NP-MRD: Showing NP-Card for Ovalitenone (NP0054716)

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Record Information

Version

2.0

Created at

2022-04-28 00:58:57 UTC

Updated at

2022-04-28 00:58:57 UTC

NP-MRD ID

NP0054716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ovalitenone

Description

Ovalitenone, also known as glabra I, belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, ovalitenone is considered to be a flavonoid lipid molecule. Ovalitenone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Ovalitenone has been detected, but not quantified in, fruits. Ovalitenone is found in Dahlstedtia pinnata, Derris ovalifolia, Milletia ovalifolia, Millettia erythrocalyx, Millettia ovalifolia, Millettia peguensis, Millettia pinnata and Rhus chinensis . This could make ovalitenone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
   -2.5188   -1.4736   -1.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0995   -0.2538   -1.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921    0.2039   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009   -0.0154    1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7479   -0.7174    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3215   -0.8590    2.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0226   -1.2519    0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421   -1.7924    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050   -2.9230    1.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -1.1782    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747   -1.7652    0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -1.1931    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1281    0.0267    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9984    0.6446   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7493    0.0353   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3594    1.8613   -1.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7595    1.9392   -1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2277    0.8297   -0.2959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6233    0.5090    2.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7927    1.2218    2.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794    1.4399    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4668    2.0729    0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6426    2.0249   -0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981    1.3150   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822    0.9338   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4285   -1.3633   -2.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995   -1.8049   -2.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7495   -2.2256   -1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5285   -2.1780   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.5422   -0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7106   -2.7337    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9224   -1.6609    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029    0.5931   -0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2018    1.8661   -2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1192    2.8530   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924    0.3584    3.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3028    1.6440    2.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4715    2.4761   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4257    1.0829   -2.3726 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 19  1  0
 19 20  2  0
 20 21  1  0
 21 25  2  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 15  2  0
 15 14  1  0
 14 13  2  0
 13 18  1  0
 18 17  1  0
 17 16  1  0
 13 12  1  0
 12 11  2  0
 25  3  1  0
 11 10  1  0
 22 21  1  0
 16 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 19 36  1  0
 20 37  1  0
 24 39  1  0
 23 38  1  0
  7 29  1  0
  7 30  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 12 32  1  0
 11 31  1  0
M  END


  Mrv0541 05061305232D          

 25 28  0  0  0  0            999 V2000
    2.0701    6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    6.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910    6.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7718    5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8266    6.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2869    5.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2869    4.5680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
 11  2  1  0  0  0  0
 11  8  2  0  0  0  0
 12  3  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  5  1  0  0  0  0
 16 13  2  0  0  0  0
 17  4  1  0  0  0  0
 18  8  1  0  0  0  0
 18 17  2  0  0  0  0
 19 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  2  0  0  0  0
 22  1  1  0  0  0  0
 22 19  1  0  0  0  0
 23  7  1  0  0  0  0
 23 16  1  0  0  0  0
 24 10  1  0  0  0  0
 24 17  1  0  0  0  0
 25 10  1  0  0  0  0
 25 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=CC2=C1C=CO2)C(=O)CC(=O)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O6/c1-22-19-12(3-5-16-13(19)6-7-23-16)15(21)9-14(20)11-2-4-17-18(8-11)25-10-24-17/h2-8H,9-10H2,1H3

> <INCHI_KEY>
SDJBCBKWKASUCJ-UHFFFAOYSA-N

> <FORMULA>
C19H14O6

> <MOLECULAR_WEIGHT>
338.3109

> <EXACT_MASS>
338.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.45354317111138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2H-1,3-benzodioxol-5-yl)-3-(4-methoxy-1-benzofuran-5-yl)propane-1,3-dione

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.802046432333332

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.112504000895807

> <JCHEM_PKA_STRONGEST_BASIC>
-3.035071278635205

> <JCHEM_POLAR_SURFACE_AREA>
74.97000000000001

> <JCHEM_REFRACTIVITY>
87.69319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ovalitenone

> <JCHEM_VEBER_RULE>
0

$$$$

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       3.864  12.853   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.137  10.543   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.531   8.233   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.471  11.313   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.865   9.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.852  12.819   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.383  12.980   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.471   8.233   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   9.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.174   9.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.137   9.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.198   9.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.531  11.313   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   8.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.865  10.543   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.804  10.543   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.804   9.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.198  10.543   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.197   6.693   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.864   6.693   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.864  11.313   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.010  11.573   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.269  11.019   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.269   8.527   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    4   11                                                       
CONECT    3    5   12                                                       
CONECT    4    2   17                                                       
CONECT    5    3   16                                                       
CONECT    6    7   13                                                       
CONECT    7    6   23                                                       
CONECT    8   11   18                                                       
CONECT    9   14   15                                                       
CONECT   10   24   25                                                       
CONECT   11    2    8   14                                                  
CONECT   12    3   15   19                                                  
CONECT   13    6   16   19                                                  
CONECT   14    9   11   20                                                  
CONECT   15    9   12   21                                                  
CONECT   16    5   13   23                                                  
CONECT   17    4   18   24                                                  
CONECT   18    8   17   25                                                  
CONECT   19   12   13   22                                                  
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22    1   19                                                       
CONECT   23    7   16                                                       
CONECT   24   10   17                                                       
CONECT   25   10   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
1-(1,3-Benzodioxol-5-yl)-3-(4-methoxy-5-benzofuranyl)-1,3-propanedione, 9ci	HMDB
Glabra I	HMDB

Chemical Formula

C₁₉H₁₄O₆

Average Mass

338.3109 Da

Monoisotopic Mass

338.07904 Da

IUPAC Name

1-(2H-1,3-benzodioxol-5-yl)-3-(4-methoxy-1-benzofuran-5-yl)propane-1,3-dione

Traditional Name

ovalitenone

CAS Registry Number

Not Available

SMILES

COC1=C(C=CC2=C1C=CO2)C(=O)CC(=O)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C19H14O6/c1-22-19-12(3-5-16-13(19)6-7-23-16)15(21)9-14(20)11-2-4-17-18(8-11)25-10-24-17/h2-8H,9-10H2,1H3

InChI Key

SDJBCBKWKASUCJ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dahlstedtia pinnata	Plant	KNApSAcK
Derris ovalifolia	LOTUS Database	35616633
Milletia ovalifolia	-	KNApSAcK
Millettia erythrocalyx	Plant	KNApSAcK
Millettia ovalifolia	Plant	KNApSAcK
Millettia peguensis	LOTUS Database	35616633
Pongamia pinnata	Plant	KNApSAcK
Rhus chinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retro-dihydrochalcones

Alternative Parents

Substituents

Retro-dihydrochalcone
Butyrophenone
Benzodioxole
Benzofuran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1,3-diketone
1,3-dicarbonyl compound
Benzenoid
Furan
Heteroaromatic compound
Ketone
Acetal
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120372 )

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	2.95	ALOGPS
logP	2.8	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.69 m³·mol⁻¹	ChemAxon
Polarizability	33.45 Å³	ChemAxon
Number of Rings	4	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

HMDB0030619

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002517

KNApSAcK ID

C00007017

Chemspider ID

545372

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

627910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ovalitenone (NP0054716)

MOL for NP0054716 (Ovalitenone)

3D MOL for NP0054716 (Ovalitenone)

3D SDF for NP0054716 (Ovalitenone)

3D-SDF for NP0054716 (Ovalitenone)

PDB for NP0054716 (Ovalitenone)

3D PDB for NP0054716 (Ovalitenone)

SMILES for NP0054716 (Ovalitenone)

INCHI for NP0054716 (Ovalitenone)

Structure for NP0054716 (Ovalitenone)

3D Structure for NP0054716 (Ovalitenone)