NP-MRD: Showing NP-Card for 5,7,4'-Trimethoxy-4-phenylcoumarin (NP0057168)

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Record Information

Version

2.0

Created at

2022-04-28 02:41:20 UTC

Updated at

2022-04-28 02:41:20 UTC

NP-MRD ID

NP0057168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,4'-Trimethoxy-4-phenylcoumarin

Description

5,7-Dimethoxy-4-(4-methoxyphenyl)-2H-chromen-2-one belongs to the class of organic compounds known as neoflavones. These are neoflavonoids with a structure based on the 4-phenylcoumarin skeleton. Thus, 5,7-dimethoxy-4-(4-methoxyphenyl)-2H-chromen-2-one is considered to be a flavonoid lipid molecule. 5,7,4'-Trimethoxy-4-phenylcoumarin is found in Chiococca alba, Coutarea hexandra , Exostema acuminatum, Exostema caribaeum and Kitasatospora aureofaciens. 5,7-Dimethoxy-4-(4-methoxyphenyl)-2H-chromen-2-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -6.0354    0.7283    1.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0097   -0.2013    1.2480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8040   -0.2002    0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4313    0.7364   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2018    0.6672   -0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2796   -0.3462   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146   -0.3981   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -0.7106   -2.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1357   -0.8217   -3.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1180   -1.1043   -4.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594   -0.6387   -2.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361   -0.3460   -1.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5550   -0.1582   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6657    0.1583    0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9032    0.3372    0.9517 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0907    0.2074    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423    0.2968    1.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962    0.1093    0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1616    0.2464    1.2910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939    0.5622    2.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935   -0.2093   -0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730   -1.2728    0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9103   -1.2071    0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0245    1.1158    0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0391    1.5285    1.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0069    0.1661    1.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329    1.5253   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021    1.4093   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110   -0.8504   -3.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -0.2625   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1235    0.9848   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1385   -0.7903   -0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9587    0.2630    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5395    0.5426    2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9435    0.3586    2.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7809   -0.0348    3.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2687    1.6549    2.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879   -2.0808    0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -1.9648    1.6155 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  2  0
  6 22  1  0
 22 23  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 23  3  1  0
 21  7  1  0
 21 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 22 38  1  0
 23 39  1  0
  8 29  1  0
 13 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
M  END

  Mrv1533004241508022D          

 23 25  0  0  0  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
  9 23  1  0  0  0  0
 14 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)OC2=CC(OC)=CC(OC)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-20-12-6-4-11(5-7-12)14-10-17(19)23-16-9-13(21-2)8-15(22-3)18(14)16/h4-10H,1-3H3

> <INCHI_KEY>
LUAQJOITTQBGCV-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.321

> <EXACT_MASS>
312.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.05140172347704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dimethoxy-4-(4-methoxyphenyl)-2H-chromen-2-one

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
2.7435443960000008

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.369431947235923

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
94.4909

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dimethoxy-4-(4-methoxyphenyl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20    9   14                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3210 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

5,7-dimethoxy-4-(4-methoxyphenyl)-2H-chromen-2-one

Traditional Name

5,7-dimethoxy-4-(4-methoxyphenyl)chromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC(=O)OC2=CC(OC)=CC(OC)=C12

InChI Identifier

InChI=1S/C18H16O5/c1-20-12-6-4-11(5-7-12)14-10-17(19)23-16-9-13(21-2)8-15(22-3)18(14)16/h4-10H,1-3H3

InChI Key

LUAQJOITTQBGCV-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
Chiococca alba	LOTUS Database	35616633
Coutarea hexandra	Plant	KNApSAcK
Exostema acuminatum	LOTUS Database	35616633
Exostema caribaeum	Plant	KNApSAcK
Kitasatospora aureofaciens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as neoflavones. These are neoflavonoids with a structure based on the 4-phenylcoumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Neoflavones

Direct Parent

Neoflavones

Alternative Parents

Substituents

4-phenylcoumarin
Coumarin
Benzopyran
1-benzopyran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Neoflavonoids (LMPK12100048 )

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	3.56	ALOGPS
logP	2.74	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.49 m³·mol⁻¹	ChemAxon
Polarizability	32.05 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7,4'-Trimethoxy-4-phenylcoumarin (NP0057168)

MOL for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

3D MOL for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

3D SDF for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

3D-SDF for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

PDB for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

3D PDB for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

SMILES for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

INCHI for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

Structure for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)

3D Structure for NP0057168 (5,7,4'-Trimethoxy-4-phenylcoumarin)