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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:03 UTC

Update Date

2022-03-07 02:52:30 UTC

HMDB ID

HMDB0030312

Secondary Accession Numbers

HMDB30312

Metabolite Identification

Common Name

Floribundine

Description

Floribundine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Floribundine has been detected, but not quantified in, several different foods, such as red tea, green tea, teas (Camellia sinensis), cherimoyas (Annona cherimola), and arabica coffees (Coffea arabica). This could make floribundine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Floribundine.

Structure

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

HMDB0030312
     RDKit          3D
Floribundine
 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.4849    2.1812   -0.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6621    1.7629    0.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    1.5777    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505    2.7370    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.9646    0.7900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8202    2.6878    0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    1.4992    0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    0.3580    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953    0.3976    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4569   -0.8321   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -0.8792    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419   -2.1164    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -3.2273   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396   -3.1928   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -1.9925   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -1.8105   -0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.9871    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -0.9991   -0.1647 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -1.4178    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3212    0.1732   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402    1.4266    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974    1.7913   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    1.6650   -1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5490    3.2656   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344    4.8199    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092    3.5997    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318   -0.0731    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -2.1203    0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3075   -4.1528   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295   -4.0869   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009   -1.1993   -1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0870   -2.7811   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1091   -1.5073    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4331   -1.7701    0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444   -2.2409    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -0.5532    1.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    0.2403   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.0864   -0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302    2.2824   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784    1.4235    1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9  3  1  0
 15 10  1  0
 21  7  1  0
 17  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

  Mrv0541 05061305092D          

 21 24  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 11  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  6  2  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21  2  1  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030312

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO2/c1-19-8-7-12-10-15(20)18(21-2)17-13-6-4-3-5-11(13)9-14(19)16(12)17/h3-6,10,14,20H,7-9H2,1-2H3

> <INCHI_KEY>
AKXOIHNFHOEPHN-UHFFFAOYSA-N

> <FORMULA>
C18H19NO2

> <MOLECULAR_WEIGHT>
281.349

> <EXACT_MASS>
281.141578857

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.316609109736664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
3.240175440333333

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.083928981953455

> <JCHEM_PKA_STRONGEST_BASIC>
10.354868108939904

> <JCHEM_POLAR_SURFACE_AREA>
32.7

> <JCHEM_REFRACTIVITY>
84.47039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030312
     RDKit          3D
Floribundine
 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.4849    2.1812   -0.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6621    1.7629    0.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    1.5777    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505    2.7370    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.9646    0.7900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8202    2.6878    0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    1.4992    0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    0.3580    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953    0.3976    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4569   -0.8321   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -0.8792    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419   -2.1164    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -3.2273   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396   -3.1928   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -1.9925   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -1.8105   -0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.9871    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -0.9991   -0.1647 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -1.4178    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3212    0.1732   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402    1.4266    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974    1.7913   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    1.6650   -1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5490    3.2656   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344    4.8199    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092    3.5997    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318   -0.0731    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -2.1203    0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3075   -4.1528   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295   -4.0869   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009   -1.1993   -1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0870   -2.7811   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1091   -1.5073    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4331   -1.7701    0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444   -2.2409    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -0.5532    1.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    0.2403   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.0864   -0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302    2.2824   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784    1.4235    1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9  3  1  0
 15 10  1  0
 21  7  1  0
 17  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   21                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   19                                                       
CONECT    9   11   14                                                       
CONECT   10   12   15                                                       
CONECT   11    5    9   13                                                  
CONECT   12    7   10   16                                                  
CONECT   13    6   11   17                                                  
CONECT   14    9   16   19                                                  
CONECT   15   10   18   20                                                  
CONECT   16   12   14   17                                                  
CONECT   17   13   16   18                                                  
CONECT   18   15   17   21                                                  
CONECT   19    1    8   14                                                  
CONECT   20   15                                                            
CONECT   21    2   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0030312
HETATM    1  C1  UNL     1      -3.485   2.181  -0.539  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.662   1.763   0.573  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.329   1.578   0.446  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.550   2.737   0.556  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.127   3.965   0.790  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.820   2.688   0.432  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.470   1.499   0.200  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.710   0.358   0.098  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.695   0.398   0.220  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.457  -0.832  -0.077  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.772  -0.879   0.271  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.442  -2.116   0.184  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.770  -3.227  -0.239  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.440  -3.193  -0.594  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.798  -1.993  -0.511  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.596  -1.810  -0.990  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.332  -0.987   0.012  1.00  0.00           C  
HETATM   18  N1  UNL     1       2.745  -0.999  -0.165  1.00  0.00           N  
HETATM   19  C16 UNL     1       3.386  -1.418   1.052  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.321   0.173  -0.725  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.940   1.427   0.048  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.497   1.791  -0.307  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.134   1.665  -1.455  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.549   3.266  -0.615  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.634   4.820   0.877  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.409   3.600   0.517  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.332  -0.073   0.655  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.485  -2.120   0.465  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.307  -4.153  -0.293  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.930  -4.087  -0.925  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.501  -1.199  -1.937  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.087  -2.781  -1.208  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.109  -1.507   1.024  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.433  -1.770   0.877  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.844  -2.241   1.523  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.425  -0.553   1.748  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.038   0.240  -1.786  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.421   0.086  -0.673  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.330   2.282  -0.543  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.478   1.424   1.012  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    7   26
CONECT    7    8   21
CONECT    8    9    9   17
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16
CONECT   16   17   31   32
CONECT   17   18   33
CONECT   18   19   20
CONECT   19   34   35   36
CONECT   20   21   37   38
CONECT   21   39   40
END

HMDB0030312
     RDKit          3D
Floribundine
 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.4849    2.1812   -0.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6621    1.7629    0.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    1.5777    0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505    2.7370    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.9646    0.7900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8202    2.6878    0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    1.4992    0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    0.3580    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953    0.3976    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4569   -0.8321   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -0.8792    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419   -2.1164    0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -3.2273   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396   -3.1928   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981   -1.9925   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -1.8105   -0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.9871    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -0.9991   -0.1647 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -1.4178    1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3212    0.1732   -0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402    1.4266    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4974    1.7913   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    1.6650   -1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5490    3.2656   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344    4.8199    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092    3.5997    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3318   -0.0731    0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -2.1203    0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3075   -4.1528   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295   -4.0869   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009   -1.1993   -1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0870   -2.7811   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1091   -1.5073    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4331   -1.7701    0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8444   -2.2409    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -0.5532    1.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    0.2403   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.0864   -0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302    2.2824   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784    1.4235    1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9  3  1  0
 15 10  1  0
 21  7  1  0
 17  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-N-Methylasimilobine	HMDB
(-)-Nornuciferine	HMDB
1-Methoxy-6a-beta-aporphin-2-ol	HMDB
2-Hydroxy-1-methoxyaporphine	HMDB
N-Methyl-asimilobine	HMDB
N-Methylasimilobine	HMDB
O-Nornuciferine	HMDB

Chemical Formula

C₁₈H₁₉NO₂

Average Molecular Weight

281.349

Monoisotopic Molecular Weight

281.141578857

IUPAC Name

16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol

Traditional Name

16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-15-ol

CAS Registry Number

3153-55-7

SMILES

COC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C23

InChI Identifier

InChI=1S/C18H19NO2/c1-19-8-7-12-10-15(20)18(21-2)17-13-6-4-3-5-11(13)9-14(19)16(12)17/h3-6,10,14,20H,7-9H2,1-2H3

InChI Key

AKXOIHNFHOEPHN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
2-naphthol
Naphthalene
Quinoline
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030312)
Cell membrane (HMDB: HMDB0030312)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030312)

Source

Endogenous

Endogenous (HMDB: HMDB0030312)

Plant

Plant (HMDB: HMDB0030312)
Coffea (HMDB: HMDB0030312)

Exogenous

Food

Food (HMDB: HMDB0030312)

Fruit

Tropical fruit

Cherimoya (FooDB: FOOD00326)

Tea

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0030312)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 - 196 °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	0.17 g/L	ALOGPS
logP	2.87	ALOGPS
logP	3.24	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	10.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.47 m³·mol⁻¹	ChemAxon
Polarizability	31.32 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]+	163.374	31661259
DarkChem	[M-H]-	165.444	31661259
DeepCCS	[M-2H]-	201.366	30932474
DeepCCS	[M+Na]+	176.931	30932474
AllCCS	[M+H]+	165.9	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	169.2	32859911
AllCCS	[M+Na]+	170.2	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	173.5	32859911
AllCCS	[M+HCOO]-	172.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Floribundine	COC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C23	3531.5	Standard polar	33892256
Floribundine	COC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C23	2333.9	Standard non polar	33892256
Floribundine	COC1=C(O)C=C2CCN(C)C3CC4=CC=CC=C4C1=C23	2547.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Floribundine,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C2CCN(C)C3CC4=CC=CC=C4C1=C23	2436.0	Semi standard non polar	33892256
Floribundine,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2CCN(C)C3CC4=CC=CC=C4C1=C23	2664.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Floribundine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-0190000000-20bed70e959559c390af	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Floribundine GC-MS (1 TMS) - 70eV, Positive	splash10-000i-2069000000-51e328f34b3c0e3ddc18	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Floribundine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Floribundine 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 - Floribundine 10V, Positive-QTOF	splash10-001i-0090000000-3a504e770e4ea492389a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 20V, Positive-QTOF	splash10-001i-0090000000-a57a24d36b80b8a0c495	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 40V, Positive-QTOF	splash10-000i-2490000000-c98c65d932127cd8c5b3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 10V, Negative-QTOF	splash10-001i-0090000000-f66a3af6dba71ee6c2f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 20V, Negative-QTOF	splash10-001i-0090000000-47e5b6f6b89143f4e7fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 40V, Negative-QTOF	splash10-08gl-1090000000-4f8f5185a4034c2be047	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 10V, Negative-QTOF	splash10-001i-0090000000-05f98fdd0e260ad54083	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 20V, Negative-QTOF	splash10-001i-0090000000-72c6c81920a1897516b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 40V, Negative-QTOF	splash10-0a4i-0090000000-6cc04a7036ccf3d01639	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 10V, Positive-QTOF	splash10-001i-0090000000-c1fc6cb60e21aea0e16a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 20V, Positive-QTOF	splash10-001i-0090000000-793d4982152e5aba68b8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floribundine 40V, Positive-QTOF	splash10-0hgc-0390000000-c5e4165f365da7c522d2	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002150

KNApSAcK ID

C00025991

Chemspider ID

4477800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319512

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1818901

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 Floribundine (HMDB0030312)

MOL for HMDB0030312 (Floribundine)

3D MOL for HMDB0030312 (Floribundine)

3D SDF for HMDB0030312 (Floribundine)

3D-SDF for HMDB0030312 (Floribundine)

PDB for HMDB0030312 (Floribundine)

3D PDB for HMDB0030312 (Floribundine)

SMILES for HMDB0030312 (Floribundine)

INCHI for HMDB0030312 (Floribundine)

Structure for HMDB0030312 (Floribundine)

3D Structure for HMDB0030312 (Floribundine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra