NP-MRD: Showing NP-Card for 5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol (NP0324334)

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Record Information

Version

2.0

Created at

2022-09-12 04:21:18 UTC

Updated at

2022-09-12 04:21:18 UTC

NP-MRD ID

NP0324334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol

Description

5-[(2S,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol belongs to the class of organic compounds known as 7,8'-epoxylignans. These are lignans that contain either isomer of the 7,8'-epoxylignan skeleton. The first isomer consists of a tetrahydrofuran that carries a phenyl group at the 2- and the 4-positions, as well as one a methyl group at the 3- and 5-positions. The second isomer consists of a tetrahydrofuran that carries a benzyl group, a phenyl group, and a methyl group at the 2-, 4-, 5-position, respectively. 5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol is found in Parthenocissus tricuspidata. Based on a literature review very few articles have been published on 5-[(2S,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206212D          

 35 39  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309122206212D          

 35 39  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0324334

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O7/c29-19-5-1-15(2-6-19)27-25(17-9-21(31)13-22(32)10-17)26(18-11-23(33)14-24(34)12-18)28(35-27)16-3-7-20(30)8-4-16/h1-14,25-34H/t25-,26-,27+,28+/m0/s1

> <INCHI_KEY>
IRMTUHFNJGIEEV-YVHASNINSA-N

> <FORMULA>
C28H24O7

> <MOLECULAR_WEIGHT>
472.493

> <EXACT_MASS>
472.152203113

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
49.01750593455398

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(2S,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol

> <JCHEM_LOGP>
5.274988944333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.169985188592742

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.742688661081147

> <JCHEM_PKA_STRONGEST_BASIC>
-4.238502219794094

> <JCHEM_POLAR_SURFACE_AREA>
130.61

> <JCHEM_REFRACTIVITY>
130.1377

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2S,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.580  -3.215   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.819  -8.417   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.724  -9.663   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.288  -8.578   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.006  -9.985   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.310  -6.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.521  -3.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.986  -3.294   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.130  -4.324   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.306  -1.788   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.162  -0.757   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.482   0.749   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.697  -1.233   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
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9                                                       
CONECT   16    8   17   25                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   16    6   26                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26                                                       
CONECT   34    5   35                                                       
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₄O₇

Average Mass

472.4930 Da

Monoisotopic Mass

472.15220 Da

IUPAC Name

5-[(2S,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol

Traditional Name

5-[(2S,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H24O7/c29-19-5-1-15(2-6-19)27-25(17-9-21(31)13-22(32)10-17)26(18-11-23(33)14-24(34)12-18)28(35-27)16-3-7-20(30)8-4-16/h1-14,25-34H/t25-,26-,27+,28+/m0/s1

InChI Key

IRMTUHFNJGIEEV-YVHASNINSA-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
Parthenocissus tricuspidata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,8'-epoxylignans. These are lignans that contain either isomer of the 7,8'-epoxylignan skeleton. The first isomer consists of a tetrahydrofuran that carries a phenyl group at the 2- and the 4-positions, as well as one a methyl group at the 3- and 5-positions. The second isomer consists of a tetrahydrofuran that carries a benzyl group, a phenyl group, and a methyl group at the 2-, 4-, 5-position, respectively.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,8'-epoxylignans

Alternative Parents

Substituents

7,8p-epoxylignan
7,7p-epoxylignan
Dibenzylbutane lignan skeleton
Stilbene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	5.27	ChemAxon
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.14 m³·mol⁻¹	ChemAxon
Polarizability	49.02 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	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

162922054

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol (NP0324334)

MOL for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

3D MOL for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

3D SDF for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

3D-SDF for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

PDB for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

3D PDB for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

SMILES for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

INCHI for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

Structure for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)

3D Structure for NP0324334 (5-[(2s,3r,4r,5s)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol)