NP-MRD: Showing NP-Card for 4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol (NP0191628)

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Record Information

Version

2.0

Created at

2022-09-04 08:39:32 UTC

Updated at

2022-09-04 08:39:33 UTC

NP-MRD ID

NP0191628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol

Description

4-[7-Hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. 4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol is found in Maackia tenuifolia. Based on a literature review very few articles have been published on 4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210392D          

 33 36  0  0  0  0            999 V2000
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    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042210392D          

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M  END
> <DATABASE_ID>
NP0191628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C2COC3=CC(O)=CC=C3C2C2=C(O)C=C(O)C(=C2)C(C)(C)C=C)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O6/c1-5-27(2,3)21-12-19(23(30)13-24(21)31)26-18-8-6-15(28)10-25(18)33-14-20(26)17-9-7-16(32-4)11-22(17)29/h5-13,20,26,28-31H,1,14H2,2-4H3

> <INCHI_KEY>
VHXUYQLQLXQKKP-UHFFFAOYSA-N

> <FORMULA>
C27H28O6

> <MOLECULAR_WEIGHT>
448.515

> <EXACT_MASS>
448.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
47.889318414452305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol

> <JCHEM_LOGP>
5.533335986666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.511967102306814

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.98469660378687

> <JCHEM_PKA_STRONGEST_BASIC>
-4.545182187191099

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
127.33979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   5.954   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770   3.286   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -2.310   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  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   20   28                                                  
CONECT   28   27                                                            
CONECT   29    8   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    6   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₆

Average Mass

448.5150 Da

Monoisotopic Mass

448.18859 Da

IUPAC Name

4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol

Traditional Name

4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C2COC3=CC(O)=CC=C3C2C2=C(O)C=C(O)C(=C2)C(C)(C)C=C)C(O)=C1

InChI Identifier

InChI=1S/C27H28O6/c1-5-27(2,3)21-12-19(23(30)13-24(21)31)26-18-8-6-15(28)10-25(18)33-14-20(26)17-9-7-16(32-4)11-22(17)29/h5-13,20,26,28-31H,1,14H2,2-4H3

InChI Key

VHXUYQLQLXQKKP-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
Maackia tenuifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

4p-methoxyisoflavonoid
Isoflavanol
Hydroxyisoflavonoid
Neoflavonoid skeleton
Neoflavan
Isoflavan
Stilbene
Methoxyphenol
1-benzopyran
Benzopyran
Chromane
Phenylpropane
Phenoxy compound
Methoxybenzene
Phenol ether
Resorcinol
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	5.53	ChemAxon
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.34 m³·mol⁻¹	ChemAxon
Polarizability	47.89 Å³	ChemAxon
Number of Rings	4	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

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

163106293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol (NP0191628)

MOL for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

3D MOL for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

3D SDF for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

3D-SDF for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

PDB for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

3D PDB for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

SMILES for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

INCHI for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

Structure for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)

3D Structure for NP0191628 (4-[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-yl]-6-(2-methylbut-3-en-2-yl)benzene-1,3-diol)