NP-MRD: Showing NP-Card for (5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione (NP0201213)

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Record Information

Version

2.0

Created at

2022-09-04 20:12:54 UTC

Updated at

2022-09-04 20:12:54 UTC

NP-MRD ID

NP0201213

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione

Description

Prunolide C 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. (5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione was first documented in 2022 (PMID: 35050597). Based on a literature review very few articles have been published on Prunolide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042222122D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042222122D          

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    3.5011    5.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091    6.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6800    4.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719    4.1065    0.0000 C   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
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  0  0  0
  2 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 15 28  1  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
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 29 35  1  0  0  0  0
 28 36  2  0  0  0  0
 12 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 37 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201213

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=CC(=O)O[C@]11O[C@]2(OC(=O)C=C2C2=CC=C(O)C=C2)C(=C1C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H22O9/c35-23-9-1-19(2-10-23)27-17-29(39)41-33(27)31(21-5-13-25(37)14-6-21)32(22-7-15-26(38)16-8-22)34(43-33)28(18-30(40)42-34)20-3-11-24(36)12-4-20/h1-18,35-38H/t33-,34-/m0/s1

> <INCHI_KEY>
TVZMJJGJCOWLNQ-HEVIKAOCSA-N

> <FORMULA>
C34H22O9

> <MOLECULAR_WEIGHT>
574.541

> <EXACT_MASS>
574.126382288

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
57.32548168821569

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,7R)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4^{7}.2^{5}]trideca-3,10,12-triene-2,9-dione

> <JCHEM_LOGP>
7.180124560333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.981143192229075

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.555126599635706

> <JCHEM_PKA_STRONGEST_BASIC>
-4.668953787999376

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
155.0409

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5R,7R)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4^{7}.2^{5}]trideca-3,10,12-triene-2,9-dione

> <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       7.277   5.236   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.747   5.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.989   3.721   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.480   4.027   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.345   2.986   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.679   1.483   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.544   0.442   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.075   0.904   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.060  -0.136   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.259   2.408   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.876   3.449   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.305   5.557   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.706   6.196   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.086   5.038   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.863   6.053   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.503   4.652   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.368   3.611   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.767   2.570   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.973   4.369   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.667   5.878   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.708   7.013   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.211   6.679   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.252   7.814   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.789   9.283   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.830  10.418   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.286   9.617   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.245   8.482   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.621   7.394   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.982   8.795   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.551   8.942   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.190  10.343   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.296  11.597   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.936  12.998   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.237  11.450   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.876  10.049   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.130   7.087   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.265   8.128   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.931   9.631   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.066  10.672   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.535  10.210   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.670  11.251   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.869   8.706   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.734   7.665   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    4   13   14   36                                             
CONECT   13   12    2                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   20   28                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
CONECT   28   15   29   36                                                  
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29                                                       
CONECT   36   28   12   37                                                  
CONECT   37   36   38   43                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   37                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₂₂O₉

Average Mass

574.5410 Da

Monoisotopic Mass

574.12638 Da

IUPAC Name

(5R,7R)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4^{7}.2^{5}]trideca-3,10,12-triene-2,9-dione

Traditional Name

(5R,7R)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4^{7}.2^{5}]trideca-3,10,12-triene-2,9-dione

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=CC(=O)O[C@]11O[C@]2(OC(=O)C=C2C2=CC=C(O)C=C2)C(=C1C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C34H22O9/c35-23-9-1-19(2-10-23)27-17-29(39)41-33(27)31(21-5-13-25(37)14-6-21)32(22-7-15-26(38)16-8-22)34(43-33)28(18-30(40)42-34)20-3-11-24(36)12-4-20/h1-18,35-38H/t33-,34-/m0/s1

InChI Key

TVZMJJGJCOWLNQ-HEVIKAOCSA-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

Not Available

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
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Monocyclic benzene moiety
2-furanone
Dicarboxylic acid or derivatives
Benzenoid
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen 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	7.18	ChemAxon
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	155.04 m³·mol⁻¹	ChemAxon
Polarizability	57.33 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

Not Available

Chemspider ID

10208270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21589556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Holland DC, Prebble DW, Er S, Hayton JB, Robertson LP, Avery VM, Domanskyi A, Kiefel MJ, Hooper JNA, Carroll AR: alpha-Synuclein Aggregation Inhibitory Prunolides and a Dibrominated beta-Carboline Sulfamate from the Ascidian Synoicum prunum. J Nat Prod. 2022 Feb 25;85(2):441-452. doi: 10.1021/acs.jnatprod.1c01172. Epub 2022 Jan 20. [PubMed:35050597 ]
LOTUS database [Link]

Showing NP-Card for (5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione (NP0201213)

MOL for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

3D MOL for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

3D SDF for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

3D-SDF for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

PDB for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

3D PDB for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

SMILES for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

INCHI for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

Structure for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)

3D Structure for NP0201213 ((5r,7r)-4,11,12,13-tetrakis(4-hydroxyphenyl)-1,6,8-trioxadispiro[4.1.4⁷.2⁵]trideca-3,10,12-triene-2,9-dione)