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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:31:59 UTC

Update Date

2022-03-07 02:53:51 UTC

HMDB ID

HMDB0033771

Secondary Accession Numbers

HMDB33771

Metabolite Identification

Common Name

Cyperine

Description

Cyperine belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. Cyperine has been detected, but not quantified in, root vegetables. This could make cyperine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyperine.

Structure

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

HMDB0033771
     RDKit          3D
Cyperine
 35 36  0  0  0  0  0  0  0  0999 V2000
    5.4924    1.1411    0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7521    0.0234    0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.2321    0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7365   -1.3137    0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419   -1.5344    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404   -2.7421    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305   -0.6861   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -0.9132   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6327   -0.4643   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1611    0.7283   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3814    1.1882   -0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9611    2.4642   -1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0773    0.4684    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -0.7381    0.7437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633   -1.4571    1.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3427   -1.1495    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742    0.4023   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965    1.2710   -2.0868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8529    0.6094   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0860    2.1043    0.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4105    1.1210   -0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698    1.0074    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606   -2.0023    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -2.4600    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -3.5388    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561   -3.1531   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669    1.3308   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836    2.2518   -1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5283    2.9907   -0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616    3.1291   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0231    0.8460    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9292   -2.1446    1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808   -2.0808    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342    2.0666   -2.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040    1.4661   -1.0633 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
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  7 17  1  0
 17 18  1  0
 17 19  2  0
 19  3  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
M  END

  Mrv0541 05061307212D          

 19 20  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 11  4  1  0  0  0  0
 11  7  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18  3  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033771

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C(OC2=CC(C)=CC(O)=C2)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-9-4-11(16)7-13(5-9)19-15-10(2)6-12(18-3)8-14(15)17/h4-8,16-17H,1-3H3

> <INCHI_KEY>
KXXZLMLLYMPYJE-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.32967535831192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-hydroxy-5-methylphenoxy)-5-methoxy-3-methylphenol

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.735573868666666

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.305853214366218

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.451438850446394

> <JCHEM_PKA_STRONGEST_BASIC>
-4.824706899242497

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
72.80620000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyperine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033771
     RDKit          3D
Cyperine
 35 36  0  0  0  0  0  0  0  0999 V2000
    5.4924    1.1411    0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7521    0.0234    0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.2321    0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7365   -1.3137    0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419   -1.5344    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404   -2.7421    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305   -0.6861   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -0.9132   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6327   -0.4643   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1611    0.7283   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3814    1.1882   -0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9611    2.4642   -1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0773    0.4684    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -0.7381    0.7437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633   -1.4571    1.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3427   -1.1495    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742    0.4023   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965    1.2710   -2.0868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8529    0.6094   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0860    2.1043    0.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4105    1.1210   -0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698    1.0074    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606   -2.0023    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -2.4600    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -3.5388    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561   -3.1531   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669    1.3308   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836    2.2518   -1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5283    2.9907   -0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616    3.1291   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0231    0.8460    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9292   -2.1446    1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808   -2.0808    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342    2.0666   -2.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040    1.4661   -1.0633 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
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  7 17  1  0
 17 18  1  0
 17 19  2  0
 19  3  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   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   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   18                                                            
CONECT    4    9   11                                                       
CONECT    5    9   13                                                       
CONECT    6   10   12                                                       
CONECT    7   11   13                                                       
CONECT    8   12   14                                                       
CONECT    9    1    4    5                                                  
CONECT   10    2    6   15                                                  
CONECT   11    4    7   16                                                  
CONECT   12    6    8   18                                                  
CONECT   13    5    7   19                                                  
CONECT   14    8   15   17                                                  
CONECT   15   10   14   19                                                  
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18    3   12                                                       
CONECT   19   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0033771
HETATM    1  C1  UNL     1       5.492   1.141   0.181  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.752   0.023   0.632  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.462  -0.232   0.194  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.737  -1.314   0.627  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.442  -1.534   0.161  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.740  -2.742   0.672  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.830  -0.686  -0.747  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.434  -0.913  -1.191  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.633  -0.464  -0.710  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.161   0.728  -1.169  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.381   1.188  -0.680  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.961   2.464  -1.162  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.077   0.468   0.262  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.569  -0.738   0.744  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.263  -1.457   1.684  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.343  -1.149   0.218  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.574   0.402  -1.177  1.00  0.00           C  
HETATM   18  O4  UNL     1       0.996   1.271  -2.087  1.00  0.00           O  
HETATM   19  C15 UNL     1       2.853   0.609  -0.709  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.086   2.104   0.549  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.411   1.121  -0.943  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.570   1.007   0.391  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.161  -2.002   1.330  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.198  -2.460   1.604  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.499  -3.539   0.857  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.056  -3.153  -0.098  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.667   1.331  -1.909  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.684   2.252  -1.982  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.528   2.991  -0.344  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.162   3.129  -1.523  1.00  0.00           H  
HETATM   31  H12 UNL     1      -5.023   0.846   0.627  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.929  -2.145   1.362  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.981  -2.081   0.599  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.534   2.067  -2.404  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.404   1.466  -1.063  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6    7    7
CONECT    6   24   25   26
CONECT    7    8   17
CONECT    8    9
CONECT    9   10   10   16
CONECT   10   11   27
CONECT   11   12   13   13
CONECT   12   28   29   30
CONECT   13   14   31
CONECT   14   15   16   16
CONECT   15   32
CONECT   16   33
CONECT   17   18   19   19
CONECT   18   34
CONECT   19   35
END

HMDB0033771
     RDKit          3D
Cyperine
 35 36  0  0  0  0  0  0  0  0999 V2000
    5.4924    1.1411    0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7521    0.0234    0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.2321    0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7365   -1.3137    0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419   -1.5344    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404   -2.7421    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305   -0.6861   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4344   -0.9132   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6327   -0.4643   -0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1611    0.7283   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3814    1.1882   -0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9611    2.4642   -1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0773    0.4684    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -0.7381    0.7437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633   -1.4571    1.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3427   -1.1495    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742    0.4023   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965    1.2710   -2.0868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8529    0.6094   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0860    2.1043    0.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4105    1.1210   -0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698    1.0074    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606   -2.0023    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -2.4600    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -3.5388    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561   -3.1531   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669    1.3308   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6836    2.2518   -1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5283    2.9907   -0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616    3.1291   -1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0231    0.8460    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9292   -2.1446    1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808   -2.0808    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342    2.0666   -2.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040    1.4661   -1.0633 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
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  7 17  1  0
 17 18  1  0
 17 19  2  0
 19  3  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3-Hydroxy-5-methylphenoxy)-5-methoxy-3-methylphenol, 9ci	HMDB
Antibiotic LL-V125a	HMDB
LL-V125a	HMDB
Cyperin	MeSH

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

2-(3-hydroxy-5-methylphenoxy)-5-methoxy-3-methylphenol

Traditional Name

cyperine

CAS Registry Number

33716-82-4

SMILES

COC1=CC(O)=C(OC2=CC(C)=CC(O)=C2)C(C)=C1

InChI Identifier

InChI=1S/C15H16O4/c1-9-4-11(16)7-13(5-9)19-15-10(2)6-12(18-3)8-14(15)17/h4-8,16-17H,1-3H3

InChI Key

KXXZLMLLYMPYJE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Diaryl ether
Methoxyphenol
Phenoxy compound
Anisole
M-cresol
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:4041 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033771)
Cell membrane (HMDB: HMDB0033771)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033771)

Source

Exogenous

Exogenous (HMDB: HMDB0033771)

Food

Food (HMDB: HMDB0033771)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB0033771)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033771)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	121.5 - 122.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	3.17	ALOGPS
logP	3.74	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.81 m³·mol⁻¹	ChemAxon
Polarizability	27.33 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]+	164.214	31661259
DarkChem	[M-H]-	165.013	31661259
DeepCCS	[M+H]+	169.705	30932474
DeepCCS	[M-H]-	167.347	30932474
DeepCCS	[M-2H]-	200.234	30932474
DeepCCS	[M+Na]+	175.799	30932474
AllCCS	[M+H]+	159.1	32859911
AllCCS	[M+H-H2O]+	155.3	32859911
AllCCS	[M+NH4]+	162.6	32859911
AllCCS	[M+Na]+	163.6	32859911
AllCCS	[M-H]-	163.4	32859911
AllCCS	[M+Na-2H]-	163.0	32859911
AllCCS	[M+HCOO]-	162.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyperine	COC1=CC(O)=C(OC2=CC(C)=CC(O)=C2)C(C)=C1	3825.1	Standard polar	33892256
Cyperine	COC1=CC(O)=C(OC2=CC(C)=CC(O)=C2)C(C)=C1	2330.7	Standard non polar	33892256
Cyperine	COC1=CC(O)=C(OC2=CC(C)=CC(O)=C2)C(C)=C1	2308.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyperine,1TMS,isomer #1	COC1=CC(C)=C(OC2=CC(C)=CC(O)=C2)C(O[Si](C)(C)C)=C1	2258.8	Semi standard non polar	33892256
Cyperine,1TMS,isomer #2	COC1=CC(C)=C(OC2=CC(C)=CC(O[Si](C)(C)C)=C2)C(O)=C1	2251.8	Semi standard non polar	33892256
Cyperine,2TMS,isomer #1	COC1=CC(C)=C(OC2=CC(C)=CC(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)=C1	2206.9	Semi standard non polar	33892256
Cyperine,1TBDMS,isomer #1	COC1=CC(C)=C(OC2=CC(C)=CC(O)=C2)C(O[Si](C)(C)C(C)(C)C)=C1	2524.8	Semi standard non polar	33892256
Cyperine,1TBDMS,isomer #2	COC1=CC(C)=C(OC2=CC(C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C(O)=C1	2523.2	Semi standard non polar	33892256
Cyperine,2TBDMS,isomer #1	COC1=CC(C)=C(OC2=CC(C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C(O[Si](C)(C)C(C)(C)C)=C1	2716.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyperine GC-MS (Non-derivatized) - 70eV, Positive	splash10-06yk-0790000000-cd0ddee92673e247dc4d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyperine GC-MS (2 TMS) - 70eV, Positive	splash10-0019-2429000000-5f84fce757d927d24623	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyperine 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 - Cyperine 10V, Positive-QTOF	splash10-03di-0090000000-a5ebd52d0b76a952a49b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 20V, Positive-QTOF	splash10-03di-0090000000-596c59f7f394b61ed845	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 40V, Positive-QTOF	splash10-066u-9440000000-7246c5e54db6a42a065a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 10V, Negative-QTOF	splash10-0a4i-0090000000-ad09c26b0d71c125ab18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 20V, Negative-QTOF	splash10-0a4i-0090000000-53eb8089103ce0bf5843	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 40V, Negative-QTOF	splash10-0c00-9830000000-804f793558ad9cdf1f48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 10V, Positive-QTOF	splash10-03di-0590000000-617994041422e09fc0db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 20V, Positive-QTOF	splash10-053j-9800000000-cd898f8845830ad9b2b1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 40V, Positive-QTOF	splash10-0a4i-9100000000-2e06a97f084fd6579ee1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 10V, Negative-QTOF	splash10-0a4i-0290000000-a41e3e1488e3ddd31e80	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 20V, Negative-QTOF	splash10-00e9-9640000000-7f688f58441a5321a029	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperine 40V, Negative-QTOF	splash10-00fv-9600000000-606fa4850fbf7c475d6e	2021-09-25	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182142

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 Cyperine (HMDB0033771)

MOL for HMDB0033771 (Cyperine)

3D MOL for HMDB0033771 (Cyperine)

3D SDF for HMDB0033771 (Cyperine)

3D-SDF for HMDB0033771 (Cyperine)

PDB for HMDB0033771 (Cyperine)

3D PDB for HMDB0033771 (Cyperine)

SMILES for HMDB0033771 (Cyperine)

INCHI for HMDB0033771 (Cyperine)

Structure for HMDB0033771 (Cyperine)

3D Structure for HMDB0033771 (Cyperine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra