NP-MRD: Showing NP-Card for Oleocanthal (NP0137303)

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Record Information

Version

2.0

Created at

2022-05-30 16:48:19 UTC

Updated at

2022-05-30 16:48:19 UTC

NP-MRD ID

NP0137303

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oleocanthal

Description

Oleocanthal 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. Oleocanthal was first documented in 2022 (PMID: 35630786). Based on a literature review a small amount of articles have been published on Oleocanthal (PMID: 35564077) (PMID: 35548334) (PMID: 35532254).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
   -4.3145    2.6703   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415    1.6588   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    0.5106    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    0.2048    0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5830    0.9865    0.9855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917   -0.4974    0.2593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7173   -1.7271   -0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9192   -2.3755    0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9923   -2.3338   -0.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517    0.0907   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0314   -0.9388   -0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1731   -1.7184   -1.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386   -1.0142    0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590   -1.9678    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9179   -1.8191   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6186   -0.5322   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7526   -0.3563    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4437    0.8374    0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9754    1.9272   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6829    3.1042    0.0471 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    1.7676   -0.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695    0.5478   -0.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5483    2.9419    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145    3.5737   -1.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2141    2.2381   -0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3276    1.8946   -0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150   -0.7068    1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238   -0.6844    1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680   -2.4538   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426   -1.4609   -1.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9545   -2.9204    0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560    0.9695    0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339    0.3703   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2528   -2.0781    1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618   -2.9637    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6528   -2.6597   -0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505   -1.9056   -1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857   -1.2298    1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3352    0.9515    1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4717    3.9546   -0.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    2.6389   -1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2939    0.5047   -1.4836 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  2  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
M  END


  Mrv1652305302218482D          

 22 22  0  0  0  0            999 V2000
    3.0323   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922   -2.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221   -3.2448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -2.9329    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
    4.1124   -4.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -5.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -3.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -4.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -3.2448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -3.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -4.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032   -4.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -4.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -5.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5133   -6.2071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -5.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -5.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137303

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C=O)C(CC=O)CC(=O)OCCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O5/c1-2-14(12-19)15(7-9-18)11-17(21)22-10-8-13-3-5-16(20)6-4-13/h2-6,9,12,15,20H,7-8,10-11H2,1H3

> <INCHI_KEY>
VPOVFCBNUOUZGG-UHFFFAOYSA-N

> <FORMULA>
C17H20O5

> <MOLECULAR_WEIGHT>
304.342

> <EXACT_MASS>
304.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.838104230832972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)ethyl 4-formyl-3-(2-oxoethyl)hex-4-enoate

> <JCHEM_LOGP>
1.8336048900000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.709917989493523

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.503740717670135

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4058193553500145

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
83.27120000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
oleocanthal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-22         0                                  
HETATM    1  C   UNK     0       5.660  -1.691   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.856   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.164  -4.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.652  -4.602   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.148  -6.057   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.172  -5.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.677  -8.094   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.172  -9.549   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.685  -5.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.693  -6.348   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.189  -7.803   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.205  -6.057   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.213  -7.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.726  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.734  -8.094   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.246  -7.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.254  -8.967   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.750 -10.422   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.758 -11.587   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      15.238 -10.713   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.230  -9.549   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-(4-Hydroxyphenyl)ethyl 4-formyl-3-(2-oxoethyl)hex-4-enoic acid	HMDB

Chemical Formula

C₁₇H₂₀O₅

Average Mass

304.3420 Da

Monoisotopic Mass

304.13107 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC=C(C=O)C(CC=O)CC(=O)OCCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C17H20O5/c1-2-14(12-19)15(7-9-18)11-17(21)22-10-8-13-3-5-16(20)6-4-13/h2-6,9,12,15,20H,7-8,10-11H2,1H3

InChI Key

VPOVFCBNUOUZGG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

External Links

HMDB ID

HMDB0255942

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00053596

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oleocanthal

METLIN ID

Not Available

PubChem Compound

73042908

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kugic A, Dabelic S, Brala CJ, Dabelic N, Barbaric M: Extra Virgin Olive Oil Secoiridoids Modulate the Metabolic Activity of Dacarbazine Pre-Treated and Treatment-Naive Melanoma Cells. Molecules. 2022 May 21;27(10). pii: molecules27103310. doi: 10.3390/molecules27103310. [PubMed:35630786 ]
Esposito Salsano J, Digiacomo M, Cuffaro D, Bertini S, Macchia M: Content Variations in Oleocanthalic Acid and Other Phenolic Compounds in Extra-Virgin Olive Oil during Storage. Foods. 2022 May 6;11(9). pii: foods11091354. doi: 10.3390/foods11091354. [PubMed:35564077 ]
Di Pietro M, Filardo S, Mattioli R, Francioso A, Raponi G, Mosca L, Sessa R: Extra Virgin Olive Oil-Based Green Formulations With Promising Antimicrobial Activity Against Drug-Resistant Isolates. Front Pharmacol. 2022 Apr 25;13:885735. doi: 10.3389/fphar.2022.885735. eCollection 2022. [PubMed:35548334 ]
Villalobos-Nova K, Monroy-Moya S, Maulen-Penaloza J, Maia Pinto GC, Cornejo A: Bringing the Spotlight to tau and TDP-43 in Frontotemporal Dementia: A Review of Promising Chemical Compounds. Curr Med Chem. 2022 May 8. pii: CMC-EPUB-123180. doi: 10.2174/0929867329666220508175340. [PubMed:35532254 ]

Showing NP-Card for Oleocanthal (NP0137303)

MOL for NP0137303 (Oleocanthal)

3D MOL for NP0137303 (Oleocanthal)

3D SDF for NP0137303 (Oleocanthal)

3D-SDF for NP0137303 (Oleocanthal)

PDB for NP0137303 (Oleocanthal)

3D PDB for NP0137303 (Oleocanthal)

SMILES for NP0137303 (Oleocanthal)

INCHI for NP0137303 (Oleocanthal)

Structure for NP0137303 (Oleocanthal)

3D Structure for NP0137303 (Oleocanthal)