NP-MRD: Showing NP-Card for viniferal (NP0193640)

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Record Information

Version

2.0

Created at

2022-09-04 11:08:30 UTC

Updated at

2022-09-04 11:08:31 UTC

NP-MRD ID

NP0193640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

viniferal

Description

Viniferal belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. viniferal is found in Upuna borneensis, Vitis ficifolia and Vitis vinifera. viniferal was first documented in 2004 (PMID: 16151870). Based on a literature review a small amount of articles have been published on Viniferal (PMID: 29932064) (PMID: 15730246).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042213082D          

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M  END

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  Mrv1652309042213082D          

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    0.7082    5.5962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4985    4.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4729    2.9265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 18 25  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 26 34  1  0  0  0  0
 15 34  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 36 42  1  0  0  0  0
 35 43  1  0  0  0  0
  6 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1OC2=CC=C(C=O)C=C2[C@H]1C1=CC(O)=CC2=C1[C@@H]([C@H](O2)C1=CC=C(O)C=C1)C1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H26O8/c36-17-18-1-10-29-27(11-18)32(35(42-29)20-4-8-23(38)9-5-20)28-15-26(41)16-30-33(28)31(21-12-24(39)14-25(40)13-21)34(43-30)19-2-6-22(37)7-3-19/h1-17,31-32,34-35,37-41H/t31-,32-,34+,35-/m0/s1

> <INCHI_KEY>
DHTHKPNODOWMKF-VPIGGYNKSA-N

> <FORMULA>
C35H26O8

> <MOLECULAR_WEIGHT>
574.585

> <EXACT_MASS>
574.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
58.96049652326059

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carbaldehyde

> <JCHEM_LOGP>
6.498390006333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.107077230564954

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.582279496707296

> <JCHEM_PKA_STRONGEST_BASIC>
-4.602419004839042

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
159.79089999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
viniferal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       8.848  -1.223   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.441  -0.597   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.281   0.935   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.526   1.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.365   3.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.959   3.998   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.713   3.093   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.874   1.561   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.467   3.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.002   3.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.336   2.752   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.336   1.212   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.670   0.442   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.002   0.442   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.668   1.212   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.668   2.752   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.204   3.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.272   4.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.778   5.013   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.254   6.478   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.761   6.798   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.224   7.622   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.283   7.302   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.313   8.446   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.758   5.837   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.701   1.982   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.241   1.982   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.011   0.649   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.551   0.649   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.321   1.982   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.861   1.982   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.551   3.316   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.011   3.316   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.204   0.736   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.943   5.463   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.037   6.709   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.506   6.548   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.601   7.794   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.227   9.200   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.322  10.446   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.759   9.361   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.664   8.115   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.483   5.463   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   43                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   35                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   34                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18                                                       
CONECT   26   17   27   34                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
CONECT   34   26   15                                                       
CONECT   35    9   36   43                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36                                                       
CONECT   43   35    6                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₂₆O₈

Average Mass

574.5850 Da

Monoisotopic Mass

574.16277 Da

IUPAC Name

(2R,3R)-3-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-carbaldehyde

Traditional Name

viniferal

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1OC2=CC=C(C=O)C=C2[C@H]1C1=CC(O)=CC2=C1[C@@H]([C@H](O2)C1=CC=C(O)C=C1)C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C35H26O8/c36-17-18-1-10-29-27(11-18)32(35(42-29)20-4-8-23(38)9-5-20)28-15-26(41)16-30-33(28)31(21-12-24(39)14-25(40)13-21)34(43-30)19-2-6-22(37)7-3-19/h1-17,31-32,34-35,37-41H/t31-,32-,34+,35-/m0/s1

InChI Key

DHTHKPNODOWMKF-VPIGGYNKSA-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
Upuna borneensis	LOTUS Database	35616633
Vitis ficifolia	LOTUS Database	35616633
Vitis vinifera	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
Neolignan skeleton
1-phenylcoumaran
Stilbene
Coumaran
Resorcinol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Aryl-aldehyde
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	6.5	ChemAxon
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	159.79 m³·mol⁻¹	ChemAxon
Polarizability	58.96 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

C00057975

Chemspider ID

26233612

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Viniferal

METLIN ID

Not Available

PubChem Compound

57518718

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guo R, Wang B, Lin L, Cheng G, Zhou S, Xie S, Shi X, Cao M, Zhang Y, Bai X: Evolutionary, interaction and expression analysis of floral meristem identity genes in inflorescence induction of the second crop in two-crop-a-year grape culture system. J Genet. 2018 Jun;97(2):439-451. [PubMed:29932064 ]
Boddi B, Boka K, Sundqvist C: Tissue specific protochlorophyll(ide) forms in dark-forced shoots of grapevine (Vitis viniferaL.). Photosynth Res. 2004;82(2):141-50. doi: 10.1007/s11120-004-1061-3. [PubMed:16151870 ]
Huang YL, Tsai WJ, Shen CC, Chen CC: Resveratrol derivatives from the roots of Vitis thunbergii. J Nat Prod. 2005 Feb;68(2):217-20. doi: 10.1021/np049686p. [PubMed:15730246 ]
LOTUS database [Link]

Showing NP-Card for viniferal (NP0193640)

MOL for NP0193640 (viniferal)

3D MOL for NP0193640 (viniferal)

3D SDF for NP0193640 (viniferal)

3D-SDF for NP0193640 (viniferal)

PDB for NP0193640 (viniferal)

3D PDB for NP0193640 (viniferal)

SMILES for NP0193640 (viniferal)

INCHI for NP0193640 (viniferal)

Structure for NP0193640 (viniferal)

3D Structure for NP0193640 (viniferal)