NP-MRD: Showing NP-Card for 3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid (NP0265475)

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Record Information

Version

2.0

Created at

2022-09-08 09:28:10 UTC

Updated at

2022-09-08 09:28:11 UTC

NP-MRD ID

NP0265475

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

Description

3-[2-(4-Hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid is found in Hibiscus cannabinus. 3-[2-(4-Hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161519412D          

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M  END

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M  END


  Mrv1533004161519412D          

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 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265475

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(C(CO)C2=CC(C=CC(=O)NCCC2=CC=C(O)C=C2)=C1)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H29NO7/c1-34-24-15-19(6-9-23(24)32)27-22(16-30)21-13-18(14-25(35-2)28(21)36-27)5-10-26(33)29-12-11-17-3-7-20(31)8-4-17/h3-10,13-15,22,27,30-32H,11-12,16H2,1-2H3,(H,29,33)

> <INCHI_KEY>
ICUAPJINGJGHPQ-UHFFFAOYSA-N

> <FORMULA>
C28H29NO7

> <MOLECULAR_WEIGHT>
491.54

> <EXACT_MASS>
491.194402278

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
54.1515871519976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
3.2797892243333338

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.05398388479971

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.360573012713736

> <JCHEM_PKA_STRONGEST_BASIC>
-0.38807461970679913

> <JCHEM_POLAR_SURFACE_AREA>
117.48000000000002

> <JCHEM_REFRACTIVITY>
136.3917

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -4.940   1.365   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.925  -6.693   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      10.259  -4.383   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      11.592  -5.153   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.926  -4.383   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.260  -5.153   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.593  -4.383   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.927  -5.153   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.927  -6.693   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.261  -7.463   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.593  -7.463   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.260  -6.693   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   34                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   17   33                                                       
CONECT   33   32   12   34                                                  
CONECT   34   33   10   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
3-[2-(4-Hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate	Generator

Chemical Formula

C₂₈H₂₉NO₇

Average Mass

491.5400 Da

Monoisotopic Mass

491.19440 Da

IUPAC Name

3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

Traditional Name

3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

CAS Registry Number

Not Available

SMILES

COC1=C2OC(C(CO)C2=CC(C=CC(=O)NCCC2=CC=C(O)C=C2)=C1)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C28H29NO7/c1-34-24-15-19(6-9-23(24)32)27-22(16-30)21-13-18(14-25(35-2)28(21)36-27)5-10-26(33)29-12-11-17-3-7-20(31)8-4-17/h3-10,13-15,22,27,30-32H,11-12,16H2,1-2H3,(H,29,33)

InChI Key

ICUAPJINGJGHPQ-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
Hibiscus cannabinus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Methoxyphenol
Coumaran
Benzofuran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Carboximidic acid
Carboximidic acid derivative
Ether
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Primary alcohol
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	3.23	ALOGPS
logP	3.28	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	117.48 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.39 m³·mol⁻¹	ChemAxon
Polarizability	54.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

75251062

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid (NP0265475)

MOL for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D MOL for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D SDF for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D-SDF for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

PDB for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D PDB for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

SMILES for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

INCHI for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

Structure for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D Structure for NP0265475 (3-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)