NP-MRD: Showing NP-Card for 6-O-Benzoylgomisin O (NP0070953)

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Record Information

Version

2.0

Created at

2022-04-28 16:21:45 UTC

Updated at

2022-04-28 16:21:45 UTC

NP-MRD ID

NP0070953

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-O-Benzoylgomisin O

Description

Benzoylgomisin O 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. 6-O-Benzoylgomisin O is found in Schisandra propinqua and Schisandra propinqua var.propinqua. 6-O-Benzoylgomisin O was first documented in 2016 (PMID: 29924538). Based on a literature review a small amount of articles have been published on Benzoylgomisin O (PMID: 30486445) (PMID: 33007392).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218212D          

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M  END

     RDKit          3D

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  Mrv1652304282218212D          

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 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
  5 28  1  6  0  0  0
  4 29  1  6  0  0  0
  2 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
  1 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070953

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC)=C1OC)C1=C(C[C@H](C)[C@H](C)[C@H]2OC(=O)C2=CC=CC=C2)C=C2OCOC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O8/c1-16-12-19-13-22-27(37-15-36-22)28(34-5)23(19)24-20(14-21(32-3)26(33-4)29(24)35-6)25(17(16)2)38-30(31)18-10-8-7-9-11-18/h7-11,13-14,16-17,25H,12,15H2,1-6H3/t16-,17-,25+/m0/s1

> <INCHI_KEY>
XUGSROZUUURBSW-XOWTYJCDSA-N

> <FORMULA>
C30H32O8

> <MOLECULAR_WEIGHT>
520.578

> <EXACT_MASS>
520.20971799

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
54.84890830146604

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
5.981754493333334

> <ALOGPS_LOGS>
-5.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.198157570171841

> <JCHEM_POLAR_SURFACE_AREA>
81.68

> <JCHEM_REFRACTIVITY>
140.6538

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.09e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.527  -1.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.763  -0.662   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.168   0.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.505   1.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.991   1.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.755  -0.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.350  -1.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.013  -2.404   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.006  -3.944   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.336  -4.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.673  -3.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.680  -2.416   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.232  -4.493   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.793  -4.151   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.891  -6.313   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.020  -7.460   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.000  -5.549   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.070  -7.178   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.310   0.358   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.050   1.746   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.236   3.053   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.589   1.797   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.315   3.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.854   3.206   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.668   1.899   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.942   0.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.403   0.489   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.949   2.546   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.271   3.231   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.777  -0.655   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.553  -1.986   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.789  -3.323   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.751  -3.329   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.344  -4.789   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.551  -6.416   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.824  -4.463   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.228  -3.830   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.061  -2.299   0.000  0.00  0.00           O+0
CONECT    1    2    8   33                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    1    9                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10   16                                                       
CONECT   16   15                                                            
CONECT   17    9   18                                                       
CONECT   18   17                                                            
CONECT   19    6   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28    5                                                            
CONECT   29    4                                                            
CONECT   30    2   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32    1   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   32   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   31                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₂O₈

Average Mass

520.5780 Da

Monoisotopic Mass

520.20972 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1OC)C1=C(C[C@H](C)[C@H](C)[C@H]2OC(=O)C2=CC=CC=C2)C=C2OCOC2=C1OC

InChI Identifier

InChI=1S/C30H32O8/c1-16-12-19-13-22-27(37-15-36-22)28(34-5)23(19)24-20(14-21(32-3)26(33-4)29(24)35-6)25(17(16)2)38-30(31)18-10-8-7-9-11-18/h7-11,13-14,16-17,25H,12,15H2,1-6H3/t16-,17-,25+/m0/s1

InChI Key

XUGSROZUUURBSW-XOWTYJCDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 propinqua	LOTUS Database	35616633
Schisandra propinqua var.propinqua	Plant	KNApSAcK

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
Benzoate ester
Benzodioxole
Benzoic acid or derivatives
Anisole
Benzoyl
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	5.11	ALOGPS
logP	5.98	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	140.65 m³·mol⁻¹	ChemAxon
Polarizability	54.85 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029810

Chemspider ID

52084592

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91826818

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li W, Song YG, Liu KY, Yang LJ, Liu YL, Su D, Feng YL: [Rapid identification of the different constituents in Fructus Schisandrae Chinensis before and after processing by UHPLC-QTOF/MS~E combining with metabonomics]. Yao Xue Xue Bao. 2016 Sep;51(9):1445-50. [PubMed:29924538 ]
Szopa A, Dziurka M, Warzecha A, Kubica P, Klimek-Szczykutowicz M, Ekiert H: Targeted Lignan Profiling and Anti-Inflammatory Properties of Schisandra rubriflora and Schisandra chinensis Extracts. Molecules. 2018 Nov 27;23(12). pii: molecules23123103. doi: 10.3390/molecules23123103. [PubMed:30486445 ]
Song Y, Shan B, Zeng S, Zhang J, Jin C, Liao Z, Wang T, Zeng Q, He H, Wei F, Ai Z, Su D: Raw and wine processed Schisandra chinensis attenuate anxiety like behavior via modulating gut microbiota and lipid metabolism pathway. J Ethnopharmacol. 2021 Feb 10;266:113426. doi: 10.1016/j.jep.2020.113426. Epub 2020 Sep 29. [PubMed:33007392 ]

Showing NP-Card for 6-O-Benzoylgomisin O (NP0070953)

MOL for NP0070953 (6-O-Benzoylgomisin O)

3D MOL for NP0070953 (6-O-Benzoylgomisin O)

3D SDF for NP0070953 (6-O-Benzoylgomisin O)

3D-SDF for NP0070953 (6-O-Benzoylgomisin O)

PDB for NP0070953 (6-O-Benzoylgomisin O)

3D PDB for NP0070953 (6-O-Benzoylgomisin O)

SMILES for NP0070953 (6-O-Benzoylgomisin O)

INCHI for NP0070953 (6-O-Benzoylgomisin O)

Structure for NP0070953 (6-O-Benzoylgomisin O)

3D Structure for NP0070953 (6-O-Benzoylgomisin O)