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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:16:33 UTC

Update Date

2022-03-07 02:56:42 UTC

HMDB ID

HMDB0040700

Secondary Accession Numbers

HMDB40700

Metabolite Identification

Common Name

Dihydroferuperine

Description

Dihydroferuperine belongs to the class of organic compounds known as n-acylpiperidines. N-acylpiperidines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine. Dihydroferuperine has been detected, but not quantified in, herbs and spices. This could make dihydroferuperine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydroferuperine.

Structure

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

HMDB0040700
     RDKit          3D
Dihydroferuperine
 44 45  0  0  0  0  0  0  0  0999 V2000
    4.6263   -3.3288    3.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6532   -2.0255    3.7281 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563   -1.3330    3.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357   -0.6230    2.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    0.3247    1.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.7843    0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756    1.1266   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    0.9219   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    1.0817   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    1.5555   -2.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328    2.0786   -3.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2527    1.4646   -2.8069 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517    0.8380   -2.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0488   -0.2142   -2.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788    0.2532   -4.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0974    1.7154   -4.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    2.1252   -4.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2766   -0.1605    2.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -0.9107    4.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333   -1.6808    4.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8263   -1.2173    5.6942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7665   -3.8473    3.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -3.1678    2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641   -3.8953    3.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595   -0.4910    1.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6810    1.1104    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    1.5269   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    0.4082    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    0.6272   -0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558    0.3597   -1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    1.6488   -1.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789   -1.1618   -2.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756   -0.4902   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220   -0.3756   -4.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4926    0.1242   -4.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8336    2.3050   -3.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2933    1.9267   -5.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235    3.2319   -3.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662    2.0441   -4.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2442    0.4674    2.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2754   -1.6667    4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.2279    4.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540   -2.7561    4.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4911   -0.4768    5.5763 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  1  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
 19 42  1  0
 20 43  1  0
 21 44  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  1  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  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  2  0  0  0  0
 16 15  1  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>
HMDB0040700

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H23NO3/c1-21-16-13-14(9-10-15(16)19)7-3-4-8-17(20)18-11-5-2-6-12-18/h3-4,7-9,13,15,19H,2,5-6,10-12H2,1H3/b7-3-,8-4+

> <INCHI_KEY>
PUYWOMGLUNDEFM-KYPMKJFLSA-N

> <FORMULA>
C17H23NO3

> <MOLECULAR_WEIGHT>
289.3694

> <EXACT_MASS>
289.167793607

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.36352779267926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
0.9828097489999992

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.860403444642202

> <JCHEM_PKA_STRONGEST_BASIC>
2.368305299111539

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
88.3171

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040700
     RDKit          3D
Dihydroferuperine
 44 45  0  0  0  0  0  0  0  0999 V2000
    4.6263   -3.3288    3.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6532   -2.0255    3.7281 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563   -1.3330    3.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357   -0.6230    2.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    0.3247    1.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.7843    0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756    1.1266   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    0.9219   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    1.0817   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    1.5555   -2.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328    2.0786   -3.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2527    1.4646   -2.8069 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517    0.8380   -2.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0488   -0.2142   -2.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788    0.2532   -4.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0974    1.7154   -4.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    2.1252   -4.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2766   -0.1605    2.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -0.9107    4.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333   -1.6808    4.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8263   -1.2173    5.6942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7665   -3.8473    3.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -3.1678    2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641   -3.8953    3.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595   -0.4910    1.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6810    1.1104    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    1.5269   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    0.4082    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    0.6272   -0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558    0.3597   -1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    1.6488   -1.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789   -1.1618   -2.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756   -0.4902   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220   -0.3756   -4.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4926    0.1242   -4.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8336    2.3050   -3.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2933    1.9267   -5.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235    3.2319   -3.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662    2.0441   -4.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2442    0.4674    2.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2754   -1.6667    4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.2279    4.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540   -2.7561    4.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4911   -0.4768    5.5763 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  1  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
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -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    HMDB0040700
HETATM    1  C1  UNL     1       4.626  -3.329   3.133  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.653  -2.026   3.728  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.356  -1.333   3.433  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.336  -0.623   2.444  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.972   0.325   1.828  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.631   0.784   0.827  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.976   1.127  -0.385  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.604   0.922  -0.465  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.397   1.082  -1.235  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.838   1.556  -2.470  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.133   2.079  -3.362  1.00  0.00           O  
HETATM   12  N1  UNL     1      -2.253   1.465  -2.807  1.00  0.00           N  
HETATM   13  C10 UNL     1      -3.252   0.838  -2.006  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.049  -0.214  -2.782  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.379   0.253  -4.158  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.097   1.715  -4.374  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.686   2.125  -4.002  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.277  -0.161   2.884  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.125  -0.911   4.027  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.333  -1.681   4.454  1.00  0.00           C  
HETATM   21  O3  UNL     1       2.826  -1.217   5.694  1.00  0.00           O  
HETATM   22  H1  UNL     1       3.766  -3.847   3.595  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.453  -3.168   2.052  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.564  -3.895   3.315  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.160  -0.491   1.780  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.681   1.110   0.608  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.604   1.527  -1.162  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.173   0.408   0.468  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.282   0.627  -0.623  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.956   0.360  -1.094  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.034   1.649  -1.814  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.479  -1.162  -2.870  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.976  -0.490  -2.225  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.922  -0.376  -4.949  1.00  0.00           H  
HETATM   35  H14 UNL     1      -5.493   0.124  -4.308  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.834   2.305  -3.792  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.293   1.927  -5.428  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.724   3.232  -3.730  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.066   2.044  -4.881  1.00  0.00           H  
HETATM   40  H19 UNL     1       0.244   0.467   2.679  1.00  0.00           H  
HETATM   41  H20 UNL     1       0.275  -1.667   4.002  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.860  -0.228   4.941  1.00  0.00           H  
HETATM   43  H22 UNL     1       2.154  -2.756   4.480  1.00  0.00           H  
HETATM   44  H23 UNL     1       3.491  -0.477   5.576  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   41   42
CONECT   20   21   43
CONECT   21   44
END

HMDB0040700
     RDKit          3D
Dihydroferuperine
 44 45  0  0  0  0  0  0  0  0999 V2000
    4.6263   -3.3288    3.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6532   -2.0255    3.7281 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563   -1.3330    3.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357   -0.6230    2.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    0.3247    1.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.7843    0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756    1.1266   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    0.9219   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    1.0817   -1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    1.5555   -2.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328    2.0786   -3.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2527    1.4646   -2.8069 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517    0.8380   -2.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0488   -0.2142   -2.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788    0.2532   -4.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0974    1.7154   -4.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6863    2.1252   -4.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2766   -0.1605    2.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -0.9107    4.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333   -1.6808    4.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8263   -1.2173    5.6942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7665   -3.8473    3.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4528   -3.1678    2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641   -3.8953    3.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595   -0.4910    1.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6810    1.1104    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    1.5269   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730    0.4082    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    0.6272   -0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9558    0.3597   -1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    1.6488   -1.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789   -1.1618   -2.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756   -0.4902   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220   -0.3756   -4.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4926    0.1242   -4.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8336    2.3050   -3.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2933    1.9267   -5.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235    3.2319   -3.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662    2.0441   -4.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2442    0.4674    2.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2754   -1.6667    4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.2279    4.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540   -2.7561    4.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4911   -0.4768    5.5763 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  1  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
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₂₃NO₃

Average Molecular Weight

289.3694

Monoisotopic Molecular Weight

289.167793607

IUPAC Name

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

Traditional Name

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

CAS Registry Number

77795-17-6

SMILES

COC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O

InChI Identifier

InChI=1S/C17H23NO3/c1-21-16-13-14(9-10-15(16)19)7-3-4-8-17(20)18-11-5-2-6-12-18/h3-4,7-9,13,15,19H,2,5-6,10-12H2,1H3/b7-3-,8-4+

InChI Key

PUYWOMGLUNDEFM-KYPMKJFLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylpiperidines. N-acylpiperidines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

N-acylpiperidines

Direct Parent

N-acylpiperidines

Alternative Parents

Substituents

N-acyl-piperidine
Tertiary carboxylic acid amide
Carboxamide group
Secondary alcohol
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040700)
Cytoplasm (HMDB: HMDB0040700)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040700)

Source

Exogenous

Food

Food (HMDB: HMDB0040700)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0040700)

Not Available

Nutrient (HMDB: HMDB0040700)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	78 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	213.8 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	0.38 g/L	ALOGPS
logP	2.43	ALOGPS
logP	0.98	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.86	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	88.32 m³·mol⁻¹	ChemAxon
Polarizability	32.36 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]+	172.414	31661259
DarkChem	[M-H]-	168.477	31661259
DeepCCS	[M+H]+	174.064	30932474
DeepCCS	[M-H]-	171.706	30932474
DeepCCS	[M-2H]-	204.592	30932474
DeepCCS	[M+Na]+	180.157	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.2	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.8	32859911
AllCCS	[M-H]-	173.8	32859911
AllCCS	[M+Na-2H]-	174.1	32859911
AllCCS	[M+HCOO]-	174.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroferuperine	COC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O	4259.7	Standard polar	33892256
Dihydroferuperine	COC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O	2554.8	Standard non polar	33892256
Dihydroferuperine	COC1=CC(\C=C/C=C/C(=O)N2CCCCC2)=CCC1O	2967.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroferuperine,1TMS,isomer #1	COC1=CC(/C=C\C=C\C(=O)N2CCCCC2)=CCC1O[Si](C)(C)C	2745.2	Semi standard non polar	33892256
Dihydroferuperine,1TBDMS,isomer #1	COC1=CC(/C=C\C=C\C(=O)N2CCCCC2)=CCC1O[Si](C)(C)C(C)(C)C	2985.8	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 - Dihydroferuperine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0l4i-2390000000-47fcff7208568c1b569f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroferuperine GC-MS (1 TMS) - 70eV, Positive	splash10-0101-7194000000-7d086cdfeb655b8f3b88	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroferuperine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroferuperine 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 - Dihydroferuperine 10V, Positive-QTOF	splash10-0006-2390000000-11a16cf77db548194d05	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 20V, Positive-QTOF	splash10-000i-5940000000-d3e419efb5a33d9b09a2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 40V, Positive-QTOF	splash10-000i-9100000000-262c12b98e7542987a19	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 10V, Negative-QTOF	splash10-000i-0090000000-06ec6073301dbae8a442	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 20V, Negative-QTOF	splash10-001r-5290000000-2b699288a58d25ec6f3c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 40V, Negative-QTOF	splash10-001i-9200000000-0f2e4bc015d350e1d071	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 10V, Negative-QTOF	splash10-000i-0090000000-1f5244541851cecc3419	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 20V, Negative-QTOF	splash10-0079-0980000000-eeadcf89baeecc08a053	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 40V, Negative-QTOF	splash10-0079-3890000000-b69a74849a0ae1b5a7b6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 10V, Positive-QTOF	splash10-0006-0090000000-23ed04513d8f5d80a7a7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 20V, Positive-QTOF	splash10-006x-0290000000-8bf718fc0ca406ee8493	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferuperine 40V, Positive-QTOF	splash10-0f79-4960000000-4609a34e11d5d896c368	2021-09-24	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

FDB020502

KNApSAcK ID

C00055010

Chemspider ID

35015006

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752910

PDB ID

Not Available

ChEBI ID

174060

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1885591

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 Dihydroferuperine (HMDB0040700)

MOL for HMDB0040700 (Dihydroferuperine)

3D MOL for HMDB0040700 (Dihydroferuperine)

3D SDF for HMDB0040700 (Dihydroferuperine)

3D-SDF for HMDB0040700 (Dihydroferuperine)

PDB for HMDB0040700 (Dihydroferuperine)

3D PDB for HMDB0040700 (Dihydroferuperine)

SMILES for HMDB0040700 (Dihydroferuperine)

INCHI for HMDB0040700 (Dihydroferuperine)

Structure for HMDB0040700 (Dihydroferuperine)

3D Structure for HMDB0040700 (Dihydroferuperine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra