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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:09:45 UTC

Update Date

2022-03-07 02:53:42 UTC

HMDB ID

HMDB0033428

Secondary Accession Numbers

HMDB33428

Metabolite Identification

Common Name

(+)-Setoclavine

Description

(+)-Setoclavine 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 (+)-Setoclavine has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make (+)-setoclavine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (+)-Setoclavine.

Structure

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

HMDB0033428
     RDKit          3D
(+)-Setoclavine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.9026   -2.6811    0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510   -1.2870    0.6285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6829   -0.4561    0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.7873   -0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952    1.8888    0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    0.6043   -1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    1.3089   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178    0.4545   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551    0.9456   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516    2.2822   -0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    2.6021   -0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877    1.6461   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813    0.3101    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.8350    0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3305   -1.8514    0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494   -1.3072    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2276    0.0220    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -1.8713    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -0.9803   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743   -2.9510   -0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2661   -3.3648    1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -2.7798    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0718   -0.1852    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4891   -1.0471   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701    2.0846   -0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    2.8313    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919    1.5694    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.5172   -2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781    2.3589   -0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8314    3.0394   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247    3.6175   -0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9344    1.9226   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -0.9082    0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -2.8961    0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203   -2.2844    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629   -2.8173   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.2897   -1.2264 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
  4  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
  5 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 05061307072D          

 19 22  0  0  0  0            999 V2000
   -1.3756   -3.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715   -0.9778    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
    2.0143   -0.1554    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
   -0.1296   -2.2179    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
   -1.5585   -2.2161    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
    0.5839   -0.9804    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
    1.3018    0.2571    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
    0.5839   -0.1554    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
    0.9964    1.1143    0.0000 N   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
   -0.3150   -3.2621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  4  1  0  0  0  0
 12  7  2  0  0  0  0
 12 11  1  0  0  0  0
 13  5  2  0  0  0  0
 14  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16  1  1  0  0  0  0
 16  7  1  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
 18 14  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033428

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O/c1-16(19)7-12-11-4-3-5-13-15(11)10(8-17-13)6-14(12)18(2)9-16/h3-5,7-8,14,17,19H,6,9H2,1-2H3

> <INCHI_KEY>
BGVUWLLRNRBDAY-UHFFFAOYSA-N

> <FORMULA>
C16H18N2O

> <MOLECULAR_WEIGHT>
254.3269

> <EXACT_MASS>
254.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.964744101673052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-ol

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
1.9104180689999999

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.03116948606298

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.277900283837731

> <JCHEM_PKA_STRONGEST_BASIC>
7.9183014708795145

> <JCHEM_POLAR_SURFACE_AREA>
39.260000000000005

> <JCHEM_REFRACTIVITY>
77.3817

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033428
     RDKit          3D
(+)-Setoclavine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.9026   -2.6811    0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510   -1.2870    0.6285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6829   -0.4561    0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.7873   -0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952    1.8888    0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    0.6043   -1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    1.3089   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178    0.4545   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551    0.9456   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516    2.2822   -0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    2.6021   -0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877    1.6461   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813    0.3101    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.8350    0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3305   -1.8514    0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494   -1.3072    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2276    0.0220    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -1.8713    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -0.9803   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743   -2.9510   -0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2661   -3.3648    1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -2.7798    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0718   -0.1852    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4891   -1.0471   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701    2.0846   -0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    2.8313    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919    1.5694    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.5172   -2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781    2.3589   -0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8314    3.0394   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247    3.6175   -0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9344    1.9226   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -0.9082    0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -2.8961    0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203   -2.2844    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629   -2.8173   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.2897   -1.2264 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
  4  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
  5 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                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.568  -6.087   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.240  -1.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.242  -4.140   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.909  -4.137   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.573  -1.828   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.576  -4.908   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -2.907  -2.597   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -0.588  -6.089   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   18                                                            
CONECT    3    4    5                                                       
CONECT    4    3   11                                                       
CONECT    5    3   13                                                       
CONECT    6   10   14                                                       
CONECT    7   12   16                                                       
CONECT    8   10   17                                                       
CONECT    9   16   18                                                       
CONECT   10    6    8   15                                                  
CONECT   11    4   12   15                                                  
CONECT   12    7   11   14                                                  
CONECT   13    5   15   17                                                  
CONECT   14    6   12   18                                                  
CONECT   15   10   11   13                                                  
CONECT   16    1    7    9   19                                             
CONECT   17    8   13                                                       
CONECT   18    2    9   14                                                  
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0033428
HETATM    1  C1  UNL     1      -1.903  -2.681   0.447  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.551  -1.287   0.628  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.683  -0.456   0.459  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.503   0.787  -0.333  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.395   1.889   0.199  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.838   0.604  -1.678  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.109   1.309  -0.313  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.118   0.454  -0.235  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.255   0.946  -0.214  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.552   2.282  -0.433  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.888   2.602  -0.390  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.888   1.646  -0.142  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.581   0.310   0.077  1.00  0.00           C  
HETATM   14  N2  UNL     1       4.235  -0.835   0.333  1.00  0.00           N  
HETATM   15  C12 UNL     1       3.331  -1.851   0.448  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.049  -1.307   0.254  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.228   0.022   0.027  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.704  -1.871   0.258  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.404  -0.980  -0.171  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.874  -2.951  -0.648  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.266  -3.365   1.042  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.972  -2.780   0.740  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.072  -0.185   1.464  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.489  -1.047  -0.025  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.270   2.085  -0.440  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.853   2.831   0.381  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.792   1.569   1.204  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.011   1.517  -2.069  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.978   2.359  -0.364  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.831   3.039  -0.625  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.225   3.617  -0.548  1.00  0.00           H  
HETATM   32  H13 UNL     1       4.934   1.923  -0.113  1.00  0.00           H  
HETATM   33  H14 UNL     1       5.261  -0.908   0.423  1.00  0.00           H  
HETATM   34  H15 UNL     1       3.510  -2.896   0.651  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.520  -2.284   1.296  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.763  -2.817  -0.363  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.673  -1.290  -1.226  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   19
CONECT    3    4   23   24
CONECT    4    5    6    7
CONECT    5   25   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

HMDB0033428
     RDKit          3D
(+)-Setoclavine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -1.9026   -2.6811    0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510   -1.2870    0.6285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6829   -0.4561    0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.7873   -0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952    1.8888    0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    0.6043   -1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    1.3089   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178    0.4545   -0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2551    0.9456   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516    2.2822   -0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    2.6021   -0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877    1.6461   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813    0.3101    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -0.8350    0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3305   -1.8514    0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494   -1.3072    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2276    0.0220    0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -1.8713    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -0.9803   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743   -2.9510   -0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2661   -3.3648    1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -2.7798    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0718   -0.1852    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4891   -1.0471   -0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701    2.0846   -0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    2.8313    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919    1.5694    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.5172   -2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781    2.3589   -0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8314    3.0394   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247    3.6175   -0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9344    1.9226   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -0.9082    0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -2.8961    0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203   -2.2844    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629   -2.8173   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.2897   -1.2264 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
  4  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
  5 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
Setoclavine	HMDB

Chemical Formula

C₁₆H₁₈N₂O

Average Molecular Weight

254.3269

Monoisotopic Molecular Weight

254.141913208

IUPAC Name

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-ol

Traditional Name

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-ol

CAS Registry Number

519-12-0

SMILES

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

InChI Identifier

InChI=1S/C16H18N2O/c1-16(19)7-12-11-4-3-5-13-15(11)10(8-17-13)6-14(12)18(2)9-16/h3-5,7-8,14,17,19H,6,9H2,1-2H3

InChI Key

BGVUWLLRNRBDAY-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
Tertiary alcohol
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033428)
Cytoplasm (HMDB: HMDB0033428)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033428)

Source

Exogenous

Exogenous (HMDB: HMDB0033428)

Food

Food (HMDB: HMDB0033428)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0033428)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033428)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	229 - 234 °C	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
Water Solubility	0.69 g/L	ALOGPS
logP	2.46	ALOGPS
logP	1.91	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	7.92	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	0	ChemAxon
Refractivity	77.38 m³·mol⁻¹	ChemAxon
Polarizability	28.96 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
DarkChem	[M+H]+	158.344	31661259
DarkChem	[M-H]-	160.398	31661259
DeepCCS	[M-2H]-	190.874	30932474
DeepCCS	[M+Na]+	166.075	30932474
AllCCS	[M+H]+	159.2	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	162.7	32859911
AllCCS	[M+Na]+	163.7	32859911
AllCCS	[M-H]-	167.2	32859911
AllCCS	[M+Na-2H]-	166.7	32859911
AllCCS	[M+HCOO]-	166.2	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.	3.47 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6848 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.53 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	184.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	605.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	234.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	118.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	80.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	283.6 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	283.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	564.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	690.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	120.6 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	804.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	179.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	450.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	456.9 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	102.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Setoclavine	CN1CC(C)(O)C=C2C1CC1=CNC3=CC=CC2=C13	3917.4	Standard polar	33892256
(+)-Setoclavine	CN1CC(C)(O)C=C2C1CC1=CNC3=CC=CC2=C13	2573.3	Standard non polar	33892256
(+)-Setoclavine	CN1CC(C)(O)C=C2C1CC1=CNC3=CC=CC2=C13	2607.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-Setoclavine,1TMS,isomer #1	CN1CC(C)(O[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2419.3	Semi standard non polar	33892256
(+)-Setoclavine,1TMS,isomer #2	CN1CC(C)(O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2434.7	Semi standard non polar	33892256
(+)-Setoclavine,2TMS,isomer #1	CN1CC(C)(O[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2412.5	Semi standard non polar	33892256
(+)-Setoclavine,2TMS,isomer #1	CN1CC(C)(O[Si](C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)CC21	2561.8	Standard non polar	33892256
(+)-Setoclavine,1TBDMS,isomer #1	CN1CC(C)(O[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=C[NH]4)CC21	2683.2	Semi standard non polar	33892256
(+)-Setoclavine,1TBDMS,isomer #2	CN1CC(C)(O)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	2674.2	Semi standard non polar	33892256
(+)-Setoclavine,2TBDMS,isomer #1	CN1CC(C)(O[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	2873.1	Semi standard non polar	33892256
(+)-Setoclavine,2TBDMS,isomer #1	CN1CC(C)(O[Si](C)(C)C(C)(C)C)C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)CC21	3059.0	Standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB011466

KNApSAcK ID

C00011215

Chemspider ID

8236438

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10060886

PDB ID

Not Available

ChEBI ID

172496

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (+)-Setoclavine (HMDB0033428)

MOL for HMDB0033428 ((+)-Setoclavine)

3D MOL for HMDB0033428 ((+)-Setoclavine)

3D SDF for HMDB0033428 ((+)-Setoclavine)

3D-SDF for HMDB0033428 ((+)-Setoclavine)

PDB for HMDB0033428 ((+)-Setoclavine)

3D PDB for HMDB0033428 ((+)-Setoclavine)

SMILES for HMDB0033428 ((+)-Setoclavine)

INCHI for HMDB0033428 ((+)-Setoclavine)

Structure for HMDB0033428 ((+)-Setoclavine)

3D Structure for HMDB0033428 ((+)-Setoclavine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized