NP-MRD: Showing NP-Card for 8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one (NP0296516)

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Record Information

Version

2.0

Created at

2022-09-10 06:08:28 UTC

Updated at

2022-09-10 06:08:29 UTC

NP-MRD ID

NP0296516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

7-O-methyl-8-chlorogenistein 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. Based on a literature review very few articles have been published on 7-O-methyl-8-chlorogenistein.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    6.1565    0.1318   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1191    0.7046    0.5541 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928    0.4264    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4337   -0.4424   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918   -0.7095   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -1.5749   -1.8788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1201   -0.0918   -0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -0.3368   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6087   -1.1219   -1.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    0.2881    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6112    0.0614    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    1.1677    0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    0.9505    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2864   -0.3109    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6597   -0.5777   -0.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4537   -1.4063    0.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022   -1.1979    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355    1.1506    1.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    1.3711    1.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650    0.7855    0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8121    1.0235    1.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151    2.1379    2.3611 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9709   -0.9494   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2683    0.6975   -1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1348    0.2406    0.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1555   -0.9460   -1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -2.0257   -2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0721    2.1739    0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5064    1.7725    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0180   -0.5829   -1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8594   -2.4085   -0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4239   -2.0417    0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688    1.6407    2.1129 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  8  1  0
  8  9  2  0
  8 10  1  0
 10 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 21  3  1  0
 17 11  1  0
 20  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 18 33  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END


  Mrv1652309102208082D          

 22 24  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    1.4289    0.8250    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
    2.8579    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   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 O   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 Cl  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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 10 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296516

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H11ClO5/c1-21-12-6-11(19)13-15(20)10(7-22-16(13)14(12)17)8-2-4-9(18)5-3-8/h2-7,18-19H,1H3

> <INCHI_KEY>
FLTULSFWLIRRSK-UHFFFAOYSA-N

> <FORMULA>
C16H11ClO5

> <MOLECULAR_WEIGHT>
318.71

> <EXACT_MASS>
318.0295012

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
30.897124543873662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.8268111219999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.968700900554982

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.008501669986984

> <JCHEM_PKA_STRONGEST_BASIC>
-4.788386915587917

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
80.97

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+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  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       2.667  -4.620   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11                                                       
CONECT   18   10   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    7   21                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₁ClO₅

Average Mass

318.7100 Da

Monoisotopic Mass

318.02950 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H11ClO5/c1-21-12-6-11(19)13-15(20)10(7-22-16(13)14(12)17)8-2-4-9(18)5-3-8/h2-7,18-19H,1H3

InChI Key

FLTULSFWLIRRSK-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

Not Available

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
Anisole
4-halophenol
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Pyran
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organohalogen compound
Organochloride
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	3.83	ChemAxon
pKa (Strongest Acidic)	7.01	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	80.97 m³·mol⁻¹	ChemAxon
Polarizability	30.9 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

34559155

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71583009

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one (NP0296516)

MOL for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

3D MOL for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

3D SDF for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

3D-SDF for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

PDB for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

3D PDB for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

SMILES for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

INCHI for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

Structure for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)

3D Structure for NP0296516 (8-chloro-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one)