NP-MRD: Showing NP-Card for 3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal (NP0297041)

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Record Information

Version

2.0

Created at

2022-09-10 07:01:18 UTC

Updated at

2022-09-10 07:01:18 UTC

NP-MRD ID

NP0297041

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

Description

3-[3-(Hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal is found in Balanophora japonica and Strychnos axillaris. 3-[3-(Hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502472D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004201502472D          

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 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  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  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 29 28  1  4  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297041

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(C(CO)C2=CC(C=CC=O)=C1)C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O11/c1-33-18-10-14(5-6-17(18)35-26-23(32)22(31)21(30)20(12-29)36-26)24-16(11-28)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h3-10,16,20-24,26,28-32H,11-12H2,1-2H3

> <INCHI_KEY>
RPOPBMQXJDSYEK-UHFFFAOYSA-N

> <FORMULA>
C26H30O11

> <MOLECULAR_WEIGHT>
518.515

> <EXACT_MASS>
518.178811786

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.38583939849094

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
-0.2731975739999996

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.192114244803616

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199571601858159

> <JCHEM_PKA_STRONGEST_BASIC>
-2.715308237104672

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
129.5433

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-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      -5.710  -2.637   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.940  -3.970   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.710  -5.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.940  -6.638   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.710  -7.971   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -7.250  -5.304   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -8.020  -6.638   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -8.020  -3.970   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.560  -3.970   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -7.250  -2.637   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.020  -1.303   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.259  -4.383   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   37  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   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    5   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   28   34                                                       
CONECT   34   33   23   35                                                  
CONECT   35   34   21   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₁

Average Mass

518.5150 Da

Monoisotopic Mass

518.17881 Da

IUPAC Name

3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

Traditional Name

3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

CAS Registry Number

Not Available

SMILES

COC1=C2OC(C(CO)C2=CC(C=CC=O)=C1)C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C(OC)=C1

InChI Identifier

InChI=1S/C26H30O11/c1-33-18-10-14(5-6-17(18)35-26-23(32)22(31)21(30)20(12-29)36-26)24-16(11-28)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h3-10,16,20-24,26,28-32H,11-12H2,1-2H3

InChI Key

RPOPBMQXJDSYEK-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
Balanophora japonica	LOTUS Database	35616633
Strychnos axillaris	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
Lignan glycoside
Neolignan skeleton
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Cinnamaldehyde
Coumaran
Benzofuran
Anisole
Phenoxy compound
Styrene
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Alpha,beta-unsaturated aldehyde
Enal
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Hydrocarbon derivative
Aldehyde
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen 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	1.19	ALOGPS
logP	-0.27	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.54 m³·mol⁻¹	ChemAxon
Polarizability	53.39 Å³	ChemAxon
Number of Rings	4	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal (NP0297041)

MOL for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

3D MOL for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

3D SDF for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

3D-SDF for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

PDB for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

3D PDB for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

SMILES for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

INCHI for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

Structure for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)

3D Structure for NP0297041 (3-[3-(hydroxymethyl)-7-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal)