NP-MRD: Showing NP-Card for 2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol (NP0234978)

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Record Information

Version

2.0

Created at

2022-09-06 17:20:56 UTC

Updated at

2022-09-06 17:20:56 UTC

NP-MRD ID

NP0234978

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol

Description

SCHEMBL667754 belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol is found in Daphne feddei and Daphne odora. SCHEMBL667754 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507312D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251507312D          

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 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 25 37  1  0  0  0  0
 15 37  1  0  0  0  0
 37 38  2  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  0  0  0  0
  8 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1CCC2=C(O)C=C3OC(=C(C(=O)C4=C(O)C=C(O)C=C4O)C3=C2O1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)23-10-9-19-20(34)13-24-26(30(19)38-23)27(29(39-24)15-3-7-17(32)8-4-15)28(37)25-21(35)11-18(33)12-22(25)36/h1-8,11-13,23,31-36H,9-10H2

> <INCHI_KEY>
SFIBBWQCUADULX-UHFFFAOYSA-N

> <FORMULA>
C30H22O9

> <MOLECULAR_WEIGHT>
526.497

> <EXACT_MASS>
526.126382288

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
52.86733549951215

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
6.748582902666666

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.970842372167462

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.888406952812443

> <JCHEM_PKA_STRONGEST_BASIC>
-2.913729575596392

> <JCHEM_POLAR_SURFACE_AREA>
160.82

> <JCHEM_REFRACTIVITY>
141.03029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0      -1.530  -8.049   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.578  -6.776   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.306  -5.419   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.494  -4.110   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.045  -4.158   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.773  -5.515   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.962  -6.824   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.856  -2.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.128  -1.492   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.939  -0.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.479  -0.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.290   1.078   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.782   2.583   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.829   1.030   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.557  -0.327   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.053  -0.694   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.166  -2.230   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.634  -2.892   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.832  -2.313   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.141  -3.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.093  -4.664   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.632  -5.167   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.736  -5.392   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.427  -4.581   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.740  -2.812   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.325  -4.355   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.282  -5.509   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.485  -5.374   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.963  -4.944   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.544  -3.368   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.075  -6.009   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.708  -7.505   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.820  -8.571   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.229  -7.935   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.118  -6.869   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.847  -7.835   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.746  -1.636   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.207  -1.588   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.395  -2.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   39                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   38                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   17   26   37                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   35                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   28   36                                                  
CONECT   36   35                                                            
CONECT   37   25   15   38                                                  
CONECT   38   37   11   39                                                  
CONECT   39   38    8                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₉

Average Mass

526.4970 Da

Monoisotopic Mass

526.12638 Da

IUPAC Name

2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol

Traditional Name

2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1CCC2=C(O)C=C3OC(=C(C(=O)C4=C(O)C=C(O)C=C4O)C3=C2O1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)23-10-9-19-20(34)13-24-26(30(19)38-23)27(29(39-24)15-3-7-17(32)8-4-15)28(37)25-21(35)11-18(33)12-22(25)36/h1-8,11-13,23,31-36H,9-10H2

InChI Key

SFIBBWQCUADULX-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
Daphne feddei	LOTUS Database	35616633
Daphne odora	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
Furanoflavonoid or dihydroflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Flavan
2-phenylbenzofuran
Phenylbenzofuran
Aryl-phenylketone
Benzopyran
Chromane
1-benzopyran
Benzofuran
Benzenetriol
Phloroglucinol derivative
Aryl ketone
3-aroylfuran
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Furan
Vinylogous acid
Heteroaromatic compound
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxide
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	4.38	ALOGPS
logP	6.75	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.89	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	160.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.03 m³·mol⁻¹	ChemAxon
Polarizability	52.87 Å³	ChemAxon
Number of Rings	6	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

13915094

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol (NP0234978)

MOL for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

3D MOL for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

3D SDF for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

3D-SDF for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

PDB for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

3D PDB for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

SMILES for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

INCHI for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

Structure for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)

3D Structure for NP0234978 (2-[8-hydroxy-4,12-bis(4-hydroxyphenyl)-5,13-dioxatricyclo[7.4.0.0²,⁶]trideca-1,3,6,8-tetraene-3-carbonyl]benzene-1,3,5-triol)