NP-MRD: Showing NP-Card for 5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin (NP0057174)

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Record Information

Version

2.0

Created at

2022-04-28 02:41:30 UTC

Updated at

2022-04-28 02:41:30 UTC

NP-MRD ID

NP0057174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin

Description

5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin, also known as coutareagenin, belongs to the class of organic compounds known as neoflavones. These are neoflavonoids with a structure based on the 4-phenylcoumarin skeleton. Thus, 5,3',4'-trihydroxy-7-methoxy-4-phenylcoumarin is considered to be a flavonoid. 5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin is found in Coutarea hexandra , Coutarea latiflora, Exostema caribaeum and Hintonia latiflora. Based on a literature review very few articles have been published on 5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    5.5813   -0.9795   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3388   -1.6608   -0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1614   -0.9291   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860   -1.6215    0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781   -0.9457    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4153   -1.6478    0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    0.4221   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3773    1.1373   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7124    0.5533    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328    0.8350    1.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174    0.3514    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3378   -0.4604    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6316   -0.9413    0.2803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5184   -0.7381   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0024   -1.5370   -1.9222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148   -0.2390   -0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2499    2.5273   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    3.1568   -0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0880    4.3938   -0.5089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    2.4292   -0.3427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9847    1.1144   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1572    0.4207   -0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3810   -1.6793    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6093   -0.5899   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5924   -0.1402    0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853   -2.7075    0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696   -2.6499    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382    1.4602    1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802    0.5583    2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0410   -1.5225   -0.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9043   -1.9545   -1.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6243   -0.5015   -1.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1442    3.1109   -0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952    0.9749   -0.2958 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
  5  7  2  0
  7 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 21 22  2  0
 22  3  1  0
  8  7  1  0
 16  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 17 33  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 22 34  1  0
M  END


  Mrv1652304282204412D          

 22 24  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    1.4289   -0.0000    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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    2.0625    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    2.0625    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
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  7  9  1  0  0  0  0
  3  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
  4 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 19  2  0  0  0  0
 18 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(OC(=O)C=C2C2=CC=C(O)C(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-9-5-13(19)16-10(7-15(20)22-14(16)6-9)8-2-3-11(17)12(18)4-8/h2-7,17-19H,1H3

> <INCHI_KEY>
DEVKCCHIUHLHCF-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.247189308265156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.148190962333333

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.098939786037397

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.394738896835588

> <JCHEM_PKA_STRONGEST_BASIC>
-4.842844823757811

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
87.50720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2   19   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3                                                       
CONECT   10    5   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18    4   19   20                                                  
CONECT   19   18    1                                                       
CONECT   20   18                                                            
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Coutareagenin	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2660 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

4-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-2H-chromen-2-one

Traditional Name

4-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(OC(=O)C=C2C2=CC=C(O)C(O)=C2)=C1

InChI Identifier

InChI=1S/C16H12O6/c1-21-9-5-13(19)16-10(7-15(20)22-14(16)6-9)8-2-3-11(17)12(18)4-8/h2-7,17-19H,1H3

InChI Key

DEVKCCHIUHLHCF-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
Coutarea hexandra	Plant	KNApSAcK
Coutarea latiflora	Plant	KNApSAcK
Exostema caribaeum	LOTUS Database	35616633
Hintonia latiflora	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
Hydroxycoumarin
Coumarin
Benzopyran
1-benzopyran
Anisole
Catechol
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Neoflavonoids (LMPK12100045 )

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	2.15	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.39	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.51 m³·mol⁻¹	ChemAxon
Polarizability	29.25 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

HMDB0250025

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00010208

Chemspider ID

8058448

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9882773

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin (NP0057174)

MOL for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

3D MOL for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

3D SDF for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

3D-SDF for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

PDB for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

3D PDB for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

SMILES for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

INCHI for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

Structure for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)

3D Structure for NP0057174 (5,3',4'-Trihydroxy-7-methoxy-4-phenylcoumarin)