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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:33:33 UTC

Update Date

2022-03-07 02:55:16 UTC

HMDB ID

HMDB0037321

Secondary Accession Numbers

HMDB37321

Metabolite Identification

Common Name

Oleacein

Description

Oleacein belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group. Oleacein is found, on average, in the highest concentration within olives (Olea europaea). Oleacein has also been detected, but not quantified in, several different foods, such as green tea, fruits, black tea, herbal tea, and green vegetables. This could make oleacein a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Oleacein.

Structure

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

HMDB0037321
     RDKit          3D
Oleacein
 43 43  0  0  0  0  0  0  0  0999 V2000
    5.0629    2.3744    1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369    1.4384    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    0.5684    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    0.5188    2.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331    1.2795    3.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7067   -0.3681    0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405   -0.3760   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113    0.8497   -1.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241    0.8333   -3.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.0878    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3746   -0.9358   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4409   -0.9366   -1.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -1.8272    0.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -2.6126   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -1.9051   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -1.0046   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4408   -1.5330   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4209   -0.7885   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1977    0.5396    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1860    1.3336    0.8090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9832    1.0983   -0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7365    2.4502    0.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0081    0.3135   -0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    3.1061    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7468    3.0045    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252    1.9011    2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    1.4793   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298   -0.1832    3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -1.3807    0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527   -1.2038   -1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -0.6854   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790    1.7534   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925   -0.2451    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    0.9899    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7606   -3.3838   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0351   -3.2257    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005   -1.3256   -2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -2.6907   -2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557   -2.5894   -0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3819   -1.2052    0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0796    0.9507    1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    2.9728    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565    0.7381   -0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  1  0
M  END


  Mrv1652309261714162D          

 24 24  0  0  0  0            999 V2000
   -3.0492    3.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    3.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7019    5.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2420    6.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3517    4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2391    5.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415    5.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6217    6.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8918    5.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    3.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589    4.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9720    6.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618    6.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913    4.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    5.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188    2.6113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5119    7.4446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8918    7.7564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787    5.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    4.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792    4.4823    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 12  3  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  2  2  0  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  1  0  0  0  0
 18  7  2  0  0  0  0
 19 11  2  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  2  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
 24  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037321

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(C)=C(\C=O)C(CC=O)CC(=O)OCCC1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O6/c1-2-13(11-19)14(5-7-18)10-17(22)23-8-6-12-3-4-15(20)16(21)9-12/h2-4,7,9,11,14,20-21H,5-6,8,10H2,1H3/b13-2+

> <INCHI_KEY>
XLPXUPOZUYGVPD-XNJYKOPJSA-N

> <FORMULA>
C17H20O6

> <MOLECULAR_WEIGHT>
320.3371

> <EXACT_MASS>
320.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.15328801909256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)ethyl (4Z)-4-formyl-3-(2-oxoethyl)hex-4-enoate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
1.5300395683333332

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.734198771017844

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.284725821962894

> <JCHEM_PKA_STRONGEST_BASIC>
-4.405819355400649

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
85.25209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)ethyl (4Z)-4-formyl-3-(2-oxoethyl)hex-4-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037321
     RDKit          3D
Oleacein
 43 43  0  0  0  0  0  0  0  0999 V2000
    5.0629    2.3744    1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369    1.4384    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    0.5684    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    0.5188    2.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331    1.2795    3.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7067   -0.3681    0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405   -0.3760   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113    0.8497   -1.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241    0.8333   -3.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.0878    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3746   -0.9358   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4409   -0.9366   -1.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -1.8272    0.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -2.6126   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -1.9051   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -1.0046   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4408   -1.5330   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4209   -0.7885   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1977    0.5396    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1860    1.3336    0.8090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9832    1.0983   -0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7365    2.4502    0.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0081    0.3135   -0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    3.1061    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7468    3.0045    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252    1.9011    2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    1.4793   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298   -0.1832    3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -1.3807    0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527   -1.2038   -1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -0.6854   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790    1.7534   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925   -0.2451    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    0.9899    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7606   -3.3838   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0351   -3.2257    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005   -1.3256   -2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -2.6907   -2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557   -2.5894   -0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3819   -1.2052    0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0796    0.9507    1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    2.9728    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565    0.7381   -0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 26-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-SEP-17         0                                  
HETATM    1  C   UNK     0      -5.692   5.748   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.684   6.912   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.910  10.113   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.918  11.277   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.390   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.180   9.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.877   9.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.894  11.859   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.651   7.494   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   5.166   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.398  10.404   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.171   6.621   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.163   7.785   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.414  12.732   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.902  13.023   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.357   8.658   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.684  10.986   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.155   4.874   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.422  13.897   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.398  14.479   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.147  10.113   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.869   8.367   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      -5.188   8.367   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1   13   24                                                  
CONECT    3    4   12                                                       
CONECT    4    3   15                                                       
CONECT    5    7   14                                                       
CONECT    6    8   12                                                       
CONECT    7    5   18                                                       
CONECT    8    6   23                                                       
CONECT    9   12   16                                                       
CONECT   10   14   17                                                       
CONECT   11   13   19                                                       
CONECT   12    3    6    9                                                  
CONECT   13    2   11   14                                                  
CONECT   14    5   10   13                                                  
CONECT   15    4   16   20                                                  
CONECT   16    9   15   21                                                  
CONECT   17   10   22   23                                                  
CONECT   18    7                                                            
CONECT   19   11                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    8   17                                                       
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0037321
HETATM    1  C1  UNL     1       5.063   2.374   1.701  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.337   1.438   0.808  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.446   0.568   1.221  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.153   0.519   2.645  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.733   1.280   3.436  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.707  -0.368   0.312  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.140  -0.376  -1.093  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.011   0.850  -1.877  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.424   0.833  -3.025  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.210  -0.088   0.482  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.375  -0.936  -0.350  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.441  -0.937  -1.603  1.00  0.00           O  
HETATM   13  O4  UNL     1      -0.580  -1.827   0.183  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.353  -2.613  -0.652  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.227  -1.905  -1.631  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.215  -1.005  -0.996  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.441  -1.533  -0.661  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.421  -0.789  -0.073  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.198   0.540   0.204  1.00  0.00           C  
HETATM   20  O5  UNL     1      -6.186   1.334   0.809  1.00  0.00           O  
HETATM   21  C16 UNL     1      -3.983   1.098  -0.117  1.00  0.00           C  
HETATM   22  O6  UNL     1      -3.736   2.450   0.158  1.00  0.00           O  
HETATM   23  C17 UNL     1      -3.008   0.314  -0.714  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.423   3.106   2.210  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.747   3.005   1.057  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.725   1.901   2.427  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.570   1.479  -0.224  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.430  -0.183   3.009  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.858  -1.381   0.730  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.653  -1.204  -1.634  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.230  -0.685  -1.077  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.579   1.753  -1.508  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.993  -0.245   1.569  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.049   0.990   0.284  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.761  -3.384  -1.214  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.035  -3.226   0.000  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.700  -1.326  -2.405  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.796  -2.691  -2.182  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.656  -2.589  -0.868  1.00  0.00           H  
HETATM   40  H17 UNL     1      -6.382  -1.205   0.187  1.00  0.00           H  
HETATM   41  H18 UNL     1      -7.080   0.951   1.053  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.481   2.973   0.592  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.056   0.738  -0.971  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   27
CONECT    3    4    6
CONECT    4    5    5   28
CONECT    6    7   10   29
CONECT    7    8   30   31
CONECT    8    9    9   32
CONECT   10   11   33   34
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   17   17   23
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   21
CONECT   20   41
CONECT   21   22   23   23
CONECT   22   42
CONECT   23   43
END

HMDB0037321
     RDKit          3D
Oleacein
 43 43  0  0  0  0  0  0  0  0999 V2000
    5.0629    2.3744    1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369    1.4384    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456    0.5684    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    0.5188    2.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331    1.2795    3.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7067   -0.3681    0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405   -0.3760   -1.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113    0.8497   -1.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241    0.8333   -3.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098   -0.0878    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3746   -0.9358   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4409   -0.9366   -1.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -1.8272    0.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -2.6126   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -1.9051   -1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -1.0046   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4408   -1.5330   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4209   -0.7885   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1977    0.5396    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1860    1.3336    0.8090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9832    1.0983   -0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7365    2.4502    0.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0081    0.3135   -0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    3.1061    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7468    3.0045    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252    1.9011    2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    1.4793   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298   -0.1832    3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -1.3807    0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527   -1.2038   -1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -0.6854   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790    1.7534   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925   -0.2451    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    0.9899    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7606   -3.3838   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0351   -3.2257    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005   -1.3256   -2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -2.6907   -2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557   -2.5894   -0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3819   -1.2052    0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0796    0.9507    1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4807    2.9728    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565    0.7381   -0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 22 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)ethyl 4-formyl-3-formylmethyl-4-hexenoate	HMDB
3,4-DHPEA-eda	HMDB
2-(3,4-Dihydroxyphenyl)ethyl (4Z)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid	Generator
Oleacein	MeSH

Chemical Formula

C₁₇H₂₀O₆

Average Molecular Weight

320.3371

Monoisotopic Molecular Weight

320.125988372

IUPAC Name

2-(3,4-dihydroxyphenyl)ethyl (4Z)-4-formyl-3-(2-oxoethyl)hex-4-enoate

Traditional Name

2-(3,4-dihydroxyphenyl)ethyl (4Z)-4-formyl-3-(2-oxoethyl)hex-4-enoate

CAS Registry Number

149183-75-5

SMILES

[H]\C(C)=C(\C=O)C(CC=O)CC(=O)OCCC1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C17H20O6/c1-2-13(11-19)14(5-7-18)10-17(22)23-8-6-12-3-4-15(20)16(21)9-12/h2-4,7,9,11,14,20-21H,5-6,8,10H2,1H3/b13-2+

InChI Key

XLPXUPOZUYGVPD-XNJYKOPJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Tyrosols and derivatives

Direct Parent

Tyrosols and derivatives

Alternative Parents

Substituents

Tyrosol derivative
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Alpha,beta-unsaturated aldehyde
Alpha-hydrogen aldehyde
Enal
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Aldehyde
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037321)

Cellular substructure

Membrane (HMDB: HMDB0037321)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037321)

Source

Exogenous

Food

Food (HMDB: HMDB0037321)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Oilseed crop

Olive oil (FooDB: FOOD00909)

Fruit

Fruits (FooDB: FOOD00871)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0037321)

Not Available

Nutrient (HMDB: HMDB0037321)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	954.7 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	0.042 g/L	ALOGPS
logP	2.71	ALOGPS
logP	1.53	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	85.25 m³·mol⁻¹	ChemAxon
Polarizability	33.15 Å³	ChemAxon
Number of Rings	1	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]+	174.539	31661259
DarkChem	[M-H]-	173.764	31661259
DeepCCS	[M+H]+	181.919	30932474
DeepCCS	[M-H]-	179.561	30932474
DeepCCS	[M-2H]-	213.705	30932474
DeepCCS	[M+Na]+	189.058	30932474
AllCCS	[M+H]+	174.5	32859911
AllCCS	[M+H-H2O]+	171.7	32859911
AllCCS	[M+NH4]+	177.1	32859911
AllCCS	[M+Na]+	177.9	32859911
AllCCS	[M-H]-	175.3	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oleacein	[H]\C(C)=C(\C=O)C(CC=O)CC(=O)OCCC1=CC(O)=C(O)C=C1	4380.2	Standard polar	33892256
Oleacein	[H]\C(C)=C(\C=O)C(CC=O)CC(=O)OCCC1=CC(O)=C(O)C=C1	2517.2	Standard non polar	33892256
Oleacein	[H]\C(C)=C(\C=O)C(CC=O)CC(=O)OCCC1=CC(O)=C(O)C=C1	2596.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oleacein,1TMS,isomer #1	C/C=C(\C=O)C(CC=O)CC(=O)OCCC1=CC=C(O)C(O[Si](C)(C)C)=C1	2795.8	Semi standard non polar	33892256
Oleacein,1TMS,isomer #2	C/C=C(\C=O)C(CC=O)CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C(O)=C1	2790.3	Semi standard non polar	33892256
Oleacein,1TMS,isomer #3	C/C=C(\C=O)C(C=CO[Si](C)(C)C)CC(=O)OCCC1=CC=C(O)C(O)=C1	2904.8	Semi standard non polar	33892256
Oleacein,2TMS,isomer #1	C/C=C(\C=O)C(CC=O)CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2834.8	Semi standard non polar	33892256
Oleacein,2TMS,isomer #2	C/C=C(\C=O)C(C=CO[Si](C)(C)C)CC(=O)OCCC1=CC=C(O)C(O[Si](C)(C)C)=C1	2867.5	Semi standard non polar	33892256
Oleacein,2TMS,isomer #3	C/C=C(\C=O)C(C=CO[Si](C)(C)C)CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C(O)=C1	2876.3	Semi standard non polar	33892256
Oleacein,3TMS,isomer #1	C/C=C(\C=O)C(C=CO[Si](C)(C)C)CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2905.6	Semi standard non polar	33892256
Oleacein,3TMS,isomer #1	C/C=C(\C=O)C(C=CO[Si](C)(C)C)CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2782.1	Standard non polar	33892256
Oleacein,1TBDMS,isomer #1	C/C=C(\C=O)C(CC=O)CC(=O)OCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	3046.0	Semi standard non polar	33892256
Oleacein,1TBDMS,isomer #2	C/C=C(\C=O)C(CC=O)CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	3043.1	Semi standard non polar	33892256
Oleacein,1TBDMS,isomer #3	C/C=C(\C=O)C(C=CO[Si](C)(C)C(C)(C)C)CC(=O)OCCC1=CC=C(O)C(O)=C1	3147.5	Semi standard non polar	33892256
Oleacein,2TBDMS,isomer #1	C/C=C(\C=O)C(CC=O)CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3277.7	Semi standard non polar	33892256
Oleacein,2TBDMS,isomer #2	C/C=C(\C=O)C(C=CO[Si](C)(C)C(C)(C)C)CC(=O)OCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	3325.2	Semi standard non polar	33892256
Oleacein,2TBDMS,isomer #3	C/C=C(\C=O)C(C=CO[Si](C)(C)C(C)(C)C)CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	3332.8	Semi standard non polar	33892256
Oleacein,3TBDMS,isomer #1	C/C=C(\C=O)C(C=CO[Si](C)(C)C(C)(C)C)CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3547.8	Semi standard non polar	33892256
Oleacein,3TBDMS,isomer #1	C/C=C(\C=O)C(C=CO[Si](C)(C)C(C)(C)C)CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3359.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oleacein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-1910000000-ebd6d13f446f3ae99933	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleacein GC-MS (2 TMS) - 70eV, Positive	splash10-015i-3971400000-f2cdf2c17b3d4ba9ae5d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleacein GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleacein 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 - Oleacein 10V, Positive-QTOF	splash10-00dr-0927000000-1bbeacdc4a84a997ecec	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 20V, Positive-QTOF	splash10-000i-1900000000-09f08428e08820c0c860	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 40V, Positive-QTOF	splash10-000i-5900000000-3b77b522648e30246fc9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 10V, Negative-QTOF	splash10-014i-0906000000-613a49de258c29ded2dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 20V, Negative-QTOF	splash10-0159-1901000000-64bb83519c194bcafe34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 40V, Negative-QTOF	splash10-00y3-3900000000-1db87c6af7c0531e4e7d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 10V, Negative-QTOF	splash10-03di-0290000000-b50992a72d18c6d0133b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 20V, Negative-QTOF	splash10-01p9-1950000000-c08f6bee6d619165242d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 40V, Negative-QTOF	splash10-00dl-5900000000-6de8ee7f5743684718d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 10V, Positive-QTOF	splash10-002u-0590000000-e2aaba707a02de378eeb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 20V, Positive-QTOF	splash10-000i-0960000000-179ad1aec11a3a143c1d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleacein 40V, Positive-QTOF	splash10-000i-1900000000-fe322391b1fa2a501ac4	2021-09-23	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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18684078

PDB ID

Not Available

ChEBI ID

175090

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859821

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 Oleacein (HMDB0037321)

MOL for HMDB0037321 (Oleacein)

3D MOL for HMDB0037321 (Oleacein)

3D SDF for HMDB0037321 (Oleacein)

3D-SDF for HMDB0037321 (Oleacein)

PDB for HMDB0037321 (Oleacein)

3D PDB for HMDB0037321 (Oleacein)

SMILES for HMDB0037321 (Oleacein)

INCHI for HMDB0037321 (Oleacein)

Structure for HMDB0037321 (Oleacein)

3D Structure for HMDB0037321 (Oleacein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra