Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:15 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030344

Secondary Accession Numbers

HMDB30344

Metabolite Identification

Common Name

(R)-Pronuciferine

Description

(R)-Pronuciferine belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol (R)-Pronuciferine has been detected, but not quantified in, several different foods, such as sacred lotus (Nelumbo nucifera), robusta coffees (Coffea canephora), coffee and coffee products, arabica coffees (Coffea arabica), and poppies (Papaver). This could make (R)-pronuciferine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (R)-Pronuciferine.

Structure

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

HMDB0030344
     RDKit          3D
(R)-Pronuciferine
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.2004   -3.7761   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -2.3933   -0.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -1.7960   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6464   -2.5828   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6023   -1.9759    0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221   -0.6072    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578    0.2237   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -0.4147   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089    0.3674   -0.3571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854    0.7249    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    1.6280   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836    2.1694    1.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466    3.3307    1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    4.1525    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6606    5.2578    0.9642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412    3.6447   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035    2.4837   -1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735    1.4315   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8502    0.1960    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9290   -0.6018   -0.3731 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1552    0.1637   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9842   -1.7927    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744   -2.7317    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2573   -3.9896   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5600   -4.2909    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -4.1189   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -3.6488   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    0.2573    1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985    1.8351    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5566    0.4134    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876    1.6176    2.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    3.6682    2.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7620    4.2364   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    2.1405   -2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626    1.2565   -1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    2.3112   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    0.4765    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6176    0.1606    0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991   -0.1948   -1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.2152   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785   -2.2642    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785   -1.4616    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -3.5764    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -3.1454   -0.9305 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  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8  3  1  0
 17 11  1  0
 23  5  1  0
 19  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END


  Mrv0541 05061305102D          

 23 26  0  0  0  0            999 V2000
   -1.5558    0.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7295   -2.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7295    1.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2489    1.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8212    1.0966    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
    1.3018   -1.3929    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
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    2.5252    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
    2.0143   -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
    1.3018    0.2571    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
    0.9964    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795    3.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -1.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  6  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14 11  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 16  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19  7  1  0  0  0  0
 19  8  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 20  1  1  0  0  0  0
 20  9  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  2  0  0  0  0
 22  2  1  0  0  0  0
 22 15  1  0  0  0  0
 23  3  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030344

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C3C(CC22C=CC(=O)C=C2)N(C)CCC3=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO3/c1-20-9-6-12-10-15(22-2)18(23-3)17-16(12)14(20)11-19(17)7-4-13(21)5-8-19/h4-5,7-8,10,14H,6,9,11H2,1-3H3

> <INCHI_KEY>
WUYQEGNOQLRQAQ-UHFFFAOYSA-N

> <FORMULA>
C19H21NO3

> <MOLECULAR_WEIGHT>
311.3749

> <EXACT_MASS>
311.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.46167855674318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.4568883619999995

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.77572119183691

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
92.27

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030344
     RDKit          3D
(R)-Pronuciferine
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.2004   -3.7761   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -2.3933   -0.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -1.7960   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6464   -2.5828   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6023   -1.9759    0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221   -0.6072    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578    0.2237   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -0.4147   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089    0.3674   -0.3571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854    0.7249    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    1.6280   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836    2.1694    1.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466    3.3307    1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    4.1525    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6606    5.2578    0.9642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412    3.6447   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035    2.4837   -1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735    1.4315   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8502    0.1960    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9290   -0.6018   -0.3731 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1552    0.1637   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9842   -1.7927    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744   -2.7317    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2573   -3.9896   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5600   -4.2909    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -4.1189   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -3.6488   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    0.2573    1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985    1.8351    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5566    0.4134    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876    1.6176    2.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    3.6682    2.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7620    4.2364   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    2.1405   -2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626    1.2565   -1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    2.3112   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    0.4765    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6176    0.1606    0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991   -0.1948   -1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.2152   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785   -2.2642    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785   -1.4616    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -3.5764    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -3.1454   -0.9305 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  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8  3  1  0
 17 11  1  0
 23  5  1  0
 19  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  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      -2.904   0.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.095  -4.139   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.095   2.019   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.917   4.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.198   3.364   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.119   3.430   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.400   2.047   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.457   4.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.860   2.080   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -1.570  -0.290   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       4.255   6.031   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.094  -2.599   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.094   0.479   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    7   13                                                       
CONECT    5    8   13                                                       
CONECT    6    9   12                                                       
CONECT    7    4   19                                                       
CONECT    8    5   19                                                       
CONECT    9    6   20                                                       
CONECT   10   12   15                                                       
CONECT   11   14   19                                                       
CONECT   12    6   10   16                                                  
CONECT   13    4    5   21                                                  
CONECT   14   11   16   20                                                  
CONECT   15   10   18   22                                                  
CONECT   16   12   14   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   15   17   23                                                  
CONECT   19    7    8   11   17                                             
CONECT   20    1    9   14                                                  
CONECT   21   13                                                            
CONECT   22    2   15                                                       
CONECT   23    3   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0030344
HETATM    1  C1  UNL     1      -3.200  -3.776  -0.436  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.991  -2.393  -0.401  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.754  -1.796  -0.258  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.646  -2.583  -0.142  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.602  -1.976   0.002  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.622  -0.607   0.018  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.458   0.224  -0.096  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.667  -0.415  -0.237  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.809   0.367  -0.357  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.485   0.725   0.833  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.010   1.628  -0.068  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.084   2.169   1.294  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.447   3.331   1.640  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.149   4.153   0.659  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.661   5.258   0.964  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.241   3.645  -0.704  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.704   2.484  -1.021  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.474   1.432  -0.580  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.850   0.196   0.183  1.00  0.00           C  
HETATM   20  N1  UNL     1       2.929  -0.602  -0.373  1.00  0.00           N  
HETATM   21  C17 UNL     1       4.155   0.164  -0.308  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.984  -1.793   0.468  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.874  -2.732   0.095  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.257  -3.990  -0.131  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.560  -4.291   0.308  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.014  -4.119  -1.478  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.678  -3.649  -0.156  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.049   0.257   1.726  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.498   1.835   0.880  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.557   0.413   0.696  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.588   1.618   2.075  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.349   3.668   2.683  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.762   4.236  -1.465  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.791   2.141  -2.038  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.363   1.256  -1.656  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.072   2.311  -0.321  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.050   0.476   1.237  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.618   0.161   0.690  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.899  -0.195  -1.036  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.915   1.215  -0.600  1.00  0.00           H  
HETATM   41  H18 UNL     1       3.978  -2.264   0.448  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.778  -1.462   1.528  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.774  -3.576   0.815  1.00  0.00           H  
HETATM   44  H21 UNL     1       2.107  -3.145  -0.930  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   23
CONECT    6    7   19
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   28   29   30
CONECT   11   12   17   18
CONECT   12   13   13   31
CONECT   13   14   32
CONECT   14   15   15   16
CONECT   16   17   17   33
CONECT   17   34
CONECT   18   19   35   36
CONECT   19   20   37
CONECT   20   21   22
CONECT   21   38   39   40
CONECT   22   23   41   42
CONECT   23   43   44
END

HMDB0030344
     RDKit          3D
(R)-Pronuciferine
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.2004   -3.7761   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -2.3933   -0.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -1.7960   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6464   -2.5828   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6023   -1.9759    0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221   -0.6072    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578    0.2237   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -0.4147   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089    0.3674   -0.3571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854    0.7249    0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    1.6280   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836    2.1694    1.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466    3.3307    1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    4.1525    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6606    5.2578    0.9642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2412    3.6447   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035    2.4837   -1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735    1.4315   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8502    0.1960    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9290   -0.6018   -0.3731 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1552    0.1637   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9842   -1.7927    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744   -2.7317    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2573   -3.9896   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5600   -4.2909    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135   -4.1189   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -3.6488   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    0.2573    1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985    1.8351    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5566    0.4134    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876    1.6176    2.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489    3.6682    2.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7620    4.2364   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    2.1405   -2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626    1.2565   -1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    2.3112   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0501    0.4765    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6176    0.1606    0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991   -0.1948   -1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.2152   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785   -2.2642    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785   -1.4616    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -3.5764    0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -3.1454   -0.9305 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  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  8  3  1  0
 17 11  1  0
 23  5  1  0
 19  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Pronuciferine	HMDB
Milthanthine	HMDB
N,O-Dimethylcrotonosine	HMDB
N-Methylstepharine	HMDB
Pronuciferin	HMDB
Pronuciferine	HMDB

Chemical Formula

C₁₉H₂₁NO₃

Average Molecular Weight

311.3749

Monoisotopic Molecular Weight

311.152143543

IUPAC Name

10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one

Traditional Name

10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one

CAS Registry Number

2128-60-1

SMILES

COC1=C(OC)C2=C3C(CC22C=CC(=O)C=C2)N(C)CCC3=C1

InChI Identifier

InChI=1S/C19H21NO3/c1-20-9-6-12-10-15(22-2)18(23-3)17-16(12)14(20)11-19(17)7-4-13(21)5-8-19/h4-5,7-8,10,14H,6,9,11H2,1-3H3

InChI Key

WUYQEGNOQLRQAQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Proaporphines

Sub Class

Not Available

Direct Parent

Proaporphines

Alternative Parents

Substituents

Proaporphine
Tetrahydroisoquinoline
Indane
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Ketone
Tertiary amine
Cyclic ketone
Tertiary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030344)
Cell membrane (HMDB: HMDB0030344)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030344)

Source

Endogenous

Endogenous (HMDB: HMDB0030344)

Plant

Plant (HMDB: HMDB0030344)
Coffea (HMDB: HMDB0030344)

Exogenous

Food

Food (HMDB: HMDB0030344)

Fruit

Tropical fruit

Cherimoya (FooDB: FOOD00326)

Herb and spice

Oilseed crop

Poppy (FooDB: FOOD00127)

Vegetable

Other vegetable

Sacred lotus (FooDB: FOOD00402)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0030344)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	127 - 129 °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	0.11 g/L	ALOGPS
logP	2.51	ALOGPS
logP	2.46	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	7.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.27 m³·mol⁻¹	ChemAxon
Polarizability	33.46 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]+	174.659	31661259
DarkChem	[M-H]-	170.247	31661259
DeepCCS	[M-2H]-	209.476	30932474
DeepCCS	[M+Na]+	184.703	30932474
AllCCS	[M+H]+	174.5	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.6	32859911
AllCCS	[M+Na]+	178.5	32859911
AllCCS	[M-H]-	181.9	32859911
AllCCS	[M+Na-2H]-	181.6	32859911
AllCCS	[M+HCOO]-	181.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.82 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3279 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.92 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1380.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	199.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	313.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	328.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	468.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	884.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	298.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	928.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	238.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	239.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	442.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	442.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Pronuciferine	COC1=C(OC)C2=C3C(CC22C=CC(=O)C=C2)N(C)CCC3=C1	3772.5	Standard polar	33892256
(R)-Pronuciferine	COC1=C(OC)C2=C3C(CC22C=CC(=O)C=C2)N(C)CCC3=C1	2565.3	Standard non polar	33892256
(R)-Pronuciferine	COC1=C(OC)C2=C3C(CC22C=CC(=O)C=C2)N(C)CCC3=C1	2695.1	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 - (R)-Pronuciferine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0090000000-86334b4a99135535b468	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Pronuciferine 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 - (R)-Pronuciferine 10V, Positive-QTOF	splash10-03di-0059000000-24ed1e33f6d78af24232	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 20V, Positive-QTOF	splash10-01q9-0092000000-f4f2970614db51a81d97	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 40V, Positive-QTOF	splash10-0v00-2090000000-14cc8227698e8328a57e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 10V, Negative-QTOF	splash10-03di-0009000000-35a9eef82c86df85fa6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 20V, Negative-QTOF	splash10-03di-0079000000-79ce4bd105b65de6f1df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 40V, Negative-QTOF	splash10-03kc-0090000000-86e72526e0832cd9e0b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 10V, Positive-QTOF	splash10-03di-0009000000-9f3b29c8dcdf015b99e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 20V, Positive-QTOF	splash10-03di-0039000000-5009deaf9268e5c4f8a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 40V, Positive-QTOF	splash10-0909-1090000000-41fa0a4fc39efba03adc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 10V, Negative-QTOF	splash10-03di-0009000000-9bf675b2e28db05b0d3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 20V, Negative-QTOF	splash10-03di-0009000000-7c0bcc885755bb30ace8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pronuciferine 40V, Negative-QTOF	splash10-0a4i-1049000000-bd5ec9bb499964d23c7e	2021-09-22	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

628376

PDB ID

Not Available

ChEBI ID

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 (R)-Pronuciferine (HMDB0030344)

MOL for HMDB0030344 ((R)-Pronuciferine)

3D MOL for HMDB0030344 ((R)-Pronuciferine)

3D SDF for HMDB0030344 ((R)-Pronuciferine)

3D-SDF for HMDB0030344 ((R)-Pronuciferine)

PDB for HMDB0030344 ((R)-Pronuciferine)

3D PDB for HMDB0030344 ((R)-Pronuciferine)

SMILES for HMDB0030344 ((R)-Pronuciferine)

INCHI for HMDB0030344 ((R)-Pronuciferine)

Structure for HMDB0030344 ((R)-Pronuciferine)

3D Structure for HMDB0030344 ((R)-Pronuciferine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra