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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:27:32 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254261

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lysergamide

Description

Lysergamide belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. Based on a literature review a significant number of articles have been published on Lysergamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lysergamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lysergamide 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

HMDB0254261
     RDKit          3D
LYSERGAMIDE
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.7257   -2.8130    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4503   -1.4557   -0.0491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -0.5873    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261    0.6903   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3433    1.7369   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7475    1.6271   -0.1239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695    2.8147    0.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    1.1882   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    0.4597   -0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    1.0181    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    2.3671    0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    2.7461    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140    1.8128    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6713    0.4432    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058   -0.6857    0.1726 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348   -1.7272    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -1.2499    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    0.0979    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876   -1.8558    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.9512    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520   -3.0587    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168   -3.4621   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -3.0195    0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -0.4265    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4850   -1.1365   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300    0.4661   -1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2797    1.6553    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2376    1.5187   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135    2.2118   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    3.0546   -0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316    3.8140    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    2.1334    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302   -0.7332    0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7849   -2.7878    0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9032   -2.7313    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364   -2.2756   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2101   -0.8988    1.5947 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
  5  7  2  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20  2  1  0
 20  9  1  0
 18 10  1  0
 18 14  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
M  END

  Mrv0541 02241212292D          

 20 23  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
   -1.5605   -3.8661    0.0000 N   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  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254261

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)

> <INCHI_KEY>
GENAHGKEFJLNJB-UHFFFAOYSA-N

> <FORMULA>
C16H17N3O

> <MOLECULAR_WEIGHT>
267.3257

> <EXACT_MASS>
267.137162181

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.340927611747066

> <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-pentaene-4-carboxamide

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.1205469073333338

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.12792046144603

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.337583598067123

> <JCHEM_PKA_STRONGEST_BASIC>
8.053320517215887

> <JCHEM_POLAR_SURFACE_AREA>
62.120000000000005

> <JCHEM_REFRACTIVITY>
79.44409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254261
     RDKit          3D
LYSERGAMIDE
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.7257   -2.8130    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4503   -1.4557   -0.0491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -0.5873    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261    0.6903   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3433    1.7369   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7475    1.6271   -0.1239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695    2.8147    0.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    1.1882   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    0.4597   -0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    1.0181    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    2.3671    0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    2.7461    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140    1.8128    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6713    0.4432    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058   -0.6857    0.1726 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348   -1.7272    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -1.2499    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    0.0979    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876   -1.8558    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.9512    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520   -3.0587    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168   -3.4621   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -3.0195    0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -0.4265    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4850   -1.1365   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300    0.4661   -1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2797    1.6553    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2376    1.5187   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135    2.2118   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    3.0546   -0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316    3.8140    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    2.1334    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302   -0.7332    0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7849   -2.7878    0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9032   -2.7313    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364   -2.2756   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2101   -0.8988    1.5947 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
  5  7  2  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20  2  1  0
 20  9  1  0
 18 10  1  0
 18 14  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 20 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
HETATM   20  N   UNK     0      -2.913  -7.217   0.000  0.00  0.00           N+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   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0254261
HETATM    1  C1  UNL     1      -1.726  -2.813   0.306  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.450  -1.456  -0.049  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.583  -0.587   0.202  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.426   0.690  -0.552  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.343   1.737  -0.095  1.00  0.00           C  
HETATM    6  N2  UNL     1      -4.748   1.627  -0.124  1.00  0.00           N  
HETATM    7  O1  UNL     1      -2.870   2.815   0.357  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.015   1.188  -0.478  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.055   0.460  -0.014  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.316   1.018   0.031  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.561   2.367   0.027  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.896   2.746   0.075  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.914   1.813   0.125  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.671   0.443   0.129  1.00  0.00           C  
HETATM   15  N3  UNL     1       4.406  -0.686   0.173  1.00  0.00           N  
HETATM   16  C12 UNL     1       3.535  -1.727   0.151  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.224  -1.250   0.093  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.338   0.098   0.080  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.888  -1.856   0.047  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.229  -0.951   0.487  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.552  -3.059   1.358  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.117  -3.462  -0.387  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.800  -3.019   0.060  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.751  -0.427   1.283  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.485  -1.137  -0.189  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.630   0.466  -1.633  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.280   1.655   0.760  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.238   1.519  -1.032  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.814   2.212  -0.842  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.739   3.055  -0.008  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.132   3.814   0.073  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.947   2.133   0.162  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.430  -0.733   0.214  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.785  -2.788   0.174  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.903  -2.731   0.746  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.636  -2.276  -0.954  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.210  -0.899   1.595  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   20
CONECT    3    4   24   25
CONECT    4    5    8   26
CONECT    5    6    7    7
CONECT    6   27   28
CONECT    8    9    9   29
CONECT    9   10   20
CONECT   10   11   11   18
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   14   32
CONECT   14   15   18   18
CONECT   15   16   33
CONECT   16   17   17   34
CONECT   17   18   19
CONECT   19   20   35   36
CONECT   20   37
END

HMDB0254261
     RDKit          3D
LYSERGAMIDE
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.7257   -2.8130    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4503   -1.4557   -0.0491 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -0.5873    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261    0.6903   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3433    1.7369   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7475    1.6271   -0.1239 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695    2.8147    0.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    1.1882   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    0.4597   -0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    1.0181    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    2.3671    0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    2.7461    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140    1.8128    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6713    0.4432    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058   -0.6857    0.1726 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5348   -1.7272    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -1.2499    0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    0.0979    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876   -1.8558    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.9512    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520   -3.0587    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168   -3.4621   -0.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -3.0195    0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -0.4265    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4850   -1.1365   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300    0.4661   -1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2797    1.6553    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2376    1.5187   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135    2.2118   -0.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389    3.0546   -0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316    3.8140    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    2.1334    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302   -0.7332    0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7849   -2.7878    0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9032   -2.7313    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364   -2.2756   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2101   -0.8988    1.5947 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
  5  7  2  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20  2  1  0
 20  9  1  0
 18 10  1  0
 18 14  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lysergic acid amide	HMDB
9,10-Didehydro-6-methylergoline-8 beta-carboxamide	HMDB

Chemical Formula

C₁₆H₁₇N₃O

Average Molecular Weight

267.3257

Monoisotopic Molecular Weight

267.137162181

IUPAC Name

6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

Traditional Name

6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

CAS Registry Number

Not Available

SMILES

CN1CC(C=C2C1CC1=CNC3=CC=CC2=C13)C(N)=O

InChI Identifier

InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)

InChI Key

GENAHGKEFJLNJB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Lysergamides

Alternative Parents

Substituents

Lysergic acid amide
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline-3-carboxamide
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Primary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Amine
Organopnictogen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organic oxide
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	1.53	ALOGPS
logP	1.12	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	16.34	ChemAxon
pKa (Strongest Basic)	8.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.44 m³·mol⁻¹	ChemAxon
Polarizability	29.34 Å³	ChemAxon
Number of Rings	4	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]-	191.598	30932474
DeepCCS	[M+Na]+	166.825	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.5	32859911
AllCCS	[M+NH4]+	166.4	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	167.6	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	166.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
LYSERGAMIDE	CN1CC(C=C2C1CC1=CNC3=CC=CC2=C13)C(N)=O	4209.2	Standard polar	33892256
LYSERGAMIDE	CN1CC(C=C2C1CC1=CNC3=CC=CC2=C13)C(N)=O	2810.2	Standard non polar	33892256
LYSERGAMIDE	CN1CC(C=C2C1CC1=CNC3=CC=CC2=C13)C(N)=O	3147.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
LYSERGAMIDE,1TMS,isomer #1	CN1CC(C(=O)N[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2729.8	Semi standard non polar	33892256
LYSERGAMIDE,1TMS,isomer #1	CN1CC(C(=O)N[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2745.7	Standard non polar	33892256
LYSERGAMIDE,1TMS,isomer #1	CN1CC(C(=O)N[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	3577.5	Standard polar	33892256
LYSERGAMIDE,1TMS,isomer #2	CN1CC(C(N)=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2812.4	Semi standard non polar	33892256
LYSERGAMIDE,1TMS,isomer #2	CN1CC(C(N)=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2744.6	Standard non polar	33892256
LYSERGAMIDE,1TMS,isomer #2	CN1CC(C(N)=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	3929.9	Standard polar	33892256
LYSERGAMIDE,2TMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2812.3	Semi standard non polar	33892256
LYSERGAMIDE,2TMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2899.6	Standard non polar	33892256
LYSERGAMIDE,2TMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	3506.7	Standard polar	33892256
LYSERGAMIDE,2TMS,isomer #2	CN1CC(C(=O)N[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2734.5	Semi standard non polar	33892256
LYSERGAMIDE,2TMS,isomer #2	CN1CC(C(=O)N[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2817.3	Standard non polar	33892256
LYSERGAMIDE,2TMS,isomer #2	CN1CC(C(=O)N[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	3411.7	Standard polar	33892256
LYSERGAMIDE,3TMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2815.5	Semi standard non polar	33892256
LYSERGAMIDE,3TMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2958.3	Standard non polar	33892256
LYSERGAMIDE,3TMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	3297.8	Standard polar	33892256
LYSERGAMIDE,1TBDMS,isomer #1	CN1CC(C(=O)N[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2972.8	Semi standard non polar	33892256
LYSERGAMIDE,1TBDMS,isomer #1	CN1CC(C(=O)N[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2993.7	Standard non polar	33892256
LYSERGAMIDE,1TBDMS,isomer #1	CN1CC(C(=O)N[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	3683.1	Standard polar	33892256
LYSERGAMIDE,1TBDMS,isomer #2	CN1CC(C(N)=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3052.4	Semi standard non polar	33892256
LYSERGAMIDE,1TBDMS,isomer #2	CN1CC(C(N)=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	2950.7	Standard non polar	33892256
LYSERGAMIDE,1TBDMS,isomer #2	CN1CC(C(N)=O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	4007.0	Standard polar	33892256
LYSERGAMIDE,2TBDMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	3201.1	Semi standard non polar	33892256
LYSERGAMIDE,2TBDMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	3404.9	Standard non polar	33892256
LYSERGAMIDE,2TBDMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	3608.8	Standard polar	33892256
LYSERGAMIDE,2TBDMS,isomer #2	CN1CC(C(=O)N[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3148.3	Semi standard non polar	33892256
LYSERGAMIDE,2TBDMS,isomer #2	CN1CC(C(=O)N[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3295.9	Standard non polar	33892256
LYSERGAMIDE,2TBDMS,isomer #2	CN1CC(C(=O)N[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3563.9	Standard polar	33892256
LYSERGAMIDE,3TBDMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3381.2	Semi standard non polar	33892256
LYSERGAMIDE,3TBDMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3661.7	Standard non polar	33892256
LYSERGAMIDE,3TBDMS,isomer #1	CN1CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3496.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lysergamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1930000000-96f17ffa0a83413ec7a5	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lysergamide 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 - Lysergamide 10V, Positive-QTOF	splash10-014i-0090000000-8fad01136a8b199a8fcb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 20V, Positive-QTOF	splash10-0udi-0190000000-985cc814d0e193c43684	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 40V, Positive-QTOF	splash10-0gbc-1910000000-dce49447127bea0dfea1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 10V, Negative-QTOF	splash10-014i-0090000000-87f8f855a2a94e8a889d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 20V, Negative-QTOF	splash10-01b9-2090000000-16b0b0b2f013883fce73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 40V, Negative-QTOF	splash10-0006-9120000000-ff89d0d78a1a5021bbc8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 10V, Positive-QTOF	splash10-014i-0090000000-2fbac29c568b505e00c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 20V, Positive-QTOF	splash10-01b9-0190000000-7c94bf3c4efe46898ad5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 40V, Positive-QTOF	splash10-01c0-1950000000-ca6fdeb0ee82d291c592	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 10V, Negative-QTOF	splash10-014i-0090000000-bcc089403fa9e763217c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 20V, Negative-QTOF	splash10-014i-3090000000-0cb408041c452248a52a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lysergamide 40V, Negative-QTOF	splash10-0006-8390000000-a13d638b9f0cb1dfb070	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

9767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergine

METLIN ID

Not Available

PubChem Compound

10173

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 Lysergamide (HMDB0254261)

MOL for HMDB0254261 (Lysergamide)

3D MOL for HMDB0254261 (Lysergamide)

3D SDF for HMDB0254261 (Lysergamide)

3D-SDF for HMDB0254261 (Lysergamide)

PDB for HMDB0254261 (Lysergamide)

3D PDB for HMDB0254261 (Lysergamide)

SMILES for HMDB0254261 (Lysergamide)

INCHI for HMDB0254261 (Lysergamide)

Structure for HMDB0254261 (Lysergamide)

3D Structure for HMDB0254261 (Lysergamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra