NP-MRD: Showing NP-Card for Benzoylgomisin H (NP0077889)

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Record Information

Version

2.0

Created at

2022-04-28 23:02:02 UTC

Updated at

2022-04-28 23:02:02 UTC

NP-MRD ID

NP0077889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Benzoylgomisin H

Description

Benzoylgomisin H 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) 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. Benzoylgomisin H is found in Schisandra chinensis . Benzoylgomisin H was first documented in 2009 (PMID: 19259942). Based on a literature review very few articles have been published on Benzoylgomisin H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201022D          

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M  END

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 13 14  1  0  0  0  0
 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
  5 19  1  6  0  0  0
  5 20  1  1  0  0  0
  4 21  1  6  0  0  0
  2 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
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 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
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  1  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC(=O)C3=CC=CC=C3)=C1OC)C1=C(C[C@](C)(O)[C@@H](C)C2)C=C(OC)C(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O8/c1-17-13-19-14-21(33-3)26(36-6)28(38-29(31)18-11-9-8-10-12-18)23(19)24-20(16-30(17,2)32)15-22(34-4)25(35-5)27(24)37-7/h8-12,14-15,17,32H,13,16H2,1-7H3/t17-,30-/m0/s1

> <INCHI_KEY>
AZQOQICAWOAGEN-ZOKDDAQRSA-N

> <FORMULA>
C30H34O8

> <MOLECULAR_WEIGHT>
522.594

> <EXACT_MASS>
522.225368055

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.4325830528828

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S,10S)-10-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl benzoate

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
5.2046354359999984

> <ALOGPS_LOGS>
-5.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.638807509277221

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9567855954421427

> <JCHEM_POLAR_SURFACE_AREA>
92.68

> <JCHEM_REFRACTIVITY>
143.5746

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10S)-10-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.144  -1.886   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.233  -2.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.233  -4.515   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.144  -5.604   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.604  -5.604   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.515  -4.515   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.515  -2.975   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.604  -1.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.205  -0.399   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.718  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.629  -1.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.028  -2.576   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.936  -1.198   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.431  -2.059   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.184   0.910   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.566   1.351   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.038   1.114   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.291   2.451   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.310  -6.614   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.886  -7.218   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.096  -6.912   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.720  -2.576   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.119  -1.089   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.030  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.543  -0.399   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.901   0.988   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.278   2.704   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.525   3.745   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.899   3.473   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.399   3.124   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.347   4.249   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.795   5.722   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.294   6.071   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.347   4.947   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.384   0.986   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.670   1.988   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.797  -1.103   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      13.170  -1.941   0.000  0.00  0.00           C+0
CONECT    1    2    8   25                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6   19   20                                             
CONECT    6    5    7                                                       
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    5                                                            
CONECT   20    5                                                            
CONECT   21    4                                                            
CONECT   22    2   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25   35                                                  
CONECT   25   24    1   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   24   36                                                       
CONECT   36   35                                                            
CONECT   37   23   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₈

Average Mass

522.5940 Da

Monoisotopic Mass

522.22537 Da

IUPAC Name

(9S,10S)-10-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl benzoate

Traditional Name

(9S,10S)-10-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl benzoate

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC(=O)C3=CC=CC=C3)=C1OC)C1=C(C[C@](C)(O)[C@@H](C)C2)C=C(OC)C(OC)=C1OC

InChI Identifier

InChI=1S/C30H34O8/c1-17-13-19-14-21(33-3)26(36-6)28(38-29(31)18-11-9-8-10-12-18)23(19)24-20(16-30(17,2)32)15-22(34-4)25(35-5)27(24)37-7/h8-12,14-15,17,32H,13,16H2,1-7H3/t17-,30-/m0/s1

InChI Key

AZQOQICAWOAGEN-ZOKDDAQRSA-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 chinensis	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) 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
Phenol ester
Benzoic acid or derivatives
Phenol ether
Benzoyl
Anisole
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Carboxylic acid ester
Ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	4.57	ALOGPS
logP	5.2	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	14.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	143.57 m³·mol⁻¹	ChemAxon
Polarizability	55.43 Å³	ChemAxon
Number of Rings	4	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

C00041374

Chemspider ID

52084072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14992069

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shi P, He Q, Zhang Y, Qu H, Cheng Y: Characterisation and identification of isomeric dibenzocyclooctadiene lignans from Schisandra Chinensis by high-performance liquid chromatography combined with electrospray ionisation tandem mass spectrometry. Phytochem Anal. 2009 May-Jun;20(3):197-206. doi: 10.1002/pca.1115. [PubMed:19259942 ]

Showing NP-Card for Benzoylgomisin H (NP0077889)

MOL for NP0077889 (Benzoylgomisin H)

3D MOL for NP0077889 (Benzoylgomisin H)

3D SDF for NP0077889 (Benzoylgomisin H)

3D-SDF for NP0077889 (Benzoylgomisin H)

PDB for NP0077889 (Benzoylgomisin H)

3D PDB for NP0077889 (Benzoylgomisin H)

SMILES for NP0077889 (Benzoylgomisin H)

INCHI for NP0077889 (Benzoylgomisin H)

Structure for NP0077889 (Benzoylgomisin H)

3D Structure for NP0077889 (Benzoylgomisin H)