NP-MRD: Showing NP-Card for Oleacein (NP0048724)

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Record Information

Version

2.0

Created at

2022-03-17 21:01:11 UTC

Updated at

2022-03-17 21:01:11 UTC

NP-MRD ID

NP0048724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oleacein

Description

Oleacein, also known as 3,4-dhpea-eda, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Oleacein is found, on average, in the highest concentration within olives. Oleacein has also been detected, but not quantified in, several different foods, such as fats and oils, fruits, green vegetables, herbs and spices, and tea. Oleacein is found in grandiflorum, Jasminum grandiflorum and Olea lancea. This could make oleacein a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  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>
NP0048724

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

320.3371 Da

Monoisotopic Mass

320.12599 Da

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
grandiflorum	-	KNApSAcK
Jasminum grandiflorum	Plant	KNApSAcK
Olea europaea	FooDB	PHENOL EXPLORER
Olea lancea	LOTUS Database	35616633

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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0037321

DrugBank ID

Not Available

Phenol Explorer Compound ID

681

FoodDB ID

FDB016341

KNApSAcK ID

Not Available

Chemspider ID

18953409

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

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oleacein (NP0048724)

MOL for NP0048724 (Oleacein)

3D MOL for NP0048724 (Oleacein)

3D SDF for NP0048724 (Oleacein)

3D-SDF for NP0048724 (Oleacein)

PDB for NP0048724 (Oleacein)

3D PDB for NP0048724 (Oleacein)

SMILES for NP0048724 (Oleacein)

INCHI for NP0048724 (Oleacein)

Structure for NP0048724 (Oleacein)

3D Structure for NP0048724 (Oleacein)