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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:33 UTC

Update Date

2021-09-14 15:43:53 UTC

HMDB ID

HMDB0060995

Secondary Accession Numbers

HMDB60995

Metabolite Identification

Common Name

10-alpha-methoxy-9,10-dihydrolysergol

Description

10-alpha-methoxy-9,10-dihydrolysergol is a metabolite of nicergoline. Nicergoline (marketed under the trade name Sermion) is an ergot derivative used to treat senile dementia and other disorders with vascular origins. It has been found to increase mental agility and enhance clarity and perception. It decreases vascular resistance and increases arterial blood flow in the brain, improving the utilization of oxygen and glucose by brain cells. It has similar vasoactive properties in other areas of the body, particularly the lungs. (Wikipedia)

Structure

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

HMDB0060995
     RDKit          3D
10-alpha-methoxy-9,10-dihydrolysergol
 43 46  0  0  0  0  0  0  0  0999 V2000
    0.1693    0.6046    2.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552   -0.2879    1.6074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644    0.2135    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691    1.1475   -0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.6083   -0.9147 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6948    1.2338   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194    2.6186   -0.7295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141   -0.8529   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850   -1.6425   -0.3577 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016   -2.9706   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -1.0394   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -2.0621   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1977   -1.3999   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4957   -1.7945   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3140   -0.6963   -0.1922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    0.3911   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7838    1.7712    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    2.6357    0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    2.1939    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    0.8119    0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -0.0307    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295    1.4025    2.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    1.0034    2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.0118    3.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    2.0915   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.4451    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542    0.9641   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8982    1.0868    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4819    0.8880   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    2.9533   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4825   -1.1791   -0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340   -1.2327   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6451   -3.3053   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9347   -3.7104   -0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4083   -3.0030   -1.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -0.7651   -1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -2.3656    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -2.8822   -0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -2.8256   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3564   -0.6837   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059    2.0932    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9576    3.6871    0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    2.8724    0.4781 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
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11  3  1  0
 21 13  1  0
 20  3  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
M  END


  Mrv0541 07091309112D          

 21 24  0  0  0  0            999 V2000
   -2.2700   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5885   -2.6306    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
   -0.1281   -2.2187    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
   -1.5570   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.6304    0.0000 C   0  0  2  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
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -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
   -0.1271   -1.3937    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
   -1.5560   -1.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -3.8687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5877   -1.8056    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
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  1  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  4  1  0  0  0  0
 14  5  2  0  0  0  0
 15  6  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17  7  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18  8  1  0  0  0  0
 18 14  1  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  0  0  0  0
 19 15  1  0  0  0  0
 20 10  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060995

> <DATABASE_NAME>
hmdb

> <SMILES>
COC12C[C@@H](CO)CN(C)C1CC1=CNC3=CC=CC2=C13

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O2/c1-19-9-11(10-20)7-17(21-2)13-4-3-5-14-16(13)12(8-18-14)6-15(17)19/h3-5,8,11,15,18,20H,6-7,9-10H2,1-2H3/t11-,15?,17?/m1/s1

> <INCHI_KEY>
JGQZSBLQHCTAJF-NFXPUDJFSA-N

> <FORMULA>
C17H22N2O2

> <MOLECULAR_WEIGHT>
286.3688

> <EXACT_MASS>
286.168127958

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.195708921239074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.4252688310000012

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.973431682795784

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.413270510473946

> <JCHEM_PKA_STRONGEST_BASIC>
8.16125923967615

> <JCHEM_POLAR_SURFACE_AREA>
48.49000000000001

> <JCHEM_REFRACTIVITY>
83.11280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-2-methoxy-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060995
     RDKit          3D
10-alpha-methoxy-9,10-dihydrolysergol
 43 46  0  0  0  0  0  0  0  0999 V2000
    0.1693    0.6046    2.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552   -0.2879    1.6074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644    0.2135    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691    1.1475   -0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.6083   -0.9147 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6948    1.2338   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194    2.6186   -0.7295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141   -0.8529   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850   -1.6425   -0.3577 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016   -2.9706   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -1.0394   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -2.0621   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1977   -1.3999   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4957   -1.7945   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3140   -0.6963   -0.1922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    0.3911   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7838    1.7712    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    2.6357    0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    2.1939    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    0.8119    0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -0.0307    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295    1.4025    2.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    1.0034    2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.0118    3.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    2.0915   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.4451    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542    0.9641   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8982    1.0868    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4819    0.8880   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    2.9533   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4825   -1.1791   -0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340   -1.2327   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6451   -3.3053   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9347   -3.7104   -0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4083   -3.0030   -1.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -0.7651   -1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -2.3656    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -2.8822   -0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -2.8256   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3564   -0.6837   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059    2.0932    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9576    3.6871    0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    2.8724    0.4781 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
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11  3  1  0
 21 13  1  0
 20  3  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      -4.237  -1.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.099  -4.910   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      -0.239  -4.142   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      -2.906  -4.138   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.575  -6.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.574  -4.910   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.237  -2.602   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -2.905  -2.598   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -0.243  -7.222   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.097  -3.370   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   21                                                            
CONECT    3    4    5                                                       
CONECT    4    3   13                                                       
CONECT    5    3   14                                                       
CONECT    6   12   15                                                       
CONECT    7   11   17                                                       
CONECT    8   12   18                                                       
CONECT    9   11   19                                                       
CONECT   10   11   20                                                       
CONECT   11    7    9   10                                                  
CONECT   12    6    8   16                                                  
CONECT   13    4   16   17                                                  
CONECT   14    5   16   18                                                  
CONECT   15    6   17   19                                                  
CONECT   16   12   13   14                                                  
CONECT   17    7   13   15   21                                             
CONECT   18    8   14                                                       
CONECT   19    1    9   15                                                  
CONECT   20   10                                                            
CONECT   21    2   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0060995
HETATM    1  C1  UNL     1       0.169   0.605   2.625  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.255  -0.288   1.607  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.164   0.214   0.311  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.269   1.147  -0.005  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.336   0.608  -0.915  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.695   1.234  -0.553  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.519   2.619  -0.730  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.514  -0.853  -0.954  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.485  -1.643  -0.358  1.00  0.00           N  
HETATM   10  C7  UNL     1       1.602  -2.971  -0.862  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.188  -1.039  -0.559  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.840  -2.062  -0.026  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.198  -1.400  -0.071  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.496  -1.794  -0.220  1.00  0.00           C  
HETATM   15  N2  UNL     1      -4.314  -0.696  -0.192  1.00  0.00           N  
HETATM   16  C12 UNL     1      -3.561   0.391  -0.027  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.784   1.771   0.083  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.712   2.636   0.259  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.412   2.194   0.334  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.186   0.812   0.224  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.257  -0.031   0.049  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.930   1.403   2.674  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.863   1.003   2.795  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.358   0.012   3.574  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.919   2.092  -0.467  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.790   1.445   0.919  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.154   0.964  -1.971  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.898   1.087   0.526  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.482   0.888  -1.221  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.827   2.953  -0.128  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.482  -1.179  -0.466  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.634  -1.233  -2.013  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.645  -3.305  -0.695  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.935  -3.710  -0.406  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.408  -3.003  -1.973  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.042  -0.765  -1.591  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.559  -2.366   0.981  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.894  -2.882  -0.770  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.815  -2.826  -0.342  1.00  0.00           H  
HETATM   40  H19 UNL     1      -5.356  -0.684  -0.283  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.806   2.093   0.021  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.958   3.687   0.336  1.00  0.00           H  
HETATM   43  H22 UNL     1      -0.608   2.872   0.478  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4   11   20
CONECT    4    5   25   26
CONECT    5    6    8   27
CONECT    6    7   28   29
CONECT    7   30
CONECT    8    9   31   32
CONECT    9   10   11
CONECT   10   33   34   35
CONECT   11   12   36
CONECT   12   13   37   38
CONECT   13   14   14   21
CONECT   14   15   39
CONECT   15   16   40
CONECT   16   17   17   21
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   43
CONECT   20   21   21
END

HMDB0060995
     RDKit          3D
10-alpha-methoxy-9,10-dihydrolysergol
 43 46  0  0  0  0  0  0  0  0999 V2000
    0.1693    0.6046    2.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552   -0.2879    1.6074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644    0.2135    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691    1.1475   -0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.6083   -0.9147 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6948    1.2338   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194    2.6186   -0.7295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141   -0.8529   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850   -1.6425   -0.3577 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016   -2.9706   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -1.0394   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -2.0621   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1977   -1.3999   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4957   -1.7945   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3140   -0.6963   -0.1922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    0.3911   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7838    1.7712    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    2.6357    0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123    2.1939    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    0.8119    0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -0.0307    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295    1.4025    2.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    1.0034    2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.0118    3.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191    2.0915   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    1.4451    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542    0.9641   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8982    1.0868    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4819    0.8880   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    2.9533   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4825   -1.1791   -0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340   -1.2327   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6451   -3.3053   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9347   -3.7104   -0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4083   -3.0030   -1.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -0.7651   -1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -2.3656    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -2.8822   -0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -2.8256   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3564   -0.6837   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059    2.0932    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9576    3.6871    0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    2.8724    0.4781 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
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11  3  1  0
 21 13  1  0
 20  3  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-a-Methoxy-9,10-dihydrolysergol	Generator
10-Α-methoxy-9,10-dihydrolysergol	Generator

Chemical Formula

C₁₇H₂₂N₂O₂

Average Molecular Weight

286.3688

Monoisotopic Molecular Weight

286.168127958

IUPAC Name

[(4R)-2-methoxy-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol

Traditional Name

[(4R)-2-methoxy-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol

CAS Registry Number

Not Available

SMILES

COC12C[C@@H](CO)CN(C)C1CC1=CNC3=CC=CC2=C13

InChI Identifier

InChI=1S/C17H22N2O2/c1-19-9-11(10-20)7-17(21-2)13-4-3-5-14-16(13)12(8-18-14)6-15(17)19/h3-5,8,11,15,18,20H,6-7,9-10H2,1-2H3/t11-,15?,17?/m1/s1

InChI Key

JGQZSBLQHCTAJF-NFXPUDJFSA-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
Isoindole or derivatives
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
1,3-aminoalcohol
Heteroaromatic compound
Pyrrole
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060995)
Liver (HMDB: HMDB0060995)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060995)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060995)

Cellular substructure

Cytoplasm (HMDB: HMDB0060995)

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
Water Solubility	0.89 g/L	ALOGPS
logP	2.15	ALOGPS
logP	1.43	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	8.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.11 m³·mol⁻¹	ChemAxon
Polarizability	32.2 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
DarkChem	[M+H]+	165.599	31661259
DarkChem	[M-H]-	162.676	31661259
DeepCCS	[M-2H]-	197.638	30932474
DeepCCS	[M+Na]+	172.717	30932474
AllCCS	[M+H]+	168.1	32859911
AllCCS	[M+H-H2O]+	164.6	32859911
AllCCS	[M+NH4]+	171.3	32859911
AllCCS	[M+Na]+	172.2	32859911
AllCCS	[M-H]-	174.7	32859911
AllCCS	[M+Na-2H]-	174.5	32859911
AllCCS	[M+HCOO]-	174.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
10-alpha-methoxy-9,10-dihydrolysergol	COC12C[C@@H](CO)CN(C)C1CC1=CNC3=CC=CC2=C13	3968.1	Standard polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol	COC12C[C@@H](CO)CN(C)C1CC1=CNC3=CC=CC2=C13	2515.9	Standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol	COC12C[C@@H](CO)CN(C)C1CC1=CNC3=CC=CC2=C13	2765.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
10-alpha-methoxy-9,10-dihydrolysergol,1TMS,isomer #1	COC12C[C@@H](CO[Si](C)(C)C)CN(C)C1CC1=C[NH]C3=CC=CC2=C13	2523.7	Semi standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,1TMS,isomer #2	COC12C[C@@H](CO)CN(C)C1CC1=CN([Si](C)(C)C)C3=CC=CC2=C13	2528.4	Semi standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,2TMS,isomer #1	COC12C[C@@H](CO[Si](C)(C)C)CN(C)C1CC1=CN([Si](C)(C)C)C3=CC=CC2=C13	2525.5	Semi standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,2TMS,isomer #1	COC12C[C@@H](CO[Si](C)(C)C)CN(C)C1CC1=CN([Si](C)(C)C)C3=CC=CC2=C13	2698.8	Standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,2TMS,isomer #1	COC12C[C@@H](CO[Si](C)(C)C)CN(C)C1CC1=CN([Si](C)(C)C)C3=CC=CC2=C13	2970.9	Standard polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,1TBDMS,isomer #1	COC12C[C@@H](CO[Si](C)(C)C(C)(C)C)CN(C)C1CC1=C[NH]C3=CC=CC2=C13	2769.6	Semi standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,1TBDMS,isomer #2	COC12C[C@@H](CO)CN(C)C1CC1=CN([Si](C)(C)C(C)(C)C)C3=CC=CC2=C13	2759.8	Semi standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,2TBDMS,isomer #1	COC12C[C@@H](CO[Si](C)(C)C(C)(C)C)CN(C)C1CC1=CN([Si](C)(C)C(C)(C)C)C3=CC=CC2=C13	2950.1	Semi standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,2TBDMS,isomer #1	COC12C[C@@H](CO[Si](C)(C)C(C)(C)C)CN(C)C1CC1=CN([Si](C)(C)C(C)(C)C)C3=CC=CC2=C13	3178.4	Standard non polar	33892256
10-alpha-methoxy-9,10-dihydrolysergol,2TBDMS,isomer #1	COC12C[C@@H](CO[Si](C)(C)C(C)(C)C)CN(C)C1CC1=CN([Si](C)(C)C(C)(C)C)C3=CC=CC2=C13	3187.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004s-1950000000-d8367098f8214f599e0a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol GC-MS (1 TMS) - 70eV, Positive	splash10-005a-3961000000-b461d735b6724f466171	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 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 - 10-alpha-methoxy-9,10-dihydrolysergol 10V, Positive-QTOF	splash10-00kr-0090000000-717fd2849930b4428a64	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 20V, Positive-QTOF	splash10-014r-0090000000-4510b13bf0fa192a4142	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 40V, Positive-QTOF	splash10-0abc-9270000000-979a002d5a3a0c2c2cad	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 10V, Negative-QTOF	splash10-000i-0090000000-46330b9fd6abedc135a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 20V, Negative-QTOF	splash10-052r-0090000000-423065c9eabcd800e842	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 40V, Negative-QTOF	splash10-001c-8590000000-c98f52224a3d98e1df0f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 10V, Positive-QTOF	splash10-0a4r-0090000000-b18d3076b3ebd0d8c527	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 20V, Positive-QTOF	splash10-0a70-0090000000-16c151483e6b45e7b824	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 40V, Positive-QTOF	splash10-005i-0690000000-789cd40191eeb7b500d0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 10V, Negative-QTOF	splash10-000i-0090000000-0d7d146f1c8899c10901	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 20V, Negative-QTOF	splash10-000i-0090000000-c4c238bf50fb2fae7aac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-alpha-methoxy-9,10-dihydrolysergol 40V, Negative-QTOF	splash10-001i-0290000000-bc755664ce120ab78f03	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

35031828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107927

PDB ID

Not Available

ChEBI ID

178696

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

Not Available

Showing metabocard for 10-alpha-methoxy-9,10-dihydrolysergol (HMDB0060995)

MOL for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

3D MOL for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

3D SDF for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

3D-SDF for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

PDB for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

3D PDB for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

SMILES for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

INCHI for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

Structure for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

3D Structure for HMDB0060995 (10-alpha-methoxy-9,10-dihydrolysergol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra