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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:12:50 UTC

Update Date

2022-03-07 02:53:43 UTC

HMDB ID

HMDB0033481

Secondary Accession Numbers

HMDB33481

Metabolite Identification

Common Name

Baptifoline

Description

Baptifoline, also known as alkaloid P3?, belongs to the class of organic compounds known as anagyrine-type alkaloids. These are lupin alkaloids with a structure based on the anagyrine skeleton. Anagyrine is a tetracyclic ketone containing a quinolizidine, and two pyridine rings fused together to form dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one. Baptifoline is a very strong basic compound (based on its pKa). Outside of the human body, baptifoline has been detected, but not quantified in, coffee and coffee products. This could make baptifoline a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033481
     RDKit          3D
Baptifoline
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.3900    1.5256    2.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305    0.8382    1.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    0.3827    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -0.3689   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5332   -0.6409   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -0.1617   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    0.5594    0.6203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    1.0832    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0270    1.1996    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    0.9543   -1.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0605   -0.4248   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617   -1.4020   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -0.8572   -0.4475 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -1.7623   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4903   -1.0345   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.3870   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964    0.6275    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942    0.8874    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670    0.2220    0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378    0.6195    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685   -0.7362   -0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -1.2160   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622    2.0235    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688    0.3364    1.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621    2.2274    0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360    0.8631   -1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    1.7070   -1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1974   -0.7432   -2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354   -2.3924   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5315   -1.5983    0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -2.1126    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -2.6171   -0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519   -1.1337   -1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3954   -1.6084   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5753    1.0360   -1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830    0.6938    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775    0.8780    1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    1.9818    0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9200   -0.2236    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 19  9  1  0
 11  6  1  0
 19 13  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv0541 05061307082D          

 19 22  0  0  0  0            999 V2000
   -0.3627    2.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3752    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636    2.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015    2.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    1.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625    0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4246    1.2107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605    0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408    0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605    0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625   -0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0824   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -1.2427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -2.0676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340   -2.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0550   -2.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683   -1.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628   -2.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033481

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h1-3,10-12,14,18H,4-9H2

> <INCHI_KEY>
AOOCSKCGZYCEJX-UHFFFAOYSA-N

> <FORMULA>
C15H20N2O2

> <MOLECULAR_WEIGHT>
260.3315

> <EXACT_MASS>
260.152477894

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.89396993673145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
-0.5189790070000008

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.169454069354025

> <JCHEM_PKA_STRONGEST_BASIC>
8.670226444811446

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
75.61749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033481
     RDKit          3D
Baptifoline
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.3900    1.5256    2.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305    0.8382    1.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    0.3827    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -0.3689   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5332   -0.6409   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -0.1617   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    0.5594    0.6203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    1.0832    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0270    1.1996    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    0.9543   -1.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0605   -0.4248   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617   -1.4020   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -0.8572   -0.4475 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -1.7623   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4903   -1.0345   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.3870   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964    0.6275    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942    0.8874    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670    0.2220    0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378    0.6195    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685   -0.7362   -0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -1.2160   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622    2.0235    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688    0.3364    1.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621    2.2274    0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360    0.8631   -1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    1.7070   -1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1974   -0.7432   -2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354   -2.3924   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5315   -1.5983    0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -2.1126    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -2.6171   -0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519   -1.1337   -1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3954   -1.6084   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5753    1.0360   -1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830    0.6938    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775    0.8780    1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    1.9818    0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9200   -0.2236    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 19  9  1  0
 11  6  1  0
 19 13  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  O   UNK     0      -0.677   4.486   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.700   3.797   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.985   4.646   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.363   3.957   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.455   2.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170   1.571   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.793   2.260   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.673   1.571   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.823   0.074   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.673   0.074   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.170  -0.074   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.020  -1.571   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.673  -2.320   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.698  -3.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.623  -4.651   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.969  -3.902   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.994  -2.362   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.673  -1.571   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.291  -4.694   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18    9   13   17                                                  
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0033481
HETATM    1  O1  UNL     1      -3.390   1.526   2.383  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.430   0.838   1.324  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.636   0.383   0.904  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.702  -0.369  -0.248  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.533  -0.641  -0.951  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.324  -0.162  -0.496  1.00  0.00           C  
HETATM    7  N1  UNL     1      -2.299   0.559   0.620  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.087   1.083   1.168  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.027   1.200   0.190  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.367   0.954  -1.246  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.060  -0.425  -1.230  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.162  -1.402  -0.501  1.00  0.00           C  
HETATM   13  N2  UNL     1       1.146  -0.857  -0.448  1.00  0.00           N  
HETATM   14  C11 UNL     1       2.225  -1.762  -0.268  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.490  -1.035  -0.674  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.545   0.387  -0.281  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.796   0.628   0.335  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.494   0.887   0.627  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.167   0.222   0.514  1.00  0.00           C  
HETATM   20  H1  UNL     1      -5.538   0.620   1.488  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.669  -0.736  -0.588  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.541  -1.216  -1.843  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.262   2.024   1.747  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.769   0.336   1.964  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.462   2.227   0.321  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.536   0.863  -1.848  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.032   1.707  -1.663  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.197  -0.743  -2.261  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.135  -2.392  -1.007  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.531  -1.598   0.528  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.346  -2.113   0.783  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.093  -2.617  -0.964  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.552  -1.134  -1.798  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.395  -1.608  -0.316  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.575   1.036  -1.206  1.00  0.00           H  
HETATM   36  H17 UNL     1       4.683   0.694   1.329  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.878   0.878   1.691  1.00  0.00           H  
HETATM   38  H19 UNL     1       2.336   1.982   0.418  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.920  -0.224   1.500  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4    4   20
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   11
CONECT    7    8
CONECT    8    9   23   24
CONECT    9   10   19   25
CONECT   10   11   26   27
CONECT   11   12   28
CONECT   12   13   29   30
CONECT   13   14   19
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   18   35
CONECT   17   36
CONECT   18   19   37   38
CONECT   19   39
END

HMDB0033481
     RDKit          3D
Baptifoline
 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.3900    1.5256    2.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4305    0.8382    1.3242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    0.3827    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -0.3689   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5332   -0.6409   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -0.1617   -0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    0.5594    0.6203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    1.0832    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0270    1.1996    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    0.9543   -1.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0605   -0.4248   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617   -1.4020   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -0.8572   -0.4475 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -1.7623   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4903   -1.0345   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.3870   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964    0.6275    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942    0.8874    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670    0.2220    0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378    0.6195    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685   -0.7362   -0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -1.2160   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622    2.0235    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688    0.3364    1.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621    2.2274    0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360    0.8631   -1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    1.7070   -1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1974   -0.7432   -2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354   -2.3924   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5315   -1.5983    0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -2.1126    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928   -2.6171   -0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519   -1.1337   -1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3954   -1.6084   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5753    1.0360   -1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830    0.6938    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775    0.8780    1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    1.9818    0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9200   -0.2236    1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 19  9  1  0
 11  6  1  0
 19 13  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Baptifoline	HMDB
13-Hydroxyanagyrine	HMDB
Alkaloid P3?	HMDB
Baptifoline	MeSH

Chemical Formula

C₁₅H₂₀N₂O₂

Average Molecular Weight

260.3315

Monoisotopic Molecular Weight

260.152477894

IUPAC Name

12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

Traditional Name

12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

CAS Registry Number

732-50-3

SMILES

OC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C1

InChI Identifier

InChI=1S/C15H20N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h1-3,10-12,14,18H,4-9H2

InChI Key

AOOCSKCGZYCEJX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anagyrine-type alkaloids. These are lupin alkaloids with a structure based on the anagyrine skeleton. Anagyrine is a tetracyclic ketone containing a quinolizidine, and two pyridine rings fused together to form dipyrido[1,2-a:1',2'-E][1,5]diazocin-4-one.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Anagyrine-type alkaloids

Direct Parent

Anagyrine-type alkaloids

Alternative Parents

Substituents

Anagyrine-type alkaloid
Quinolizidine
Pyridinone
Aralkylamine
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033481)
Cytoplasm (HMDB: HMDB0033481)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033481)

Source

Exogenous

Food

Food (HMDB: HMDB0033481)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0033481)

Not Available

Nutrient (HMDB: HMDB0033481)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 °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	22.4 g/L	ALOGPS
logP	1.2	ALOGPS
logP	-0.52	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	15.17	ChemAxon
pKa (Strongest Basic)	8.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.62 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.913	31661259
DarkChem	[M-H]-	159.259	31661259
DeepCCS	[M-2H]-	194.185	30932474
DeepCCS	[M+Na]+	169.733	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	171.9	32859911
AllCCS	[M+Na-2H]-	171.7	32859911
AllCCS	[M+HCOO]-	171.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Baptifoline	OC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C1	3245.3	Standard polar	33892256
Baptifoline	OC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C1	2631.2	Standard non polar	33892256
Baptifoline	OC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C1	2624.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Baptifoline,1TMS,isomer #1	C[Si](C)(C)OC1CCN2CC3CC(CN4C3=CC=CC4=O)C2C1	2456.4	Semi standard non polar	33892256
Baptifoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCN2CC3CC(CN4C3=CC=CC4=O)C2C1	2712.4	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 - Baptifoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-2590000000-07f6ebf71fc39939f9f6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baptifoline GC-MS (1 TMS) - 70eV, Positive	splash10-0300-6981000000-df090227ddc3c6127b1d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baptifoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baptifoline 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 - Baptifoline 10V, Positive-QTOF	splash10-01ox-0090000000-843960a8489ba4f1d0ec	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 20V, Positive-QTOF	splash10-01ox-0190000000-f0a5c4b7858f49c5f20f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 40V, Positive-QTOF	splash10-029i-3980000000-54bed17f205c1e0a2f93	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 10V, Negative-QTOF	splash10-0a4i-0090000000-bbddfb9941122293598c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 20V, Negative-QTOF	splash10-0a4l-0090000000-e65b7d3569bc1b821def	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 40V, Negative-QTOF	splash10-052r-1910000000-476f26b4ec1e0d9cf647	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 10V, Positive-QTOF	splash10-03dl-0090000000-23a2d02f90f9c77c62eb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 20V, Positive-QTOF	splash10-03di-0090000000-cceec67e03d09ea4c1c9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 40V, Positive-QTOF	splash10-03dj-1920000000-0103307c92ac3f5847c2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 10V, Negative-QTOF	splash10-0a4i-0090000000-a7fd50b20d0fcccddc5f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 20V, Negative-QTOF	splash10-0a4i-0090000000-07f5a21deeb00c44100c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baptifoline 40V, Negative-QTOF	splash10-0udi-2890000000-0fdc09be8ab72096b5e8	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

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

621307

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 Baptifoline (HMDB0033481)

MOL for HMDB0033481 (Baptifoline)

3D MOL for HMDB0033481 (Baptifoline)

3D SDF for HMDB0033481 (Baptifoline)

3D-SDF for HMDB0033481 (Baptifoline)

PDB for HMDB0033481 (Baptifoline)

3D PDB for HMDB0033481 (Baptifoline)

SMILES for HMDB0033481 (Baptifoline)

INCHI for HMDB0033481 (Baptifoline)

Structure for HMDB0033481 (Baptifoline)

3D Structure for HMDB0033481 (Baptifoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra