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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:22 UTC

Update Date

2022-03-07 02:52:35 UTC

HMDB ID

HMDB0030516

Secondary Accession Numbers

HMDB30516

Metabolite Identification

Common Name

Petasinine

Description

Petasinine belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. Based on a literature review very few articles have been published on Petasinine.

Structure

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

HMDB0030516
     RDKit          3D
Petasinine
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.3593    0.4977    1.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4443    0.4489    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3797    0.2840   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483    0.2461   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    0.1394    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089    0.1701    1.5470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9489   -0.0316   -0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609   -0.1817   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0760   -1.4098   -0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4709   -1.0455   -0.6211 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766   -1.8271    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -1.1607    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991    0.2421    1.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    0.2988   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887    0.9257   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175    1.1457   -1.9686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842    1.4800   -2.4949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9853   -0.4395    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7496    1.3731    2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3748    0.6684    2.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165    0.5523    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9190    1.0554   -2.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022    0.3442   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955   -0.7185   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -0.1340    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7491   -1.9229   -1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0439   -2.1661    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840   -1.7675   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1315   -2.9013    0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8065   -1.7447    2.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4948   -1.1774    1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658    0.4953    1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    0.9447    1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4079    0.8630   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155    1.8538    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823    0.2727   -2.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9970    2.0058   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2016    2.3211   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  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
 15  8  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END


  Mrv0541 05061305182D          

 17 18  0  0  0  0            999 V2000
    4.1167   -0.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292    0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312    3.1160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    0.0635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  2  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 16 13  2  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030516

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(\C)C(=O)OC1CN2CCCC2C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO3/c1-3-9(2)13(16)17-12-7-14-6-4-5-11(14)10(12)8-15/h3,10-12,15H,4-8H2,1-2H3/b9-3-

> <INCHI_KEY>
HQARVRYBUBTANR-OQFOIZHKSA-N

> <FORMULA>
C13H21NO3

> <MOLECULAR_WEIGHT>
239.3107

> <EXACT_MASS>
239.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.61575929049358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(hydroxymethyl)-hexahydro-1H-pyrrolizin-2-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.430495184333332

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.337008487394474

> <JCHEM_PKA_STRONGEST_BASIC>
8.917207730822101

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
65.8723

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(hydroxymethyl)-hexahydro-1H-pyrrolizin-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030516
     RDKit          3D
Petasinine
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.3593    0.4977    1.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4443    0.4489    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3797    0.2840   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483    0.2461   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    0.1394    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089    0.1701    1.5470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9489   -0.0316   -0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609   -0.1817   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0760   -1.4098   -0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4709   -1.0455   -0.6211 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766   -1.8271    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -1.1607    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991    0.2421    1.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    0.2988   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887    0.9257   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175    1.1457   -1.9686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842    1.4800   -2.4949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9853   -0.4395    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7496    1.3731    2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3748    0.6684    2.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165    0.5523    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9190    1.0554   -2.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022    0.3442   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955   -0.7185   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -0.1340    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7491   -1.9229   -1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0439   -2.1661    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840   -1.7675   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1315   -2.9013    0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8065   -1.7447    2.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4948   -1.1774    1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658    0.4953    1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    0.9447    1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4079    0.8630   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155    1.8538    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823    0.2727   -2.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9970    2.0058   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2016    2.3211   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  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
 15  8  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  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       7.685  -1.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.455   2.786   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.455   0.119   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.905   2.786   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.032   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.929   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.405   5.496   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.685   1.452   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.929   4.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.465   3.556   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.835   2.786   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.145   1.452   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.465   2.016   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       4.912   5.817   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.375   0.119   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.375   2.786   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    9                                                            
CONECT    3    1    9                                                       
CONECT    4    5    6                                                       
CONECT    5    4   11                                                       
CONECT    6    4   14                                                       
CONECT    7   12   14                                                       
CONECT    8   10   15                                                       
CONECT    9    2    3   13                                                  
CONECT   10    8   11   12                                                  
CONECT   11    5   10   14                                                  
CONECT   12    7   10   17                                                  
CONECT   13    9   16   17                                                  
CONECT   14    6    7   11                                                  
CONECT   15    8                                                            
CONECT   16   13                                                            
CONECT   17   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0030516
HETATM    1  C1  UNL     1       4.359   0.498   1.981  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.444   0.449   0.499  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.380   0.284  -0.252  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.548   0.246  -1.725  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.053   0.139   0.326  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.909   0.170   1.547  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.949  -0.032  -0.451  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.361  -0.182  -0.061  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.076  -1.410  -0.423  1.00  0.00           C  
HETATM   10  N1  UNL     1      -2.471  -1.046  -0.621  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.377  -1.827   0.156  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.430  -1.161   1.516  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.899   0.242   1.323  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.628   0.299  -0.138  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.289   0.926  -0.477  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.317   1.146  -1.969  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.084   1.480  -2.495  1.00  0.00           O  
HETATM   18  H1  UNL     1       3.985  -0.440   2.426  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.750   1.373   2.335  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.375   0.668   2.404  1.00  0.00           H  
HETATM   21  H4  UNL     1       5.417   0.552   0.012  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.919   1.055  -2.162  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.602   0.344  -2.014  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.095  -0.719  -2.078  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.343  -0.134   1.071  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.749  -1.923  -1.340  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.044  -2.166   0.391  1.00  0.00           H  
HETATM   28  H11 UNL     1      -4.384  -1.767  -0.345  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.132  -2.901   0.214  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.807  -1.745   2.227  1.00  0.00           H  
HETATM   31  H14 UNL     1      -4.495  -1.177   1.830  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.066   0.495   1.975  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.734   0.945   1.567  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.408   0.863  -0.692  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.116   1.854   0.093  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.782   0.273  -2.451  1.00  0.00           H  
HETATM   37  H20 UNL     1      -1.997   2.006  -2.151  1.00  0.00           H  
HETATM   38  H21 UNL     1       0.202   2.321  -2.049  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   21
CONECT    3    4    5
CONECT    4   22   23   24
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   15   25
CONECT    9   10   26   27
CONECT   10   11   14
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   32   33
CONECT   14   15   34
CONECT   15   16   35
CONECT   16   17   36   37
CONECT   17   38
END

HMDB0030516
     RDKit          3D
Petasinine
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.3593    0.4977    1.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4443    0.4489    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3797    0.2840   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483    0.2461   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    0.1394    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089    0.1701    1.5470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9489   -0.0316   -0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609   -0.1817   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0760   -1.4098   -0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4709   -1.0455   -0.6211 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766   -1.8271    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -1.1607    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991    0.2421    1.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    0.2988   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887    0.9257   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175    1.1457   -1.9686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0842    1.4800   -2.4949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9853   -0.4395    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7496    1.3731    2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3748    0.6684    2.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165    0.5523    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9190    1.0554   -2.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022    0.3442   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955   -0.7185   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -0.1340    1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7491   -1.9229   -1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0439   -2.1661    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840   -1.7675   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1315   -2.9013    0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8065   -1.7447    2.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4948   -1.1774    1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658    0.4953    1.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    0.9447    1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4079    0.8630   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155    1.8538    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823    0.2727   -2.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9970    2.0058   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2016    2.3211   -2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  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
 15  8  1  0
 14 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(Hydroxymethyl)-hexahydro-1H-pyrrolizin-2-yl (2Z)-2-methylbut-2-enoic acid	HMDB

Chemical Formula

C₁₃H₂₁NO₃

Average Molecular Weight

239.3107

Monoisotopic Molecular Weight

239.152143543

IUPAC Name

1-(hydroxymethyl)-hexahydro-1H-pyrrolizin-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

1-(hydroxymethyl)-hexahydro-1H-pyrrolizin-2-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

70474-33-8

SMILES

C\C=C(\C)C(=O)OC1CN2CCCC2C1CO

InChI Identifier

InChI=1S/C13H21NO3/c1-3-9(2)13(16)17-12-7-14-6-4-5-11(14)10(12)8-15/h3,10-12,15H,4-8H2,1-2H3/b9-3-

InChI Key

HQARVRYBUBTANR-OQFOIZHKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
Fatty acid ester
N-alkylpyrrolidine
Fatty acyl
1,3-aminoalcohol
Pyrrolidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Primary alcohol
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030516)
Cytoplasm (HMDB: HMDB0030516)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030516)

Source

Endogenous

Endogenous (HMDB: HMDB0030516)

Plant

Plant (HMDB: HMDB0030516)

Exogenous

Food

Food (HMDB: HMDB0030516)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

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
Water Solubility	59.6 g/L	ALOGPS
logP	1.12	ALOGPS
logP	1.43	ChemAxon
logS	-0.6	ALOGPS
pKa (Strongest Acidic)	15.34	ChemAxon
pKa (Strongest Basic)	8.92	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	4	ChemAxon
Refractivity	65.87 m³·mol⁻¹	ChemAxon
Polarizability	26.62 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	155.697	31661259
DarkChem	[M-H]-	153.163	31661259
DeepCCS	[M+H]+	155.911	30932474
DeepCCS	[M-H]-	153.553	30932474
DeepCCS	[M-2H]-	187.208	30932474
DeepCCS	[M+Na]+	162.224	30932474
AllCCS	[M+H]+	156.1	32859911
AllCCS	[M+H-H2O]+	152.5	32859911
AllCCS	[M+NH4]+	159.5	32859911
AllCCS	[M+Na]+	160.5	32859911
AllCCS	[M-H]-	160.5	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Petasinine	C\C=C(\C)C(=O)OC1CN2CCCC2C1CO	2622.5	Standard polar	33892256
Petasinine	C\C=C(\C)C(=O)OC1CN2CCCC2C1CO	1822.9	Standard non polar	33892256
Petasinine	C\C=C(\C)C(=O)OC1CN2CCCC2C1CO	1948.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Petasinine,1TMS,isomer #1	C/C=C(/C)C(=O)OC1CN2CCCC2C1CO[Si](C)(C)C	1897.2	Semi standard non polar	33892256
Petasinine,1TBDMS,isomer #1	C/C=C(/C)C(=O)OC1CN2CCCC2C1CO[Si](C)(C)C(C)(C)C	2148.9	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 - Petasinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-06si-9510000000-9c9f1882ca8ae1b0836f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petasinine GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9520000000-16be9903dc77995895cc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petasinine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petasinine 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 - Petasinine 10V, Positive-QTOF	splash10-006x-2490000000-e15c6ea4c43daa66bd6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 20V, Positive-QTOF	splash10-00dl-9720000000-b5568f17cd8b73599ad5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 40V, Positive-QTOF	splash10-0kur-9200000000-70e76599339c561d09e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 10V, Negative-QTOF	splash10-000i-1190000000-eae71666f8a19a05976a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 20V, Negative-QTOF	splash10-0a4i-5890000000-8c49ce74e6ccff24e400	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 40V, Negative-QTOF	splash10-01oy-9500000000-b470c1593672167ca46a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 10V, Negative-QTOF	splash10-000i-4590000000-99107ea471494dadc464	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 20V, Negative-QTOF	splash10-0002-9010000000-a18af6e6e5f97f80269f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 40V, Negative-QTOF	splash10-0a4i-9210000000-7cc7d9fead6211ccba31	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 10V, Positive-QTOF	splash10-052f-0910000000-7d0c3b97c8c423fc378f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 20V, Positive-QTOF	splash10-00di-1900000000-8026c38ee99cf27e4e18	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasinine 40V, Positive-QTOF	splash10-05fr-9500000000-a14c6c7cb767eebe11d8	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

FDB002388

KNApSAcK ID

C00057509

Chemspider ID

35013218

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751042

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 Petasinine (HMDB0030516)

MOL for HMDB0030516 (Petasinine)

3D MOL for HMDB0030516 (Petasinine)

3D SDF for HMDB0030516 (Petasinine)

3D-SDF for HMDB0030516 (Petasinine)

PDB for HMDB0030516 (Petasinine)

3D PDB for HMDB0030516 (Petasinine)

SMILES for HMDB0030516 (Petasinine)

INCHI for HMDB0030516 (Petasinine)

Structure for HMDB0030516 (Petasinine)

3D Structure for HMDB0030516 (Petasinine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra