    0.6902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921    1.8705    0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606    1.3165    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -0.0099    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    1.7868    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    0.7125    0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    2.4871    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    2.5419    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944    3.1311    0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1491    1.3907   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5784    0.9578   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -0.8678   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837   -1.1923   -0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1367   -2.5833   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -2.1378    1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318   -2.0437   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8687   -3.0181   -0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2808   -3.6079   -0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8755   -1.8624    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0548    0.9623    0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    2.9024    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149    1.9867   -0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    2.7462    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3491    0.4356    1.5394 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  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  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
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19  2  1  0
 19  8  1  0
 17  9  1  0
 17 13  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lysergol, (8alpha)-isomer	MeSH
Isolysergol	MeSH

Chemical Formula

C₁₆H₁₈N₂O

Average Molecular Weight

254.3269

Monoisotopic Molecular Weight

254.141913208

IUPAC Name

{6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-yl}methanol

Traditional Name

lysergol

CAS Registry Number

Not Available

SMILES

CN1CC(CO)C=C2C1CC1=CNC3=CC=CC2=C13

InChI Identifier

InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3

InChI Key

BIXJFIJYBLJTMK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Clavines and derivatives

Direct Parent

Clavines and derivatives

Alternative Parents

Substituents

Clavine skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Alcohol
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.17	ALOGPS
logP	1.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	15.38	ChemAxon
pKa (Strongest Basic)	7.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.84 m³·mol⁻¹	ChemAxon
Polarizability	28.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	194.282	30932474
DeepCCS	[M+Na]+	170.184	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	156.4	32859911
AllCCS	[M+NH4]+	163.7	32859911
AllCCS	[M+Na]+	164.7	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	166.5	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isolysergol,1TMS,isomer #1	CN1CC(CO[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2519.8	Semi standard non polar	33892256
Isolysergol,1TMS,isomer #1	CN1CC(CO[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2575.5	Standard non polar	33892256
Isolysergol,1TMS,isomer #1	CN1CC(CO[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	3254.8	Standard polar	33892256
Isolysergol,1TMS,isomer #2	CN1CC(CO)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2550.1	Semi standard non polar	33892256
Isolysergol,1TMS,isomer #2	CN1CC(CO)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2612.1	Standard non polar	33892256
Isolysergol,1TMS,isomer #2	CN1CC(CO)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	3383.2	Standard polar	33892256
Isolysergol,2TMS,isomer #1	CN1CC(CO[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2505.7	Semi standard non polar	33892256
Isolysergol,2TMS,isomer #1	CN1CC(CO[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2674.9	Standard non polar	33892256
Isolysergol,2TMS,isomer #1	CN1CC(CO[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	3094.5	Standard polar	33892256
Isolysergol,1TBDMS,isomer #1	CN1CC(CO[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2774.1	Semi standard non polar	33892256
Isolysergol,1TBDMS,isomer #1	CN1CC(CO[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2826.6	Standard non polar	33892256
Isolysergol,1TBDMS,isomer #1	CN1CC(CO[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	3395.5	Standard polar	33892256
Isolysergol,1TBDMS,isomer #2	CN1CC(CO)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	2802.7	Semi standard non polar	33892256
Isolysergol,1TBDMS,isomer #2	CN1CC(CO)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	2839.5	Standard non polar	33892256
Isolysergol,1TBDMS,isomer #2	CN1CC(CO)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3498.9	Standard polar	33892256
Isolysergol,2TBDMS,isomer #1	CN1CC(CO[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	2961.0	Semi standard non polar	33892256
Isolysergol,2TBDMS,isomer #1	CN1CC(CO[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3152.3	Standard non polar	33892256
Isolysergol,2TBDMS,isomer #1	CN1CC(CO[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3279.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isolysergol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v4s-0980000000-d6088512e6e088db65fe	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isolysergol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isolysergol 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 - Isolysergol 10V, Positive-QTOF	splash10-0a4r-0090000000-22a043029f9b70281d83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 20V, Positive-QTOF	splash10-000i-0290000000-53b806358a6fe4205813	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 40V, Positive-QTOF	splash10-11ou-1930000000-82b6030ff03dc7953cab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 10V, Negative-QTOF	splash10-0udi-0090000000-bb5f88068da43d1909f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 20V, Negative-QTOF	splash10-0fk9-0090000000-af549c774e8bf93afd0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 40V, Negative-QTOF	splash10-0abd-3790000000-4dd23bb6f965aede9924	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 10V, Positive-QTOF	splash10-0a4i-0090000000-44486df23ca9fca419a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 20V, Positive-QTOF	splash10-0a4i-0290000000-5e6ede19f53579f80e8c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 40V, Positive-QTOF	splash10-06fr-0890000000-ddce0c7c262f4d63f9d7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 10V, Negative-QTOF	splash10-0udi-0090000000-6955ca0e1ca8673198f8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 20V, Negative-QTOF	splash10-0uk9-0090000000-08d5a41fbc48f37b31b0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolysergol 40V, Negative-QTOF	splash10-06di-0690000000-90d134e34545b3b68bf7	2021-10-12	Wishart Lab	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lysergol

METLIN ID

Not Available

PubChem Compound

3982

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 Isolysergol (HMDB0253658)

MOL for HMDB0253658 (Isolysergol)

3D MOL for HMDB0253658 (Isolysergol)

3D SDF for HMDB0253658 (Isolysergol)

3D-SDF for HMDB0253658 (Isolysergol)

PDB for HMDB0253658 (Isolysergol)

3D PDB for HMDB0253658 (Isolysergol)

SMILES for HMDB0253658 (Isolysergol)

INCHI for HMDB0253658 (Isolysergol)

Structure for HMDB0253658 (Isolysergol)

3D Structure for HMDB0253658 (Isolysergol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra