NP-MRD: Showing NP-Card for [Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone (NP0060852)

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Record Information

Version

2.0

Created at

2022-04-28 05:50:02 UTC

Updated at

2022-04-28 05:50:02 UTC

NP-MRD ID

NP0060852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone

Description

4-[(2S,3R,4R,5S)-4-(2,4-dihydroxybenzoyl)-2,5-bis(4-hydroxyphenyl)oxolane-3-carbonyl]benzene-1,3-diol belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group). [Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone is found in Cordia goetzei. Based on a literature review very few articles have been published on 4-[(2S,3R,4R,5S)-4-(2,4-dihydroxybenzoyl)-2,5-bis(4-hydroxyphenyl)oxolane-3-carbonyl]benzene-1,3-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207502D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282207502D          

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 18 21  1  0  0  0  0
 16 22  1  0  0  0  0
  2 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 28 32  1  0  0  0  0
  1 33  1  1  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 36 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@H]1O[C@@H]([C@@H]([C@H]1C(=O)C1=CC=C(O)C=C1O)C(=O)C1=C(O)C=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O9/c31-17-5-1-15(2-6-17)29-25(27(37)21-11-9-19(33)13-23(21)35)26(28(38)22-12-10-20(34)14-24(22)36)30(39-29)16-3-7-18(32)8-4-16/h1-14,25-26,29-36H/t25-,26-,29+,30+/m0/s1

> <INCHI_KEY>
MGYYQYIFNBTUAB-SRPPIYJJSA-N

> <FORMULA>
C30H24O9

> <MOLECULAR_WEIGHT>
528.513

> <EXACT_MASS>
528.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
52.9148595330483

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2S,3R,4R,5S)-4-(2,4-dihydroxybenzoyl)-2,5-bis(4-hydroxyphenyl)oxolane-3-carbonyl]benzene-1,3-diol

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
5.843217391

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.106140580529082

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.531581949406517

> <JCHEM_PKA_STRONGEST_BASIC>
-4.911814105523001

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
140.8105

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,3R,4R,5S)-4-(2,4-dihydroxybenzoyl)-2,5-bis(4-hydroxyphenyl)oxolane-3-carbonyl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.580  -3.215   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.819  -8.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.288  -8.578   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.724  -9.663   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.564  -6.220   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.897  -6.990   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.770  -6.990   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.770  -8.530   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.104  -9.300   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.437  -8.530   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.437  -6.990   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.104  -6.220   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.771  -9.300   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.564  -9.300   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.697  -1.233   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.521  -3.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.201  -5.276   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.346  -6.307   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.810  -5.831   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.130  -4.324   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.986  -3.294   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.306  -1.788   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.955  -6.861   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    5   33                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9                                                            
CONECT   13    3   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18                                                            
CONECT   22   16                                                            
CONECT   23    2   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32   28                                                            
CONECT   33    1   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₉

Average Mass

528.5130 Da

Monoisotopic Mass

528.14203 Da

IUPAC Name

4-[(2S,3R,4R,5S)-4-(2,4-dihydroxybenzoyl)-2,5-bis(4-hydroxyphenyl)oxolane-3-carbonyl]benzene-1,3-diol

Traditional Name

4-[(2S,3R,4R,5S)-4-(2,4-dihydroxybenzoyl)-2,5-bis(4-hydroxyphenyl)oxolane-3-carbonyl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@H]1O[C@@H]([C@@H]([C@H]1C(=O)C1=CC=C(O)C=C1O)C(=O)C1=C(O)C=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H24O9/c31-17-5-1-15(2-6-17)29-25(27(37)21-11-9-19(33)13-23(21)35)26(28(38)22-12-10-20(34)14-24(22)36)30(39-29)16-3-7-18(32)8-4-16/h1-14,25-26,29-36H/t25-,26-,29+,30+/m0/s1

InChI Key

MGYYQYIFNBTUAB-SRPPIYJJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cordia goetzei	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

9,9'-epoxylignans

Alternative Parents

Substituents

7,7p-epoxylignan
7,9p-epoxylignan
9,9p-epoxylignan
Dibenzylbutane lignan skeleton
Alkyl-phenylketone
Phenylketone
Resorcinol
Benzoyl
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Oxolane
Vinylogous acid
Ketone
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	4.22	ALOGPS
logP	5.84	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	140.81 m³·mol⁻¹	ChemAxon
Polarizability	52.91 Å³	ChemAxon
Number of Rings	5	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

17226335

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16066754

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for [Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone (NP0060852)

MOL for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

3D MOL for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

3D SDF for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

3D-SDF for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

PDB for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

3D PDB for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

SMILES for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

INCHI for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

Structure for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)

3D Structure for NP0060852 ([Tetrahydro-2,5-bis(4-hydroxyphenyl)-3,4-furandiyl]bis[(2,4-dihydroxyphenyl)methanone)