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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:16:30 UTC

Update Date

2022-03-07 02:56:42 UTC

HMDB ID

HMDB0040699

Secondary Accession Numbers

HMDB40699

Metabolite Identification

Common Name

Feruperine

Description

Feruperine belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Feruperine has been detected, but not quantified in, herbs and spices and pepper (spice). This could make feruperine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Feruperine.

Structure

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

HMDB0040699
     RDKit          3D
Feruperine
 42 43  0  0  0  0  0  0  0  0999 V2000
    6.4815   -0.3734   -2.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739   -0.7497   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1990   -0.4203   -0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833    0.2463   -1.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717    0.6073   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674    1.3948   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819    1.4125   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422    0.6625   -0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2878    0.8193   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914    0.0766    0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139   -0.7190    1.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    0.2314    0.9996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2640    1.1212    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0364    0.2953   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3194   -1.0565   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6224   -0.7881    1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -0.5306    1.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8859    0.2407    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182   -0.4440    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0636   -0.7728    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -1.4518    1.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3728    0.7114   -2.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997   -0.8425   -2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4109   -0.7567   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418    0.5013   -2.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    2.0504   -2.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532    2.1086   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -0.0634    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7467    1.5032   -0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    1.6492    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6912    1.9033   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9722    0.8278   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3628    0.1902   -1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1462   -1.5641   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3782   -1.6546   -0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1364   -1.6755    1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2645    0.1073    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    0.1491    2.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8061   -1.4650    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292    0.5349    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005   -0.7161    2.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0882   -1.7433    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 21 42  1  0
M  END


  Mrv0541 05061312032D          

 21 22  0  0  0  0            999 V2000
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  2  0  0  0  0
 17  8  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 20 17  2  0  0  0  0
 21  1  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040699

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C/C=C/C(=O)N2CCCCC2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c1-21-16-13-14(9-10-15(16)19)7-3-4-8-17(20)18-11-5-2-6-12-18/h3-4,7-10,13,19H,2,5-6,11-12H2,1H3/b7-3-,8-4+

> <INCHI_KEY>
IUGIGWWOEYFTDM-KYPMKJFLSA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.3535

> <EXACT_MASS>
287.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.61648546476323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z)-5-(4-hydroxy-3-methoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
2.692840995333333

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.974268862980006

> <JCHEM_PKA_STRONGEST_BASIC>
2.3682999120090193

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
85.58019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z)-5-(4-hydroxy-3-methoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040699
     RDKit          3D
Feruperine
 42 43  0  0  0  0  0  0  0  0999 V2000
    6.4815   -0.3734   -2.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739   -0.7497   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1990   -0.4203   -0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833    0.2463   -1.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717    0.6073   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674    1.3948   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819    1.4125   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422    0.6625   -0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2878    0.8193   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914    0.0766    0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139   -0.7190    1.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    0.2314    0.9996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2640    1.1212    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0364    0.2953   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3194   -1.0565   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6224   -0.7881    1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -0.5306    1.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8859    0.2407    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182   -0.4440    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0636   -0.7728    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -1.4518    1.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3728    0.7114   -2.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997   -0.8425   -2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4109   -0.7567   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418    0.5013   -2.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    2.0504   -2.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532    2.1086   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -0.0634    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7467    1.5032   -0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    1.6492    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6912    1.9033   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9722    0.8278   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3628    0.1902   -1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1462   -1.5641   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3782   -1.6546   -0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1364   -1.6755    1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2645    0.1073    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    0.1491    2.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8061   -1.4650    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292    0.5349    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005   -0.7161    2.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0882   -1.7433    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 21 42  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      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668   8.470   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    5    6                                                       
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    2   11                                                       
CONECT    6    2   12                                                       
CONECT    7    3   14                                                       
CONECT    8    4   17                                                       
CONECT    9   10   14                                                       
CONECT   10    9   15                                                       
CONECT   11    5   18                                                       
CONECT   12    6   18                                                       
CONECT   13   14   16                                                       
CONECT   14    7    9   13                                                  
CONECT   15   10   16   19                                                  
CONECT   16   13   15   21                                                  
CONECT   17    8   18   20                                                  
CONECT   18   11   12   17                                                  
CONECT   19   15                                                            
CONECT   20   17                                                            
CONECT   21    1   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0040699
HETATM    1  C1  UNL     1       6.482  -0.373  -2.433  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.374  -0.750  -1.076  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.199  -0.420  -0.399  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.183   0.246  -1.030  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.972   0.607  -0.400  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.067   1.395  -1.194  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.782   1.412  -1.035  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.042   0.662  -0.082  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.288   0.819  -0.027  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.091   0.077   0.929  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.514  -0.719   1.705  1.00  0.00           O  
HETATM   12  N1  UNL     1      -3.490   0.231   1.000  1.00  0.00           N  
HETATM   13  C10 UNL     1      -4.264   1.121   0.158  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.036   0.295  -0.867  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.319  -1.056  -0.220  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.622  -0.788   1.235  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.298  -0.531   1.969  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.886   0.241   0.906  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.918  -0.444   1.565  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.064  -0.773   0.923  1.00  0.00           C  
HETATM   21  O3  UNL     1       6.124  -1.452   1.521  1.00  0.00           O  
HETATM   22  H1  UNL     1       6.373   0.711  -2.596  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.600  -0.842  -2.954  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.411  -0.757  -2.899  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.342   0.501  -2.075  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.517   2.050  -2.014  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.253   2.109  -1.750  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.434  -0.063   0.568  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.747   1.503  -0.702  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.986   1.649   0.847  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.691   1.903  -0.334  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.972   0.828  -1.133  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.363   0.190  -1.747  1.00  0.00           H  
HETATM   34  H13 UNL     1      -6.146  -1.564  -0.740  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.378  -1.655  -0.267  1.00  0.00           H  
HETATM   36  H15 UNL     1      -6.136  -1.675   1.660  1.00  0.00           H  
HETATM   37  H16 UNL     1      -6.265   0.107   1.305  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.526   0.149   2.807  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.806  -1.465   2.262  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.029   0.535   1.507  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.801  -0.716   2.605  1.00  0.00           H  
HETATM   42  H21 UNL     1       6.088  -1.743   2.502  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6   18   18
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   29
CONECT   10   11   11   12
CONECT   12   13   17
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   38   39
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   21
CONECT   21   42
END

HMDB0040699
     RDKit          3D
Feruperine
 42 43  0  0  0  0  0  0  0  0999 V2000
    6.4815   -0.3734   -2.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739   -0.7497   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1990   -0.4203   -0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833    0.2463   -1.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717    0.6073   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674    1.3948   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819    1.4125   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422    0.6625   -0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2878    0.8193   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914    0.0766    0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5139   -0.7190    1.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    0.2314    0.9996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2640    1.1212    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0364    0.2953   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3194   -1.0565   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6224   -0.7881    1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -0.5306    1.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8859    0.2407    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182   -0.4440    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0636   -0.7728    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -1.4518    1.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3728    0.7114   -2.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997   -0.8425   -2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4109   -0.7567   -2.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3418    0.5013   -2.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    2.0504   -2.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532    2.1086   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -0.0634    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7467    1.5032   -0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    1.6492    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6912    1.9033   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9722    0.8278   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3628    0.1902   -1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1462   -1.5641   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3782   -1.6546   -0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1364   -1.6755    1.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2645    0.1073    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    0.1491    2.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8061   -1.4650    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292    0.5349    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005   -0.7161    2.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0882   -1.7433    2.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 21 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁NO₃

Average Molecular Weight

287.3535

Monoisotopic Molecular Weight

287.152143543

IUPAC Name

(2E,4Z)-5-(4-hydroxy-3-methoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Traditional Name

(2E,4Z)-5-(4-hydroxy-3-methoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

CAS Registry Number

77795-15-4

SMILES

COC1=C(O)C=CC(\C=C/C=C/C(=O)N2CCCCC2)=C1

InChI Identifier

InChI=1S/C17H21NO3/c1-21-16-13-14(9-10-15(16)19)7-3-4-8-17(20)18-11-5-2-6-12-18/h3-4,7-10,13,19H,2,5-6,11-12H2,1H3/b7-3-,8-4+

InChI Key

IUGIGWWOEYFTDM-KYPMKJFLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
N-acyl-piperidine
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Piperidine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040699)
Cell membrane (HMDB: HMDB0040699)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040699)

Source

Exogenous

Exogenous (HMDB: HMDB0040699)

Food

Food (HMDB: HMDB0040699)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0040699)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040699)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	159 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	42.13 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	3.44	ALOGPS
logP	2.69	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.97	ChemAxon
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.58 m³·mol⁻¹	ChemAxon
Polarizability	31.62 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
DeepCCS	[M+H]+	179.483	30932474
DeepCCS	[M-H]-	177.125	30932474
DeepCCS	[M-2H]-	210.011	30932474
DeepCCS	[M+Na]+	185.576	30932474
AllCCS	[M+H]+	169.4	32859911
AllCCS	[M+H-H2O]+	165.8	32859911
AllCCS	[M+NH4]+	172.7	32859911
AllCCS	[M+Na]+	173.7	32859911
AllCCS	[M-H]-	172.9	32859911
AllCCS	[M+Na-2H]-	173.1	32859911
AllCCS	[M+HCOO]-	173.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.73 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6108 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.53 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2217.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	281.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	235.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	630.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	502.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1296.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	441.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1308.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	417.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	332.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Feruperine	COC1=C(O)C=CC(\C=C/C=C/C(=O)N2CCCCC2)=C1	4167.5	Standard polar	33892256
Feruperine	COC1=C(O)C=CC(\C=C/C=C/C(=O)N2CCCCC2)=C1	2666.3	Standard non polar	33892256
Feruperine	COC1=C(O)C=CC(\C=C/C=C/C(=O)N2CCCCC2)=C1	2924.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Feruperine,1TMS,isomer #1	COC1=CC(/C=C\C=C\C(=O)N2CCCCC2)=CC=C1O[Si](C)(C)C	2834.0	Semi standard non polar	33892256
Feruperine,1TBDMS,isomer #1	COC1=CC(/C=C\C=C\C(=O)N2CCCCC2)=CC=C1O[Si](C)(C)C(C)(C)C	3095.0	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 - Feruperine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0m9r-6790000000-439166b832175737df08	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Feruperine GC-MS (1 TMS) - 70eV, Positive	splash10-007p-5196000000-71230a81fe78b1a8d93e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Feruperine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Feruperine 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 - Feruperine 10V, Positive-QTOF	splash10-000i-2290000000-738774bca6fd78ce8a23	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 20V, Positive-QTOF	splash10-000i-4940000000-46da16377d201b513641	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 40V, Positive-QTOF	splash10-000i-9300000000-b33dc78f09fcca562a42	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 10V, Negative-QTOF	splash10-000i-0090000000-e4cab98af743b6092c74	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 20V, Negative-QTOF	splash10-001r-5290000000-3d0a750290b2587cefb5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 40V, Negative-QTOF	splash10-001i-9200000000-086cdf4a1fb46b30229b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 10V, Negative-QTOF	splash10-000i-0090000000-128f3c74007c67360177	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 20V, Negative-QTOF	splash10-05ai-0890000000-376517a2ad7744a46812	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 40V, Negative-QTOF	splash10-001i-2890000000-4528b8bd16eb46b4c0f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 10V, Positive-QTOF	splash10-052r-0090000000-8f12cd532e9d25797972	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 20V, Positive-QTOF	splash10-0a4r-0490000000-30140f57da3ac340d9e0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruperine 40V, Positive-QTOF	splash10-0019-2910000000-232ab6dfc76b26232fce	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020501

KNApSAcK ID

C00055010

Chemspider ID

30777501

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752909

PDB ID

Not Available

ChEBI ID

174039

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1885581

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 Feruperine (HMDB0040699)

MOL for HMDB0040699 (Feruperine)

3D MOL for HMDB0040699 (Feruperine)

3D SDF for HMDB0040699 (Feruperine)

3D-SDF for HMDB0040699 (Feruperine)

PDB for HMDB0040699 (Feruperine)

3D PDB for HMDB0040699 (Feruperine)

SMILES for HMDB0040699 (Feruperine)

INCHI for HMDB0040699 (Feruperine)

Structure for HMDB0040699 (Feruperine)

3D Structure for HMDB0040699 (Feruperine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra