NP-MRD: Showing NP-Card for (2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one (NP0315985)

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Record Information

Version

2.0

Created at

2022-09-11 14:53:14 UTC

Updated at

2022-09-11 14:53:14 UTC

NP-MRD ID

NP0315985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Yuccaol A belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one is found in Yucca schidigera. (2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one was first documented in 2004 (PMID: 15240183). Based on a literature review very few articles have been published on Yuccaol A (PMID: 16580641).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112216532D          

 37 42  0  0  1  0            999 V2000
    2.0271    2.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974    2.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442   -0.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7390   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001   -0.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4399   -1.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6994   -1.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6441   -2.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964   -3.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816   -2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5221   -2.9095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2974    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125    1.6320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.4991    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -0.5697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3895    3.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  3  4  1  0  0  0  0
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 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
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    0.9987    1.8211   -4.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1196    1.3081   -4.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112216532D          

 37 42  0  0  1  0            999 V2000
    2.0271    2.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974    2.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0315985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C\C2=C3C(OC(=O)[C@@]33[C@H](OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C=C3)=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H20O8/c30-18-7-2-15(3-8-18)1-4-17-11-20(32)13-23-25(17)29(28(35)37-23)26-22(34)12-21(33)14-24(26)36-27(29)16-5-9-19(31)10-6-16/h1-14,27,30-34H/b4-1+/t27-,29+/m1/s1

> <INCHI_KEY>
YOJXOIWMUVWNAB-JKFOSBIYSA-N

> <FORMULA>
C29H20O8

> <MOLECULAR_WEIGHT>
496.471

> <EXACT_MASS>
496.115817604

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.659480245394676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
5.360794607666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.740063076918286

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.179308274383219

> <JCHEM_PKA_STRONGEST_BASIC>
-4.925349683523728

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
134.52299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       3.784   5.364   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.289   4.292   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.753   3.816   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.753   2.276   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.898   1.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.577  -0.260   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.923  -1.128   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.113  -0.736   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.968   0.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.800  -1.040   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.688  -2.715   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.306  -3.394   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.202  -4.931   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.180  -5.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.459  -4.752   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.841  -5.431   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.356  -3.216   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.026  -2.537   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.289   1.800   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.383   3.046   0.000  0.00  0.00           C+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  -1.063   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      -1.236  -1.120   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  O   UNK     0       4.382  10.151   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.936   7.542   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.460   6.077   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19    9    4   20                                                  
CONECT   20   19    2   21   30                                             
CONECT   21   20   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   20   31                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₀O₈

Average Mass

496.4710 Da

Monoisotopic Mass

496.11582 Da

IUPAC Name

(2'R,3S)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2H,2'H-3,3'-spirobi[[1]benzofuran]-2-one

Traditional Name

(2'R,3S)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2'H-3,3'-spirobi[[1]benzofuran]-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C\C2=C3C(OC(=O)[C@@]33[C@H](OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C=C3)=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C29H20O8/c30-18-7-2-15(3-8-18)1-4-17-11-20(32)13-23-25(17)29(28(35)37-23)26-22(34)12-21(33)14-24(26)36-27(29)16-5-9-19(31)10-6-16/h1-14,27,30-34H/b4-1+/t27-,29+/m1/s1

InChI Key

YOJXOIWMUVWNAB-JKFOSBIYSA-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
Coumaran
Benzofuran
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen 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
logP	5.36	ChemAxon
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	134.52 m³·mol⁻¹	ChemAxon
Polarizability	48.66 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

C00058079

Chemspider ID

8430746

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10255261

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Balestrieri C, Felice F, Piacente S, Pizza C, Montoro P, Oleszek W, Visciano V, Balestrieri ML: Relative effects of phenolic constituents from Yucca schidigera Roezl. bark on Kaposi's sarcoma cell proliferation, migration, and PAF synthesis. Biochem Pharmacol. 2006 May 14;71(10):1479-87. doi: 10.1016/j.bcp.2006.01.021. Epub 2006 Mar 6. [PubMed:16580641 ]
Marzocco S, Piacente S, Pizza C, Oleszek W, Stochmal A, Pinto A, Sorrentino R, Autore G: Inhibition of inducible nitric oxide synthase expression by yuccaol C from Yucca schidigera roezl. Life Sci. 2004 Aug 6;75(12):1491-501. doi: 10.1016/j.lfs.2004.03.013. [PubMed:15240183 ]
LOTUS database [Link]

Showing NP-Card for (2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one (NP0315985)

MOL for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D MOL for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D SDF for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D-SDF for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

PDB for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D PDB for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

SMILES for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

INCHI for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

Structure for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)

3D Structure for NP0315985 ((2'r,3s)-4',6,6'-trihydroxy-2'-(4-hydroxyphenyl)-4-[(1e)-2-(4-hydroxyphenyl)ethenyl]-2'h-3,3'-spirobi[[1]benzofuran]-2-one)