NP-MRD: Showing NP-Card for (3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one (NP0239949)

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Record Information

Version

2.0

Created at

2022-09-06 23:38:42 UTC

Updated at

2022-09-06 23:38:42 UTC

NP-MRD ID

NP0239949

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one

Description

NSC720591 belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one is found in Yucca schidigera. Based on a literature review very few articles have been published on NSC720591.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201382D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072201382D          

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 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 31 37  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  2  0  0  0  0
  3 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(\C=C\C2=CC(O)=CC3=C2[C@@]2(C(OC4=CC(O)=CC(O)=C24)C2=CC=CC(O)=C2)C(=O)O3)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O10/c1-38-27-21(35)7-14(8-22(27)36)5-6-15-9-18(32)12-23-25(15)30(29(37)40-23)26-20(34)11-19(33)13-24(26)39-28(30)16-3-2-4-17(31)10-16/h2-13,28,31-36H,1H3/b6-5+/t28?,30-/m1/s1

> <INCHI_KEY>
KHGBPZCKVUBCGO-FMWPOBPCSA-N

> <FORMULA>
C30H22O10

> <MOLECULAR_WEIGHT>
542.496

> <EXACT_MASS>
542.121296908

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.74901539152772

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-4-[(E)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2H,2'H-3,3'-spirobi[[1]benzofuran]-2-one

> <JCHEM_LOGP>
4.899558020333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.767802200394646

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.193054343506759

> <JCHEM_PKA_STRONGEST_BASIC>
-4.638933409043246

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
142.9671

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-4-[(E)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'H-3,3'-spirobi[[1]benzofuran]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.688  -7.168   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.655  -5.629   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.306  -4.887   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.273  -3.347   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.590  -2.549   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.077  -2.606   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.394  -3.403   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.743  -2.662   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.779  -0.963   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.968   0.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.113  -0.736   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.577  -0.260   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.929  -1.197   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.898   1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.753   2.276   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.289   1.800   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.383   3.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.289   4.292   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.807   5.452   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.753   3.816   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.478   1.800   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.798   0.294   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.993  -1.054   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.654  -0.736   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.189  -0.260   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.124  -1.190   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.131   1.246   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.013   2.276   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.013   3.816   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.478   4.292   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.954   5.757   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.924   6.901   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.399   8.366   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.906   8.686   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.936   7.542   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.443   7.862   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.460   6.077   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.361  -4.943   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.012  -5.685   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.021  -7.224   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   38                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18   21   30                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   15                                                       
CONECT   21   17   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   17   31                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   31                                                       
CONECT   38    7   39                                                       
CONECT   39   38    3   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₀

Average Mass

542.4960 Da

Monoisotopic Mass

542.12130 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(\C=C\C2=CC(O)=CC3=C2[C@@]2(C(OC4=CC(O)=CC(O)=C24)C2=CC=CC(O)=C2)C(=O)O3)C=C1O

InChI Identifier

InChI=1S/C30H22O10/c1-38-27-21(35)7-14(8-22(27)36)5-6-15-9-18(32)12-23-25(15)30(29(37)40-23)26-20(34)11-19(33)13-24(26)39-28(30)16-3-2-4-17(31)10-16/h2-13,28,31-36H,1H3/b6-5+/t28?,30-/m1/s1

InChI Key

KHGBPZCKVUBCGO-FMWPOBPCSA-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
Yucca schidigera	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
Stilbene
Methoxyphenol
Benzofuran
Coumaran
Phenol ether
Resorcinol
Phenoxy compound
Styrene
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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

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

4582533

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5472642

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one (NP0239949)

MOL for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D MOL for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D SDF for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D-SDF for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

PDB for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D PDB for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

SMILES for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

INCHI for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

Structure for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D Structure for NP0239949 ((3r)-4-[(1e)-2-(3,5-dihydroxy-4-methoxyphenyl)ethenyl]-4',6,6'-trihydroxy-2'-(3-hydroxyphenyl)-2'h-3,3'-spirobi[[1]benzofuran]-2-one)