NP-MRD: Showing NP-Card for 2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one (NP0199875)

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Record Information

Version

2.0

Created at

2022-09-04 18:36:10 UTC

Updated at

2022-09-04 18:36:10 UTC

NP-MRD ID

NP0199875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one

Description

CHEMBL453028 belongs to the class of organic compounds known as phenylbenzofurans. These are organic aromatic compounds that contain a phenyl group attached to a benzofuran moiety. Benzofuran is a bicyclic compound containing a benzene fused to a furan. 2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one is found in Dalbergia cochinchinensis. Based on a literature review very few articles have been published on CHEMBL453028.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042220362D          

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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  1  0  0  0  0
 14 15  1  0  0  0  0
 13 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
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
  7 27  2  0  0  0  0
 27 28  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(OC(CC3=CC(C\C=C\C4=CC=CC=C4)(OC)C(OC)=CC3=O)=C2C2=CC=CC=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H30O6/c1-36-29-20-28-25(18-27(29)35)32(23-14-8-5-9-15-23)30(39-28)17-24-21-33(38-3,31(37-2)19-26(24)34)16-10-13-22-11-6-4-7-12-22/h4-15,18-21,35H,16-17H2,1-3H3/b13-10+

> <INCHI_KEY>
TZBPQIOKLWLNNI-JLHYYAGUSA-N

> <FORMULA>
C33H30O6

> <MOLECULAR_WEIGHT>
522.597

> <EXACT_MASS>
522.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.42624615729568

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2E)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one

> <JCHEM_LOGP>
6.123992306333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.148047124016653

> <JCHEM_PKA_STRONGEST_BASIC>
-2.822919118344878

> <JCHEM_POLAR_SURFACE_AREA>
78.13000000000001

> <JCHEM_REFRACTIVITY>
154.27199999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2E)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one

> <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      -2.630   5.366   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.400   4.032   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.630   2.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.090   2.698   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.320   1.365   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.220   1.365   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.400   1.365   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.759   0.642   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.065   1.458   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.425   0.735   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.731   1.551   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.091   0.828   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -11.397   1.644   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -11.343   3.183   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.983   3.906   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.677   3.090   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.759   2.088   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.813   3.627   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   11   20                                                  
CONECT   20   19    9   21                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27    7   28                                                       
CONECT   28   27    3   29   38                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   28   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₀O₆

Average Mass

522.5970 Da

Monoisotopic Mass

522.20424 Da

IUPAC Name

2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2E)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one

Traditional Name

2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2E)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(OC(CC3=CC(C\C=C\C4=CC=CC=C4)(OC)C(OC)=CC3=O)=C2C2=CC=CC=C2)=C1

InChI Identifier

InChI=1S/C33H30O6/c1-36-29-20-28-25(18-27(29)35)32(23-14-8-5-9-15-23)30(39-28)17-24-21-33(38-3,31(37-2)19-26(24)34)16-10-13-22-11-6-4-7-12-22/h4-15,18-21,35H,16-17H2,1-3H3/b13-10+

InChI Key

TZBPQIOKLWLNNI-JLHYYAGUSA-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 cochinchinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzofurans. These are organic aromatic compounds that contain a phenyl group attached to a benzofuran moiety. Benzofuran is a bicyclic compound containing a benzene fused to a furan.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Phenylbenzofurans

Direct Parent

Phenylbenzofurans

Alternative Parents

Substituents

Phenylbenzofuran
Anisole
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Vinylogous ester
Ketone
Cyclic ketone
Ether
Dialkyl ether
Oxacycle
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	6.12	ChemAxon
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	154.27 m³·mol⁻¹	ChemAxon
Polarizability	56.43 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8228018

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10052458

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one (NP0199875)

MOL for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

3D MOL for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

3D SDF for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

3D-SDF for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

PDB for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

3D PDB for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

SMILES for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

INCHI for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

Structure for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)

3D Structure for NP0199875 (2-[(5-hydroxy-6-methoxy-3-phenyl-1-benzofuran-2-yl)methyl]-4,5-dimethoxy-4-[(2e)-3-phenylprop-2-en-1-yl]cyclohexa-2,5-dien-1-one)