NP-MRD: Showing NP-Card for (9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol (NP0205005)

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Record Information

Version

2.0

Created at

2022-09-05 00:48:58 UTC

Updated at

2022-09-05 00:48:58 UTC

NP-MRD ID

NP0205005

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol

Description

(9R)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]Nonadeca-1(19),2,4,6,12,14(18)-hexaen-9-ol belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. (9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol is found in Schisandra sphenanthera. Based on a literature review very few articles have been published on (9R)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]Nonadeca-1(19),2,4,6,12,14(18)-hexaen-9-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052202492D          

 37 41  0  0  1  0            999 V2000
    4.7128    2.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8805    1.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1187    1.3070    0.0000 O   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


  Mrv1652309052202492D          

 37 41  0  0  1  0            999 V2000
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 27 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205005

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC)=C1OC)C1=C(CC(C)[C@@](C)(O)C2OC2=CC=CC=C2)C=C2OCOC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O8/c1-16-12-17-13-21-25(36-15-35-21)26(33-5)22(17)23-19(14-20(31-3)24(32-4)27(23)34-6)28(29(16,2)30)37-18-10-8-7-9-11-18/h7-11,13-14,16,28,30H,12,15H2,1-6H3/t16?,28?,29-/m1/s1

> <INCHI_KEY>
MSHJHBLTCDLVSX-NDVKFJHLSA-N

> <FORMULA>
C29H32O8

> <MOLECULAR_WEIGHT>
508.567

> <EXACT_MASS>
508.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.44486285623192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol

> <JCHEM_LOGP>
4.739260228666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.678460151536498

> <JCHEM_PKA_STRONGEST_BASIC>
-3.376841529717935

> <JCHEM_POLAR_SURFACE_AREA>
84.84000000000002

> <JCHEM_REFRACTIVITY>
136.54280000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9R)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       8.797   3.766   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.244   3.377   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.673   3.944   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.680   5.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.350   6.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.013   5.496   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.006   3.956   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.088   2.440   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.235   0.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.336   3.180   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.979   1.607   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.188   0.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.527   5.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.763   7.238   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.777   7.245   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.553   5.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.789   4.577   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.751   4.571   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.905   2.992   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.478   1.220   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.824   3.437   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.228   4.070   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.061   5.601   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.168   8.724   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.505   9.488   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.797  10.966   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.991   9.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.286  10.111   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.881  10.727   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.755   7.746   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.381   7.912   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.878   9.360   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.867  10.521   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.367  11.978   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.878  12.273   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.889  11.112   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.390   9.656   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14   18                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16                                                       
CONECT   24   14   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27    5   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂O₈

Average Mass

508.5670 Da

Monoisotopic Mass

508.20972 Da

IUPAC Name

(9R)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol

Traditional Name

(9R)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1OC)C1=C(CC(C)[C@@](C)(O)C2OC2=CC=CC=C2)C=C2OCOC2=C1OC

InChI Identifier

InChI=1S/C29H32O8/c1-16-12-17-13-21-25(36-15-35-21)26(33-5)22(17)23-19(14-20(31-3)24(32-4)27(23)34-6)28(29(16,2)30)37-18-10-8-7-9-11-18/h7-11,13-14,16,28,30H,12,15H2,1-6H3/t16?,28?,29-/m1/s1

InChI Key

MSHJHBLTCDLVSX-NDVKFJHLSA-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
Schisandra sphenanthera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Dibenzocyclooctane lignan
Benzodioxole
Phenoxy compound
Anisole
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	4.74	ChemAxon
pKa (Strongest Acidic)	13.68	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.54 m³·mol⁻¹	ChemAxon
Polarizability	53.44 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

4479592

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321992

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol (NP0205005)

MOL for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

3D MOL for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

3D SDF for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

3D-SDF for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

PDB for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

3D PDB for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

SMILES for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

INCHI for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

Structure for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)

3D Structure for NP0205005 ((9r)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-phenoxy-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-9-ol)