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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:58:54 UTC

Update Date

2021-09-23 06:58:54 UTC

HMDB ID

HMDB0302142

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Thesinine

Description

Thesinine is a member of the class of compounds known as coumaric acid esters. Coumaric acid esters are aromatic compounds containing an ester derivative of coumaric acid. Thesinine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Thesinine can be found in borage, which makes thesinine a potential biomarker for the consumption of this food product. Thesinine is a pyrrolizidine alkaloid first isolated from Thesium minkwitzianum from which it derives its name. It is also found in the flowers and seeds of borage .

Structure

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

HMDB0302142
     RDKit          3D
Thesinine
 42 44  0  0  0  0  0  0  0  0999 V2000
    0.0156   -2.3150   -0.7074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218   -1.1844   -0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923   -1.0774   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    0.0725   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378    0.2357   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9284   -0.8106   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3111   -0.6233   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8334    0.6393   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2021    0.8671    0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9453    1.6923   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841    1.5179   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2837   -0.0847   -0.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6759   -0.1909   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -0.9531    0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907   -0.1759    1.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536    0.8866    1.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551    0.1879    1.4894 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    1.0015    0.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6695    0.0153   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4135   -0.7382   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6964   -0.9143    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816   -1.9663   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416    0.9601   -0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5756   -1.8181   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0003   -1.4538   -0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7243    1.0117   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3247    2.7033    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    2.3342   -0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795   -0.6565   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914    0.8487   -0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310   -1.9724    0.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754   -0.8081    2.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    0.2868    1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    1.3265    2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786    1.6655    1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7364    1.5019    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4615    1.7285    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3302   -0.6563    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1741    0.5221   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960   -1.6893   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9057   -0.0424   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0408   -1.8745    1.0948 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 11  5  1  0
 21 14  1  0
 21 17  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
M  END

  Mrv0541 02241216422D          

 21 23  0  0  0  0            999 V2000
    1.0265   -1.1735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198   -1.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0344   -2.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8191   -2.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6036   -2.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0873   -2.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6036   -3.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8191   -3.2086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0344   -3.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4507   -2.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807   -0.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0873   -0.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7283    0.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9825    1.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4302    1.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6884    2.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1388    3.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6692    2.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275    2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780    1.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2188    3.4642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302142

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(\C=C\C(=O)OCC2CCN3CCCC23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c19-15-6-3-13(4-7-15)5-8-17(20)21-12-14-9-11-18-10-1-2-16(14)18/h3-8,14,16,19H,1-2,9-12H2/b8-5+

> <INCHI_KEY>
FQVNMXZPGWLUFZ-VMPITWQZSA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.3535

> <EXACT_MASS>
287.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.14940751143542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
1.7364013282750148

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.339377350055676

> <JCHEM_PKA_STRONGEST_BASIC>
10.292831616786357

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
82.59040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302142
     RDKit          3D
Thesinine
 42 44  0  0  0  0  0  0  0  0999 V2000
    0.0156   -2.3150   -0.7074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218   -1.1844   -0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923   -1.0774   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    0.0725   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378    0.2357   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9284   -0.8106   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3111   -0.6233   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8334    0.6393   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2021    0.8671    0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9453    1.6923   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841    1.5179   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2837   -0.0847   -0.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6759   -0.1909   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -0.9531    0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907   -0.1759    1.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536    0.8866    1.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551    0.1879    1.4894 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    1.0015    0.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6695    0.0153   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4135   -0.7382   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6964   -0.9143    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816   -1.9663   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416    0.9601   -0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5756   -1.8181   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0003   -1.4538   -0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7243    1.0117   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3247    2.7033    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    2.3342   -0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795   -0.6565   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914    0.8487   -0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310   -1.9724    0.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754   -0.8081    2.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    0.2868    1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    1.3265    2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786    1.6655    1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7364    1.5019    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4615    1.7285    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3302   -0.6563    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1741    0.5221   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960   -1.6893   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9057   -0.0424   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0408   -1.8745    1.0948 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 11  5  1  0
 21 14  1  0
 21 17  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.916  -2.191   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.410  -2.511   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.064  -3.976   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.529  -4.453   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.993  -3.976   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.896  -5.220   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.993  -6.467   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.529  -5.989   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.064  -6.467   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.841  -5.220   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.391  -0.726   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.896  -0.405   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.359   0.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.834   1.883   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.803   3.027   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.285   4.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.259   5.635   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.249   5.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.731   3.855   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.706   2.706   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.275   6.467   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    3    9                                                       
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   15   19                                                       
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0302142
HETATM    1  O1  UNL     1       0.016  -2.315  -0.707  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.522  -1.184  -0.589  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.992  -1.077  -0.484  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.594   0.073  -0.358  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.038   0.236  -0.251  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.928  -0.811  -0.272  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.311  -0.623  -0.167  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.833   0.639  -0.038  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.202   0.867   0.069  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.945   1.692  -0.016  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.584   1.518  -0.118  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.284  -0.085  -0.558  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.676  -0.191  -0.651  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.198  -0.953   0.514  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.791  -0.176   1.774  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.854   0.887   1.830  1.00  0.00           C  
HETATM   17  N1  UNL     1      -4.055   0.188   1.489  1.00  0.00           N  
HETATM   18  C14 UNL     1      -5.005   1.002   0.781  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.669   0.015  -0.190  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.413  -0.738  -0.657  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.696  -0.914   0.642  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.582  -1.966  -0.513  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.942   0.960  -0.334  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.576  -1.818  -0.371  1.00  0.00           H  
HETATM   25  H4  UNL     1       7.000  -1.454  -0.185  1.00  0.00           H  
HETATM   26  H5  UNL     1       8.724   1.012  -0.785  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.325   2.703   0.085  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.886   2.334  -0.102  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.980  -0.656  -1.619  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.091   0.849  -0.694  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.831  -1.972   0.536  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.775  -0.808   2.661  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.787   0.287   1.575  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.871   1.326   2.849  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.679   1.666   1.075  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.736   1.502   1.423  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.462   1.728   0.108  1.00  0.00           H  
HETATM   38  H17 UNL     1      -6.330  -0.656   0.405  1.00  0.00           H  
HETATM   39  H18 UNL     1      -6.174   0.522  -1.013  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.696  -1.689  -1.145  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.906  -0.042  -1.354  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.041  -1.874   1.095  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6    6   11
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13
CONECT   13   14   29   30
CONECT   14   15   21   31
CONECT   15   16   32   33
CONECT   16   17   34   35
CONECT   17   18   21
CONECT   18   19   36   37
CONECT   19   20   38   39
CONECT   20   21   40   41
CONECT   21   42
END

HMDB0302142
     RDKit          3D
Thesinine
 42 44  0  0  0  0  0  0  0  0999 V2000
    0.0156   -2.3150   -0.7074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218   -1.1844   -0.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923   -1.0774   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    0.0725   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378    0.2357   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9284   -0.8106   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3111   -0.6233   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8334    0.6393   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2021    0.8671    0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9453    1.6923   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841    1.5179   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2837   -0.0847   -0.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6759   -0.1909   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -0.9531    0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907   -0.1759    1.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536    0.8866    1.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551    0.1879    1.4894 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    1.0015    0.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6695    0.0153   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4135   -0.7382   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6964   -0.9143    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816   -1.9663   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416    0.9601   -0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5756   -1.8181   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0003   -1.4538   -0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7243    1.0117   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3247    2.7033    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    2.3342   -0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9795   -0.6565   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914    0.8487   -0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310   -1.9724    0.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754   -0.8081    2.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    0.2868    1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713    1.3265    2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786    1.6655    1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7364    1.5019    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4615    1.7285    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3302   -0.6563    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1741    0.5221   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960   -1.6893   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9057   -0.0424   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0408   -1.8745    1.0948 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 11  5  1  0
 21 14  1  0
 21 17  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Hexahydro-1H-pyrrolizin-1-yl)methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₇H₂₁NO₃

Average Molecular Weight

287.3535

Monoisotopic Molecular Weight

287.152143543

IUPAC Name

hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C\C(=O)OCC2CCN3CCCC23)C=C1

InChI Identifier

InChI=1S/C17H21NO3/c19-15-6-3-13(4-7-15)5-8-17(20)21-12-14-9-11-18-10-1-2-16(14)18/h3-8,14,16,19H,1-2,9-12H2/b8-5+

InChI Key

FQVNMXZPGWLUFZ-VMPITWQZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Pyrrolizidine
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
N-alkylpyrrolidine
Alpha,beta-unsaturated carboxylic ester
Pyrrolidine
Enoate ester
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302142)

Food

Herb and spice

Oilseed crop

Borage (FooDB: FOOD00026)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	2.3	ALOGPS
logP	1.74	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.59 m³·mol⁻¹	ChemAxon
Polarizability	32.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
AllCCS	[M+H]+	169.389	32859911
AllCCS	[M+H-H2O]+	166.008	32859911
AllCCS	[M+Na]+	173.424	32859911
AllCCS	[M+NH4]+	172.523	32859911
AllCCS	[M-H]-	172.328	32859911
AllCCS	[M+Na-2H]-	172.278	32859911
AllCCS	[M+HCOO]-	172.353	32859911
DeepCCS	[M-2H]-	201.414	30932474
DeepCCS	[M+Na]+	176.979	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 10V, Positive-QTOF	splash10-00dr-0940000000-254dca32e857942b46f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 20V, Positive-QTOF	splash10-00di-0900000000-eede8e8499508f414ea9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 40V, Positive-QTOF	splash10-05fr-9600000000-443a4593099d78042b63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 10V, Negative-QTOF	splash10-000j-0960000000-29b0edc846eb9121b650	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 20V, Negative-QTOF	splash10-01ot-0910000000-3f24287fde35461081e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 40V, Negative-QTOF	splash10-01ow-3900000000-e6cd141a24057c71a163	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 10V, Positive-QTOF	splash10-000i-0190000000-0bfdc44514ba65ac2fed	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 20V, Positive-QTOF	splash10-000i-0490000000-0df5748bed91e3211e83	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 40V, Positive-QTOF	splash10-00di-4900000000-37c9ac93823c7e473802	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 10V, Negative-QTOF	splash10-000i-0090000000-32affc6af32f5da1d257	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 20V, Negative-QTOF	splash10-000i-0980000000-5459e338276539a05669	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thesinine 40V, Negative-QTOF	splash10-014i-0900000000-b2fc4172c009211bd09d	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB002151

KNApSAcK ID

Not Available

Chemspider ID

59696295

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for Thesinine (HMDB0302142)

MOL for HMDB0302142 (Thesinine)

3D MOL for HMDB0302142 (Thesinine)

3D SDF for HMDB0302142 (Thesinine)

3D-SDF for HMDB0302142 (Thesinine)

PDB for HMDB0302142 (Thesinine)

3D PDB for HMDB0302142 (Thesinine)

SMILES for HMDB0302142 (Thesinine)

INCHI for HMDB0302142 (Thesinine)

Structure for HMDB0302142 (Thesinine)

3D Structure for HMDB0302142 (Thesinine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra