NP-MRD: Showing NP-Card for 4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one (NP0245612)

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Record Information

Version

2.0

Created at

2022-09-07 06:45:35 UTC

Updated at

2022-09-07 06:45:36 UTC

NP-MRD ID

NP0245612

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

Description

4,6,8',11'-Tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2H-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]Tridecane]-1'(9'),2'(6'),7'-trien-4'-one belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one is found in Abies sachalinensis and Yucca schidigera. 4,6,8',11'-Tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2H-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]Tridecane]-1'(9'),2'(6'),7'-trien-4'-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241501012D          

 40 46  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241501012D          

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 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 12 22  1  0  0  0  0
 15 22  1  0  0  0  0
 13 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
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 12 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  2  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  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
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 34 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245612

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(O)C=C3OC(=O)C4(C(OC5=CC(O)=CC(O)=C45)C4=CC=C(O)C=C4)C3=C2OC1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)26-21(36)11-18-19(34)12-23-25(27(18)40-26)30(29(37)39-23)24-20(35)9-17(33)10-22(24)38-28(30)14-3-7-16(32)8-4-14/h1-10,12,21,26,28,31-36H,11H2

> <INCHI_KEY>
RNDNBGULZNCSNB-UHFFFAOYSA-N

> <FORMULA>
C30H22O10

> <MOLECULAR_WEIGHT>
542.496

> <EXACT_MASS>
542.121296908

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.91829958785834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2H-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
4.057076058333333

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.045384890022104

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.588601347676589

> <JCHEM_PKA_STRONGEST_BASIC>
-3.293601310697049

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
139.08629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2H-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       0.290   1.978   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.884   2.367   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.822   3.906   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.124   4.729   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.062   6.268   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.813   7.294   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.364   7.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727   6.374   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.172   6.909   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.126   5.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.405   5.682   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.271   4.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.754   4.002   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.816   2.463   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.371   1.929   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.802   0.498   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.278   0.276   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.590  -1.552   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.323   1.485   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.893   2.916   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.308   3.619   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.417   3.138   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.963   4.956   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.740   6.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.949   7.435   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.380   6.865   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.589   7.819   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.602   5.341   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.393   4.387   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.789   4.836   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.487   4.013   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.549   2.474   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.247   1.651   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.309   0.113   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.672  -0.603   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.734  -2.142   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.432  -2.965   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.494  -4.504   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.069  -2.249   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.007  -0.710   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   22   30                                             
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   12   15                                                  
CONECT   23   13   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
CONECT   30   12    8   31                                                  
CONECT   31   30    4   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32    2   34                                                  
CONECT   34   33   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   34                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Value	Source
3,2'-Epi-larixinol	MeSH
3-Epi-larixinol	MeSH

Chemical Formula

C₃₀H₂₂O₁₀

Average Mass

542.4960 Da

Monoisotopic Mass

542.12130 Da

IUPAC Name

4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2H-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

Traditional Name

4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2H-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one

CAS Registry Number

Not Available

SMILES

OC1CC2=C(O)C=C3OC(=O)C4(C(OC5=CC(O)=CC(O)=C45)C4=CC=C(O)C=C4)C3=C2OC1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)26-21(36)11-18-19(34)12-23-25(27(18)40-26)30(29(37)39-23)24-20(35)9-17(33)10-22(24)38-28(30)14-3-7-16(32)8-4-14/h1-10,12,21,26,28,31-36H,11H2

InChI Key

RNDNBGULZNCSNB-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
Abies sachalinensis	LOTUS Database	35616633
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
Lignan lactone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Neolignan skeleton
Flavan
Chromane
Benzopyran
1-benzopyran
Benzofuran
Coumaran
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic oxide
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	3.59	ALOGPS
logP	4.06	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.59	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	139.09 m³·mol⁻¹	ChemAxon
Polarizability	51.92 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

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

73822597

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one (NP0245612)

MOL for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

3D MOL for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

3D SDF for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

3D-SDF for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

PDB for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

3D PDB for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

SMILES for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

INCHI for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

Structure for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)

3D Structure for NP0245612 (4,6,8',11'-tetrahydroxy-2,12'-bis(4-hydroxyphenyl)-2h-5',13'-dioxaspiro[1-benzofuran-3,3'-tricyclo[7.4.0.0²,⁶]tridecane]-1',6',8'-trien-4'-one)