NP-MRD: Showing NP-Card for 6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone (NP0062949)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 07:28:03 UTC

Updated at

2022-04-28 07:28:03 UTC

NP-MRD ID

NP0062949

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone

Description

3',6,8-Trichloro-4',5-dihydroxy-7-methoxyisoflavone belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. 6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone is found in Ouratea semiserrata. Based on a literature review very few articles have been published on 3',6,8-Trichloro-4',5-dihydroxy-7-methoxyisoflavone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    6.0756   -0.3348   -0.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1603   -0.9681    0.3558 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7735   -0.8790    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0850   -1.7765   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9858   -3.0625   -1.3562 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -1.6685   -0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248   -2.6152   -1.5243 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530   -0.6446   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094   -0.4864   -0.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9904   -1.2732   -0.9193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620    0.5638    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023    0.7070    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2327   -0.3933    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5959   -0.3207    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1931    0.8947    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5740    1.0157   -0.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3579    1.9940   -0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1260    3.5333   -0.4391 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    1.9299    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    1.4306    1.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010    1.2795    1.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7206    0.2752    0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0831    0.1373    0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9225    1.3112    1.7873 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9088    0.1531    0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5398    0.4366   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5592   -1.0665   -1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -2.8256   -1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7720   -1.3486    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1872   -1.2283    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1295    0.1761   -0.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3459    2.7922   -0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530    2.2616    1.6880 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
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 23  3  1  0
 19 12  1  0
 22  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
 20 33  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 19 32  1  0
M  END


  Mrv1652304282209282D          

 24 26  0  0  0  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 Cl  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
    2.1434   -1.2375    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
    1.4289   -2.4750    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 Cl  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
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  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  2  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
  3 21  1  0  0  0  0
  2 22  1  0  0  0  0
  1 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Cl)C(O)=C2C(=O)C(=COC2=C1Cl)C1=CC=C(O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H9Cl3O5/c1-23-16-11(18)14(22)10-13(21)7(5-24-15(10)12(16)19)6-2-3-9(20)8(17)4-6/h2-5,20,22H,1H3

> <INCHI_KEY>
REXBVZLBTQFFQZ-UHFFFAOYSA-N

> <FORMULA>
C16H9Cl3O5

> <MOLECULAR_WEIGHT>
387.59

> <EXACT_MASS>
385.9515565

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
35.35000197617433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-dichloro-3-(3-chloro-4-hydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
4.90

> <JCHEM_LOGP>
5.034900474666667

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.44826256477385

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.650293783578453

> <JCHEM_PKA_STRONGEST_BASIC>
-4.826495047186946

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
90.5796

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dichloro-3-(3-chloro-4-hydroxyphenyl)-5-hydroxy-7-methoxychromen-4-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  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       0.000   1.540   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       6.668  -6.930   0.000  0.00  0.00          Cl+0
HETATM   20  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   22 Cl   UNK     0      -2.667  -3.080   0.000  0.00  0.00          Cl+0
HETATM   23  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6   23                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17                                                            
CONECT   20   16                                                            
CONECT   21    3                                                            
CONECT   22    2                                                            
CONECT   23    1   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₉Cl₃O₅

Average Mass

387.5900 Da

Monoisotopic Mass

385.95156 Da

IUPAC Name

6,8-dichloro-3-(3-chloro-4-hydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

Traditional Name

6,8-dichloro-3-(3-chloro-4-hydroxyphenyl)-5-hydroxy-7-methoxychromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(Cl)C(O)=C2C(=O)C(=COC2=C1Cl)C1=CC=C(O)C(Cl)=C1

InChI Identifier

InChI=1S/C16H9Cl3O5/c1-23-16-11(18)14(22)10-13(21)7(5-24-15(10)12(16)19)6-2-3-9(20)8(17)4-6/h2-5,20,22H,1H3

InChI Key

REXBVZLBTQFFQZ-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
Ouratea semiserrata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylisoflavones

Alternative Parents

Substituents

7-o-methylisoflavone
Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
2-halophenol
Anisole
2-chlorophenol
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Alkyl aryl ether
Chlorobenzene
Phenol
Pyranone
Aryl halide
Monocyclic benzene moiety
Aryl chloride
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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
logP	4.9	ALOGPS
logP	5.03	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.65	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.58 m³·mol⁻¹	ChemAxon
Polarizability	35.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00019705

Chemspider ID

28944416

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100927216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone (NP0062949)

MOL for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

3D MOL for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

3D SDF for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

3D-SDF for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

PDB for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

3D PDB for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

SMILES for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

INCHI for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

Structure for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)

3D Structure for NP0062949 (6,8,3'-Trichloro-5,4'-dihydroxy-7-methoxyisoflavone)