NP-MRD: Showing NP-Card for (1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol (NP0248640)

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Record Information

Version

2.0

Created at

2022-09-07 10:58:14 UTC

Updated at

2022-09-07 10:58:14 UTC

NP-MRD ID

NP0248640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol

Description

ZINC33831490 belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. (1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol is found in Gnetum hainanense, Gnetum klossii, Gnetum parvifolium and Gnetum ula. Based on a literature review very few articles have been published on ZINC33831490.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072212582D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072212582D          

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 26 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
  5 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C2\[C@@H]([C@H](C3=C(O)C=C(O)C=C23)C2=CC=C(O)C(OC)=C2)C2=CC(O)=CC(O)=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O8/c1-37-26-8-15(3-5-23(26)34)7-21-22-13-20(33)14-25(36)30(22)29(16-4-6-24(35)27(11-16)38-2)28(21)17-9-18(31)12-19(32)10-17/h3-14,28-29,31-36H,1-2H3/b21-7+/t28-,29+/m0/s1

> <INCHI_KEY>
YUGHGAXRXHODHK-VEJRHNPISA-N

> <FORMULA>
C30H26O8

> <MOLECULAR_WEIGHT>
514.53

> <EXACT_MASS>
514.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
53.8008902504787

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z,2S,3S)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydro-1H-indene-4,6-diol

> <JCHEM_LOGP>
5.367088619666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.338300578191392

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.850727069327647

> <JCHEM_PKA_STRONGEST_BASIC>
-4.591981896107929

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
143.13279999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1Z,2S,3S)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.754   4.201   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.723   3.056   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.217   3.376   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.187   2.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.680   2.552   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.222  -8.407   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.839  -6.118   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.400  -3.970   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.204   4.017   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.235   5.161   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.741   4.841   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.772   5.985   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   17                                                       
CONECT   26   16    7   27                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
CONECT   35    5   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₈

Average Mass

514.5300 Da

Monoisotopic Mass

514.16277 Da

IUPAC Name

(1Z,2S,3S)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydro-1H-indene-4,6-diol

Traditional Name

(1Z,2S,3S)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C2\[C@@H]([C@H](C3=C(O)C=C(O)C=C23)C2=CC=C(O)C(OC)=C2)C2=CC(O)=CC(O)=C2)=CC=C1O

InChI Identifier

InChI=1S/C30H26O8/c1-37-26-8-15(3-5-23(26)34)7-21-22-13-20(33)14-25(36)30(22)29(16-4-6-24(35)27(11-16)38-2)28(21)17-9-18(31)12-19(32)10-17/h3-14,28-29,31-36H,1-2H3/b21-7+/t28-,29+/m0/s1

InChI Key

YUGHGAXRXHODHK-VEJRHNPISA-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
Gnetum hainanense	LOTUS Database	35616633
Gnetum klossii	LOTUS Database	35616633
Gnetum parvifolium	LOTUS Database	35616633
Gnetum ula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Indane
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Resorcinol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.37	ChemAxon
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	143.13 m³·mol⁻¹	ChemAxon
Polarizability	53.8 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

4476542

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317791

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol (NP0248640)

MOL for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

3D MOL for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

3D SDF for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

3D-SDF for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

PDB for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

3D PDB for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

SMILES for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

INCHI for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

Structure for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)

3D Structure for NP0248640 ((1z,2s,3s)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol)