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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:29:47 UTC

Update Date

2022-03-07 02:53:50 UTC

HMDB ID

HMDB0033737

Secondary Accession Numbers

HMDB33737

Metabolite Identification

Common Name

Dehydronuciferine

Description

Dehydronuciferine 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. Dehydronuciferine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make dehydronuciferine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydronuciferine.

Structure

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

HMDB0033737
     RDKit          3D
Dehydronuciferine
 41 44  0  0  0  0  0  0  0  0999 V2000
    3.2789   -3.4878    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0230   -2.1197    0.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7696   -1.5709    0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6487   -2.3201    0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799   -1.7548    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6504   -0.3781    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    0.2053   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    1.5594   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8825    2.3520   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336    3.7239   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0200    4.5518    0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2527    4.0041    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4499    2.6180    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    1.8129    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999    0.4276    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986   -0.1697    0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883    0.5118    0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    0.6395   -0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -0.6403   -0.4013 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555   -0.0490   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439   -2.0040    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045   -2.6855   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0434   -3.9307    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3624   -3.6655    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700   -4.0010    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.3974    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9683    1.9880   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161    4.1172   -0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684    5.6154    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750    4.6783    0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4173    2.3155    0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    0.6911   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794    1.5312   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4016   -0.2456   -0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9430   -0.8075   -1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8748    0.3556   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5989    0.7609   -0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3623   -2.0466    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012   -2.5863   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -3.4998    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -3.0992   -1.1707 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 16  3  1  0
 22  5  1  0
 15  6  1  0
 14  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END


  Mrv0541 05061307192D          

 22 25  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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 12  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  2  0  0  0  0
 14 12  1  0  0  0  0
 15 10  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20  1  1  0  0  0  0
 20  9  1  0  0  0  0
 20 15  1  0  0  0  0
 21  2  1  0  0  0  0
 21 16  1  0  0  0  0
 22  3  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033737

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,10-11H,8-9H2,1-3H3

> <INCHI_KEY>
JBGSWIBJAGBGOP-UHFFFAOYSA-N

> <FORMULA>
C19H19NO2

> <MOLECULAR_WEIGHT>
293.3597

> <EXACT_MASS>
293.141578857

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.1134306872732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
3.7847891629999992

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.721520503316351

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
89.62299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033737
     RDKit          3D
Dehydronuciferine
 41 44  0  0  0  0  0  0  0  0999 V2000
    3.2789   -3.4878    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0230   -2.1197    0.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7696   -1.5709    0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6487   -2.3201    0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799   -1.7548    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6504   -0.3781    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    0.2053   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    1.5594   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8825    2.3520   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336    3.7239   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0200    4.5518    0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2527    4.0041    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4499    2.6180    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    1.8129    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999    0.4276    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986   -0.1697    0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883    0.5118    0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    0.6395   -0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -0.6403   -0.4013 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555   -0.0490   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439   -2.0040    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045   -2.6855   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0434   -3.9307    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3624   -3.6655    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700   -4.0010    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.3974    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9683    1.9880   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161    4.1172   -0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684    5.6154    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750    4.6783    0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4173    2.3155    0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    0.6911   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794    1.5312   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4016   -0.2456   -0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9430   -0.8075   -1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8748    0.3556   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5989    0.7609   -0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3623   -2.0466    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012   -2.5863   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -3.4998    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -3.0992   -1.1707 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 16  3  1  0
 22  5  1  0
 15  6  1  0
 14  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   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   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   14                                                       
CONECT    8    9   13                                                       
CONECT    9    8   20                                                       
CONECT   10   12   15                                                       
CONECT   11   13   16                                                       
CONECT   12    6   10   14                                                  
CONECT   13    8   11   17                                                  
CONECT   14    7   12   18                                                  
CONECT   15   10   17   20                                                  
CONECT   16   11   19   21                                                  
CONECT   17   13   15   18                                                  
CONECT   18   14   17   19                                                  
CONECT   19   16   18   22                                                  
CONECT   20    1    9   15                                                  
CONECT   21    2   16                                                       
CONECT   22    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0033737
HETATM    1  C1  UNL     1       3.279  -3.488   0.789  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.023  -2.120   0.724  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.770  -1.571   0.488  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.649  -2.320   0.294  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.580  -1.755   0.063  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.650  -0.378   0.034  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.868   0.205  -0.192  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.982   1.559  -0.219  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.883   2.352  -0.018  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.034   3.724  -0.006  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.020   4.552   0.233  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.253   4.004   0.467  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.450   2.618   0.463  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.373   1.813   0.215  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.500   0.428   0.236  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.699  -0.170   0.456  1.00  0.00           C  
HETATM   17  O2  UNL     1       2.888   0.512   0.648  1.00  0.00           O  
HETATM   18  C16 UNL     1       3.759   0.639  -0.529  1.00  0.00           C  
HETATM   19  N1  UNL     1      -3.001  -0.640  -0.401  1.00  0.00           N  
HETATM   20  C17 UNL     1      -4.155  -0.049  -1.070  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.044  -2.004   0.008  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.704  -2.686  -0.129  1.00  0.00           C  
HETATM   23  H1  UNL     1       3.043  -3.931   1.797  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.362  -3.666   0.569  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.670  -4.001   0.019  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.746  -3.397   0.327  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.968   1.988  -0.405  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.016   4.117  -0.193  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.168   5.615   0.227  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.075   4.678   0.656  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.417   2.315   0.705  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.118   0.691  -1.417  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.379   1.531  -0.452  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.402  -0.246  -0.601  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.943  -0.808  -1.246  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.875   0.356  -2.064  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.599   0.761  -0.421  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.362  -2.047   1.070  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.801  -2.586  -0.560  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.606  -3.500   0.607  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.635  -3.099  -1.171  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   26
CONECT    5    6    6   22
CONECT    6    7   15
CONECT    7    8    8   19
CONECT    8    9   27
CONECT    9   10   10   14
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15
CONECT   15   16   16
CONECT   16   17
CONECT   17   18
CONECT   18   32   33   34
CONECT   19   20   21
CONECT   20   35   36   37
CONECT   21   22   38   39
CONECT   22   40   41
END

HMDB0033737
     RDKit          3D
Dehydronuciferine
 41 44  0  0  0  0  0  0  0  0999 V2000
    3.2789   -3.4878    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0230   -2.1197    0.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7696   -1.5709    0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6487   -2.3201    0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799   -1.7548    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6504   -0.3781    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    0.2053   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    1.5594   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8825    2.3520   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336    3.7239   -0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0200    4.5518    0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2527    4.0041    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4499    2.6180    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    1.8129    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999    0.4276    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986   -0.1697    0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883    0.5118    0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592    0.6395   -0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005   -0.6403   -0.4013 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555   -0.0490   -1.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439   -2.0040    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045   -2.6855   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0434   -3.9307    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3624   -3.6655    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700   -4.0010    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.3974    0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9683    1.9880   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161    4.1172   -0.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684    5.6154    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750    4.6783    0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4173    2.3155    0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    0.6911   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794    1.5312   -0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4016   -0.2456   -0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9430   -0.8075   -1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8748    0.3556   -2.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5989    0.7609   -0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3623   -2.0466    1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012   -2.5863   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6061   -3.4998    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -3.0992   -1.1707 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
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 16  3  1  0
 22  5  1  0
 15  6  1  0
 14  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
L-cis-4-(Hydroxymethyl)-2-pyrrolidinecarboxylate	HMDB

Chemical Formula

C₁₉H₁₉NO₂

Average Molecular Weight

293.3597

Monoisotopic Molecular Weight

293.141578857

IUPAC Name

15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene

Traditional Name

15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene

CAS Registry Number

7630-74-2

SMILES

COC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C1

InChI Identifier

InChI=1S/C19H19NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,10-11H,8-9H2,1-3H3

InChI Key

JBGSWIBJAGBGOP-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
Naphthalene
Quinoline
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033737)

Cellular substructure

Membrane (HMDB: HMDB0033737)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033737)

Source

Exogenous

Food

Food (HMDB: HMDB0033737)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0033737)

Not Available

Nutrient (HMDB: HMDB0033737)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	130 - 131 °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	0.0069 g/L	ALOGPS
logP	4.46	ALOGPS
logP	3.78	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	4.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.62 m³·mol⁻¹	ChemAxon
Polarizability	33.11 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]+	168.772	31661259
DarkChem	[M-H]-	170.827	31661259
DeepCCS	[M-2H]-	211.497	30932474
DeepCCS	[M+Na]+	186.805	30932474
AllCCS	[M+H]+	167.7	32859911
AllCCS	[M+H-H2O]+	164.1	32859911
AllCCS	[M+NH4]+	171.1	32859911
AllCCS	[M+Na]+	172.1	32859911
AllCCS	[M-H]-	177.4	32859911
AllCCS	[M+Na-2H]-	176.5	32859911
AllCCS	[M+HCOO]-	175.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydronuciferine	COC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C1	3612.0	Standard polar	33892256
Dehydronuciferine	COC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C1	2494.8	Standard non polar	33892256
Dehydronuciferine	COC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C1	2891.4	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 - Dehydronuciferine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-0090000000-35c7edbe7dcecd162344	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydronuciferine 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 - Dehydronuciferine 10V, Positive-QTOF	splash10-0006-0090000000-5ebb5916438c9c986560	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 20V, Positive-QTOF	splash10-0006-0090000000-b6f04fb9d782244350be	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 40V, Positive-QTOF	splash10-0f7t-1090000000-6543a5568d03cfb9345b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 10V, Negative-QTOF	splash10-0006-0090000000-bf367de881fc92b53230	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 20V, Negative-QTOF	splash10-0006-0090000000-f166a65b4c14d0161018	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 40V, Negative-QTOF	splash10-002b-0090000000-7c8a7419b5b1b8ad9ab9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 10V, Negative-QTOF	splash10-0006-0090000000-80f6742b4f6b5e8352cf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 20V, Negative-QTOF	splash10-0006-0090000000-393f18b89c0bd9306fa7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 40V, Negative-QTOF	splash10-0002-0090000000-37a1306bec044b036580	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 10V, Positive-QTOF	splash10-0006-0090000000-c0ae6c1ee6eacc17ae1d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 20V, Positive-QTOF	splash10-0006-0090000000-c0ae6c1ee6eacc17ae1d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronuciferine 40V, Positive-QTOF	splash10-0006-0190000000-cbc3b05b54cfc87b730c	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

FDB011863

KNApSAcK ID

C00054276

Chemspider ID

717588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318294

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 Dehydronuciferine (HMDB0033737)

MOL for HMDB0033737 (Dehydronuciferine)

3D MOL for HMDB0033737 (Dehydronuciferine)

3D SDF for HMDB0033737 (Dehydronuciferine)

3D-SDF for HMDB0033737 (Dehydronuciferine)

PDB for HMDB0033737 (Dehydronuciferine)

3D PDB for HMDB0033737 (Dehydronuciferine)

SMILES for HMDB0033737 (Dehydronuciferine)

INCHI for HMDB0033737 (Dehydronuciferine)

Structure for HMDB0033737 (Dehydronuciferine)

3D Structure for HMDB0033737 (Dehydronuciferine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra