NP-MRD: Showing NP-Card for rengasin trimethyl ether (NP0279433)

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Record Information

Version

2.0

Created at

2022-09-09 04:49:24 UTC

Updated at

2022-09-09 04:49:24 UTC

NP-MRD ID

NP0279433

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rengasin trimethyl ether

Description

2-[(3,4-Dimethoxyphenyl)methylidene]-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-one belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). Thus, 2-[(3,4-dimethoxyphenyl)methylidene]-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-one is considered to be a flavonoid lipid molecule. rengasin trimethyl ether is found in Cyperus capitatus. 2-[(3,4-Dimethoxyphenyl)methylidene]-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -6.6640    2.0083   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1517    0.7621   -0.6378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7840    0.5226   -0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2569   -0.6829   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9195   -0.9630   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269   -2.1327   -1.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758   -3.2235   -1.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225    0.0114   -0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    1.2166    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9485    1.4709    0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5989    2.0023    0.8030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3734    1.3037    0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7880    1.7538    1.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482    1.0416    1.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570    0.8398    2.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0698    0.1902    2.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5352   -0.2944    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7563   -0.9577    0.7918 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5349   -1.1267    1.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -0.1032   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2173   -0.5943   -1.4068 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4309   -0.4157   -2.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5089    0.5613   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705    0.0303    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115   -0.9174   -0.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3702    2.1724    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7810    1.9926   -0.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2848    2.7978   -0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8633   -1.4694   -1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -4.1320   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9860   -3.3696   -1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0589   -2.9805   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905    2.4192    0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    2.7737    1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5472    1.1968    3.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7037    0.0337    2.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8184   -0.1004    2.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9261   -1.5784    2.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4799   -1.6463    1.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755   -0.7037   -2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161   -1.0742   -3.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291    0.6654   -2.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9477    0.6995   -1.0289 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
  6  7  1  0
  5  8  2  0
  8 24  1  0
 24 25  2  0
 24 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 10  3  1  0
 23 14  1  0
  9  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
 10 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END


  Mrv1533004171500342D          

 25 27  0  0  0  0            999 V2000
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    4.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    4.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 13 22  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0279433

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(=O)C(OC2=C1)=CC1=CC=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O6/c1-21-12-9-15(24-4)18-16(10-12)25-17(19(18)20)8-11-5-6-13(22-2)14(7-11)23-3/h5-10H,1-4H3

> <INCHI_KEY>
CVKDSGICIOMAGA-UHFFFAOYSA-N

> <FORMULA>
C19H18O6

> <MOLECULAR_WEIGHT>
342.347

> <EXACT_MASS>
342.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.231899964372445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3,4-dimethoxyphenyl)methylidene]-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
2.5715892536666667

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2594605993366565

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
92.8991

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rengasin trimethyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.400   5.510   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.630   6.844   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.400   8.178   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.940   8.178   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.090   6.844   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.320   8.178   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.220   8.178   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.320   5.510   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   24                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   13                                                       
CONECT   23   11   24                                                       
CONECT   24   23    8   25                                                  
CONECT   25   24    3                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₈O₆

Average Mass

342.3470 Da

Monoisotopic Mass

342.11034 Da

IUPAC Name

2-[(3,4-dimethoxyphenyl)methylidene]-4,6-dimethoxy-2,3-dihydro-1-benzofuran-3-one

Traditional Name

rengasin trimethyl ether

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(=O)C(OC2=C1)=CC1=CC=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C19H18O6/c1-21-12-9-15(24-4)18-16(10-12)25-17(19(18)20)8-11-5-6-13(22-2)14(7-11)23-3/h5-10H,1-4H3

InChI Key

CVKDSGICIOMAGA-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

Species Name	Source	Reference
Cyperus capitatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Dimethoxybenzene
O-dimethoxybenzene
Benzofuran
Coumaran
Anisole
Phenoxy compound
Phenol ether
Aryl ketone
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Aurone flavonoids (LMPK12130052 )

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	3.48	ALOGPS
logP	2.57	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	92.9 m³·mol⁻¹	ChemAxon
Polarizability	36.23 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for rengasin trimethyl ether (NP0279433)

MOL for NP0279433 (rengasin trimethyl ether)

3D MOL for NP0279433 (rengasin trimethyl ether)

3D SDF for NP0279433 (rengasin trimethyl ether)

3D-SDF for NP0279433 (rengasin trimethyl ether)

PDB for NP0279433 (rengasin trimethyl ether)

3D PDB for NP0279433 (rengasin trimethyl ether)

SMILES for NP0279433 (rengasin trimethyl ether)

INCHI for NP0279433 (rengasin trimethyl ether)

Structure for NP0279433 (rengasin trimethyl ether)

3D Structure for NP0279433 (rengasin trimethyl ether)