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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:25 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030201

Secondary Accession Numbers

HMDB30201

Metabolite Identification

Common Name

(-)-Fumigaclavine B

Description

(-)-Fumigaclavine B, also known as N-demethylfrangulanine, 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. Based on a literature review a significant number of articles have been published on (-)-Fumigaclavine B.

Structure

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

HMDB0030201
     RDKit          3D
(-)-Fumigaclavine B
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.6330    1.6856   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.8461   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6058   -0.5225   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396   -1.3656   -0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8627   -2.7310   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -0.9198   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9347    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738   -1.4663    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266   -2.0312    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621   -1.0373    0.2155 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    0.1448    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203    1.4716    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585    2.4611    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001    2.1692    0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    0.8433    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.1107    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042    0.4158    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    1.4567   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3280    2.3926    0.6697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3191    2.6404    0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498    1.1555    0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    1.9050   -1.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    0.7072   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4408   -0.4269    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152   -0.9185   -0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.9357   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6751   -2.8820    0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370   -3.4649   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061   -0.7882   -1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -2.8640   -0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533   -2.0519    1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -3.0963    0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2102   -1.1489    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776    1.7078    0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059    3.4882    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    2.9377    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4474    0.2769    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133    2.0097   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252    1.9814    1.5532 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18  2  1  0
 17  6  1  0
 16  8  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv0541 05061305042D          

 19 22  0  0  0  0            999 V2000
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.9786    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
    0.1714    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
   -0.8430   -2.6304    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
    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
   -0.1281   -2.2187    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
    0.5859   -2.6321    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
  9  1  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17  7  1  0  0  0  0
 17 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  1  0  0  0  0
 18 13  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030201

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CN(C)C2CC3=CNC4=CC=CC(C2C1O)=C34

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O/c1-9-8-18(2)13-6-10-7-17-12-5-3-4-11(14(10)12)15(13)16(9)19/h3-5,7,9,13,15-17,19H,6,8H2,1-2H3

> <INCHI_KEY>
JUXRVSRUBIFVKE-UHFFFAOYSA-N

> <FORMULA>
C16H20N2O

> <MOLECULAR_WEIGHT>
256.3428

> <EXACT_MASS>
256.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.673356284377952

> <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),9,12,14-tetraen-3-ol

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
1.7990977190000013

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.353600687696055

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.476082558027883

> <JCHEM_PKA_STRONGEST_BASIC>
8.460818280721714

> <JCHEM_POLAR_SURFACE_AREA>
39.260000000000005

> <JCHEM_REFRACTIVITY>
76.7065

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030201
     RDKit          3D
(-)-Fumigaclavine B
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.6330    1.6856   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.8461   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6058   -0.5225   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396   -1.3656   -0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8627   -2.7310   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -0.9198   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9347    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738   -1.4663    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266   -2.0312    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621   -1.0373    0.2155 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    0.1448    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203    1.4716    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585    2.4611    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001    2.1692    0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    0.8433    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.1107    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042    0.4158    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    1.4567   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3280    2.3926    0.6697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3191    2.6404    0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498    1.1555    0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    1.9050   -1.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    0.7072   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4408   -0.4269    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152   -0.9185   -0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.9357   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6751   -2.8820    0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370   -3.4649   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061   -0.7882   -1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -2.8640   -0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533   -2.0519    1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -3.0963    0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2102   -1.1489    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776    1.7078    0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059    3.4882    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    2.9377    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4474    0.2769    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133    2.0097   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252    1.9814    1.5532 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18  2  1  0
 17  6  1  0
 16  8  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  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      -1.575  -6.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.237  -1.827   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       0.320   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.906  -4.138   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.574  -4.910   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       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.237  -2.602   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.239  -4.142   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      -2.905  -2.598   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       1.094  -4.913   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   18                                                            
CONECT    3    4    5                                                       
CONECT    4    3   11                                                       
CONECT    5    3   12                                                       
CONECT    6   10   13                                                       
CONECT    7   10   17                                                       
CONECT    8    9   18                                                       
CONECT    9    1    8   16                                                  
CONECT   10    6    7   14                                                  
CONECT   11    4   14   15                                                  
CONECT   12    5   14   17                                                  
CONECT   13    6   15   18                                                  
CONECT   14   10   11   12                                                  
CONECT   15   11   13   16                                                  
CONECT   16    9   15   19                                                  
CONECT   17    7   12                                                       
CONECT   18    2    8   13                                                  
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0030201
HETATM    1  C1  UNL     1      -3.633   1.686  -0.180  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.475   0.846  -0.646  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.606  -0.523  -0.002  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.640  -1.366  -0.636  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.863  -2.731  -0.278  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.297  -0.920  -0.535  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.555  -1.935   0.212  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.974  -1.466   0.216  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.227  -2.031   0.240  1.00  0.00           C  
HETATM   10  N2  UNL     1       4.162  -1.037   0.215  1.00  0.00           N  
HETATM   11  C9  UNL     1       3.525   0.145   0.176  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.920   1.472   0.136  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.958   2.461   0.099  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.600   2.169   0.101  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.209   0.843   0.141  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.175  -0.111   0.176  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.204   0.416   0.158  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.140   1.457  -0.356  1.00  0.00           C  
HETATM   19  O1  UNL     1      -1.328   2.393   0.670  1.00  0.00           O  
HETATM   20  H1  UNL     1      -3.319   2.640   0.274  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.250   1.155   0.585  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.332   1.905  -1.030  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.560   0.707  -1.743  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.441  -0.427   1.090  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.615  -0.919  -0.223  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.956  -2.936  -0.418  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.675  -2.882   0.815  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.337  -3.465  -0.909  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.206  -0.788  -1.536  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.543  -2.864  -0.394  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.153  -2.052   1.218  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.408  -3.096   0.274  1.00  0.00           H  
HETATM   33  H14 UNL     1       5.210  -1.149   0.225  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.978   1.708   0.134  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.306   3.488   0.068  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.848   2.938   0.071  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.447   0.277   1.253  1.00  0.00           H  
HETATM   38  H19 UNL     1      -0.713   2.010  -1.215  1.00  0.00           H  
HETATM   39  H20 UNL     1      -1.125   1.981   1.553  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   18   23
CONECT    3    4   24   25
CONECT    4    5    6
CONECT    5   26   27   28
CONECT    6    7   17   29
CONECT    7    8   30   31
CONECT    8    9    9   16
CONECT    9   10   32
CONECT   10   11   33
CONECT   11   12   12   16
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   16   17
CONECT   17   18   37
CONECT   18   19   38
CONECT   19   39
END

HMDB0030201
     RDKit          3D
(-)-Fumigaclavine B
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.6330    1.6856   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.8461   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6058   -0.5225   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396   -1.3656   -0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8627   -2.7310   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -0.9198   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9347    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738   -1.4663    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266   -2.0312    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621   -1.0373    0.2155 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    0.1448    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203    1.4716    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585    2.4611    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001    2.1692    0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    0.8433    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749   -0.1107    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042    0.4158    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    1.4567   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3280    2.3926    0.6697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3191    2.6404    0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498    1.1555    0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    1.9050   -1.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    0.7072   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4408   -0.4269    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152   -0.9185   -0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.9357   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6751   -2.8820    0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370   -3.4649   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061   -0.7882   -1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -2.8640   -0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533   -2.0519    1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -3.0963    0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2102   -1.1489    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776    1.7078    0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059    3.4882    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    2.9377    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4474    0.2769    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133    2.0097   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252    1.9814    1.5532 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18  2  1  0
 17  6  1  0
 16  8  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Demethylfrangulanine	HMDB
Fumigaclavine b	HMDB
6,8-Dimethylergolin-9-ol	HMDB
Isofumigaclavine b	HMDB

Chemical Formula

C₁₆H₂₀N₂O

Average Molecular Weight

256.3428

Monoisotopic Molecular Weight

256.157563272

IUPAC Name

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-ol

Traditional Name

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-ol

CAS Registry Number

6879-93-2

SMILES

CC1CN(C)C2CC3=CNC4=CC=CC(C2C1O)=C34

InChI Identifier

InChI=1S/C16H20N2O/c1-9-8-18(2)13-6-10-7-17-12-5-3-4-11(14(10)12)15(13)16(9)19/h3-5,7,9,13,15-17,19H,6,8H2,1-2H3

InChI Key

JUXRVSRUBIFVKE-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
Piperidine
Pyrrole
Heteroaromatic compound
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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: HMDB0030201)
Cytoplasm (HMDB: HMDB0030201)

Source

Endogenous

Endogenous (HMDB: HMDB0030201)

Exogenous

Food

Food (HMDB: HMDB0030201)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	265 - 267 °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	1.47 g/L	ALOGPS
logP	2.38	ALOGPS
logP	1.8	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	8.46	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	76.71 m³·mol⁻¹	ChemAxon
Polarizability	28.67 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]+	160.034	31661259
DarkChem	[M-H]-	159.193	31661259
DeepCCS	[M-2H]-	192.155	30932474
DeepCCS	[M+Na]+	167.72	30932474
AllCCS	[M+H]+	161.0	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	164.5	32859911
AllCCS	[M+Na]+	165.5	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Fumigaclavine B	CC1CN(C)C2CC3=CNC4=CC=CC(C2C1O)=C34	3703.9	Standard polar	33892256
(-)-Fumigaclavine B	CC1CN(C)C2CC3=CNC4=CC=CC(C2C1O)=C34	2508.0	Standard non polar	33892256
(-)-Fumigaclavine B	CC1CN(C)C2CC3=CNC4=CC=CC(C2C1O)=C34	2625.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Fumigaclavine B,1TMS,isomer #1	CC1CN(C)C2CC3=C[NH]C4=CC=CC(=C34)C2C1O[Si](C)(C)C	2441.4	Semi standard non polar	33892256
(-)-Fumigaclavine B,1TMS,isomer #2	CC1CN(C)C2CC3=CN([Si](C)(C)C)C4=CC=CC(=C34)C2C1O	2472.9	Semi standard non polar	33892256
(-)-Fumigaclavine B,2TMS,isomer #1	CC1CN(C)C2CC3=CN([Si](C)(C)C)C4=CC=CC(=C34)C2C1O[Si](C)(C)C	2411.8	Semi standard non polar	33892256
(-)-Fumigaclavine B,2TMS,isomer #1	CC1CN(C)C2CC3=CN([Si](C)(C)C)C4=CC=CC(=C34)C2C1O[Si](C)(C)C	2490.0	Standard non polar	33892256
(-)-Fumigaclavine B,1TBDMS,isomer #1	CC1CN(C)C2CC3=C[NH]C4=CC=CC(=C34)C2C1O[Si](C)(C)C(C)(C)C	2668.0	Semi standard non polar	33892256
(-)-Fumigaclavine B,1TBDMS,isomer #2	CC1CN(C)C2CC3=CN([Si](C)(C)C(C)(C)C)C4=CC=CC(=C34)C2C1O	2702.4	Semi standard non polar	33892256
(-)-Fumigaclavine B,2TBDMS,isomer #1	CC1CN(C)C2CC3=CN([Si](C)(C)C(C)(C)C)C4=CC=CC(=C34)C2C1O[Si](C)(C)C(C)(C)C	2804.7	Semi standard non polar	33892256
(-)-Fumigaclavine B,2TBDMS,isomer #1	CC1CN(C)C2CC3=CN([Si](C)(C)C(C)(C)C)C4=CC=CC(=C34)C2C1O[Si](C)(C)C(C)(C)C	2992.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Fumigaclavine B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1920000000-81fed3643e2843d2b1f1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Fumigaclavine B GC-MS (1 TMS) - 70eV, Positive	splash10-006t-7963000000-2c120c45120ede6301af	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Fumigaclavine B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Fumigaclavine B 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 - (-)-Fumigaclavine B 10V, Negative-QTOF	splash10-0a4i-0090000000-1b660ecea89bd9325ef5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 20V, Negative-QTOF	splash10-0a4i-1290000000-d07330c7897fca721935	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 40V, Negative-QTOF	splash10-0udi-3900000000-1a8188063faf0b18fcb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 10V, Negative-QTOF	splash10-0a4i-0090000000-ca82db7f0f7f6291e478	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 20V, Negative-QTOF	splash10-0a4i-0090000000-ef72f227b8673d1b10e5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 40V, Negative-QTOF	splash10-004r-0890000000-c960f8bbaaa20800cc46	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 10V, Positive-QTOF	splash10-052r-0090000000-d859a3cf6e1c9345396e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 20V, Positive-QTOF	splash10-052r-0390000000-13481dda933b6e9ac3d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 40V, Positive-QTOF	splash10-0ufr-0900000000-b35006c40391c11a8811	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 10V, Positive-QTOF	splash10-0a4r-0090000000-97d8d65a48f025f64a37	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 20V, Positive-QTOF	splash10-0a4i-0090000000-d7017d8926ef3a2cac18	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Fumigaclavine B 40V, Positive-QTOF	splash10-03ni-0940000000-00b87fbb8c4f9f1015a0	2021-09-24	Wishart Lab	View Spectrum

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

FDB002019

KNApSAcK ID

C00011248

Chemspider ID

35013159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318090

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

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

Showing metabocard for (-)-Fumigaclavine B (HMDB0030201)

MOL for HMDB0030201 ((-)-Fumigaclavine B)

3D MOL for HMDB0030201 ((-)-Fumigaclavine B)

3D SDF for HMDB0030201 ((-)-Fumigaclavine B)

3D-SDF for HMDB0030201 ((-)-Fumigaclavine B)

PDB for HMDB0030201 ((-)-Fumigaclavine B)

3D PDB for HMDB0030201 ((-)-Fumigaclavine B)

SMILES for HMDB0030201 ((-)-Fumigaclavine B)

INCHI for HMDB0030201 ((-)-Fumigaclavine B)

Structure for HMDB0030201 ((-)-Fumigaclavine B)

3D Structure for HMDB0030201 ((-)-Fumigaclavine B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra