NP-MRD: Showing NP-Card for 4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one (NP0267969)

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Record Information

Version

2.0

Created at

2022-09-08 12:55:45 UTC

Updated at

2022-09-08 12:55:45 UTC

NP-MRD ID

NP0267969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one

Description

4-[(2Z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2H-chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. 4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one is found in Dalbergia retusa. Based on a literature review very few articles have been published on 4-[(2Z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2H-chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214552D          

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 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 23 34  1  0  0  0  0
 22 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 20 38  1  0  0  0  0
 38 39  1  0  0  0  0
 10 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C[C@H](COC2=C1)C1=C(O)C=C2O\C(C=C(C3=CC=C(O)C=C3)C2=C1)=C1\C=CC(=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O7/c1-36-23-9-5-19-11-20(17-38-29(19)13-23)26-14-27-25(18-3-6-21(33)7-4-18)15-31(39-32(27)16-28(26)35)24-10-8-22(34)12-30(24)37-2/h3-10,12-16,20,33,35H,11,17H2,1-2H3/b31-24-/t20-/m1/s1

> <INCHI_KEY>
KUPOABZYIVBMBM-MRHLFUAJSA-N

> <FORMULA>
C32H26O7

> <MOLECULAR_WEIGHT>
522.553

> <EXACT_MASS>
522.167853177

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
56.2340266886522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2Z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2H-chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one

> <JCHEM_LOGP>
4.649268823333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.41393733015633

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.738942235502899

> <JCHEM_PKA_STRONGEST_BASIC>
-4.318131051475016

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
160.503

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2Z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -7.700   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       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002   1.540   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       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      20.005  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   39                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   12   21   38                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33   23                                                       
CONECT   35   22   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   20   39                                                  
CONECT   39   38   10                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₆O₇

Average Mass

522.5530 Da

Monoisotopic Mass

522.16785 Da

IUPAC Name

4-[(2Z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2H-chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one

Traditional Name

4-[(2Z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3S)-7-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C[C@H](COC2=C1)C1=C(O)C=C2O\C(C=C(C3=CC=C(O)C=C3)C2=C1)=C1\C=CC(=O)C=C1OC

InChI Identifier

InChI=1S/C32H26O7/c1-36-23-9-5-19-11-20(17-38-29(19)13-23)26-14-27-25(18-3-6-21(33)7-4-18)15-31(39-32(27)16-28(26)35)24-10-8-22(34)12-30(24)37-2/h3-10,12-16,20,33,35H,11,17H2,1-2H3/b31-24-/t20-/m1/s1

InChI Key

KUPOABZYIVBMBM-MRHLFUAJSA-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
Dalbergia retusa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
7-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Isoflavanol
Neoflavonoid skeleton
Neoflavene
Isoflavan
1-benzopyran
Benzopyran
Chromane
Quinomethane
P-quinomethane
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.65	ChemAxon
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	160.5 m³·mol⁻¹	ChemAxon
Polarizability	56.23 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4481105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5323555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one (NP0267969)

MOL for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

3D MOL for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

3D SDF for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

3D-SDF for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

PDB for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

3D PDB for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

SMILES for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

INCHI for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

Structure for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)

3D Structure for NP0267969 (4-[(2z)-7-hydroxy-4-(4-hydroxyphenyl)-6-[(3s)-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]chromen-2-ylidene]-3-methoxycyclohexa-2,5-dien-1-one)