NP-MRD: Showing NP-Card for Schisantherin E (NP0140508)

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Record Information

Version

2.0

Created at

2022-06-29 21:37:49 UTC

Updated at

2022-06-29 21:37:49 UTC

NP-MRD ID

NP0140508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Schisantherin E

Description

Schisantherin E 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. Schisantherin E is found in Schisandra rubriflora and Schisandra sphenanthera. Schisantherin E was first documented in 2017 (PMID: 28441491). Based on a literature review a small amount of articles have been published on Schisantherin E (PMID: 33866277) (PMID: 30637977).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223372D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292223372D          

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  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  1  0  0  0
 16 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 13 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  0  0  0  0
  6 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(OC)=C2C(=C1)[C@H](OC(=O)C1=CC=CC=C1)[C@@](C)(O)[C@@H](C)CC1=CC(O)=C(OC)C(OC)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O9/c1-16-13-18-14-20(31)24(35-4)26(37-6)22(18)23-19(15-21(34-3)25(36-5)27(23)38-7)28(30(16,2)33)39-29(32)17-11-9-8-10-12-17/h8-12,14-16,28,31,33H,13H2,1-7H3/t16-,28-,30-/m0/s1

> <INCHI_KEY>
ZNXDFTKQSCEJGE-DSASHONVSA-N

> <FORMULA>
C30H34O9

> <MOLECULAR_WEIGHT>
538.593

> <EXACT_MASS>
538.220282675

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.01036217115393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,9S,10S)-9,14-dihydroxy-3,4,5,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(16),2,4,6,12,14-hexaen-8-yl benzoate

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
4.815938403333332

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.674152679054991

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.93678849688099

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3794834316633056

> <JCHEM_POLAR_SURFACE_AREA>
112.91000000000003

> <JCHEM_REFRACTIVITY>
144.78209999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8S,9S,10S)-9,14-dihydroxy-3,4,5,15,16-pentamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(16),2,4,6,12,14-hexaen-8-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       8.065   8.454   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.144   7.144   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.233   6.055   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.233   4.515   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.720   4.116   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.119   2.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.030   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.543   1.939   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.144   3.426   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.604   3.426   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.205   1.939   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.718   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.629   2.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.028   4.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.515   4.515   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.515   6.055   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.604   7.144   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.469   8.284   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.967   8.723   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.961   6.739   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.145   8.132   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.907   9.470   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.605   8.123   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.157   6.785   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.697   6.776   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.475   8.105   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.712   9.443   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.172   9.452   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.938   2.453   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.515   3.243   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.766   0.048   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.496  -0.920   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.741   0.041   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.405  -1.622   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.516   0.650   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.976  -1.116   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.859   0.032   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      11.423  -0.516   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.729   2.326   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   39                                                  
CONECT    7    6    8   37                                                  
CONECT    8    7    9   35                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16    2   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   13   30                                                       
CONECT   30   29                                                            
CONECT   31   12   32                                                       
CONECT   32   31                                                            
CONECT   33   11   34                                                       
CONECT   34   33                                                            
CONECT   35    8   36                                                       
CONECT   36   35                                                            
CONECT   37    7   38                                                       
CONECT   38   37                                                            
CONECT   39    6                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₉

Average Mass

538.5930 Da

Monoisotopic Mass

538.22028 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(OC)=C2C(=C1)[C@H](OC(=O)C1=CC=CC=C1)[C@@](C)(O)[C@@H](C)CC1=CC(O)=C(OC)C(OC)=C21

InChI Identifier

InChI=1S/C30H34O9/c1-16-13-18-14-20(31)24(35-4)26(37-6)22(18)23-19(15-21(34-3)25(36-5)27(23)38-7)28(30(16,2)33)39-29(32)17-11-9-8-10-12-17/h8-12,14-16,28,31,33H,13H2,1-7H3/t16-,28-,30-/m0/s1

InChI Key

ZNXDFTKQSCEJGE-DSASHONVSA-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 rubriflora	LOTUS Database	35616633
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
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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

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

35308416

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13844274

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yamazoe Y, Tohkin M: Development of template systems for ligand interactions of CYP3A5 and CYP3A7 and their distinctions from CYP3A4 template. Drug Metab Pharmacokinet. 2021 Jun;38:100357. doi: 10.1016/j.dmpk.2020.09.002. Epub 2020 Sep 19. [PubMed:33866277 ]
Xue Y, Li J, Wu Z, Liu G, Tang Y, Li W: Computational insights into the different catalytic activities of CYP3A4 and CYP3A5 toward schisantherin E. Chem Biol Drug Des. 2019 May;93(5):854-864. doi: 10.1111/cbdd.13475. Epub 2019 Feb 5. [PubMed:30637977 ]
Wu JJ, Cao YF, Feng L, He YQ, Hong JY, Dou TY, Wang P, Hao DC, Ge GB, Yang L: A Naturally Occurring Isoform-Specific Probe for Highly Selective and Sensitive Detection of Human Cytochrome P450 3A5. J Med Chem. 2017 May 11;60(9):3804-3813. doi: 10.1021/acs.jmedchem.7b00001. Epub 2017 May 1. [PubMed:28441491 ]

Showing NP-Card for Schisantherin E (NP0140508)

MOL for NP0140508 (Schisantherin E)

3D MOL for NP0140508 (Schisantherin E)

3D SDF for NP0140508 (Schisantherin E)

3D-SDF for NP0140508 (Schisantherin E)

PDB for NP0140508 (Schisantherin E)

3D PDB for NP0140508 (Schisantherin E)

SMILES for NP0140508 (Schisantherin E)

INCHI for NP0140508 (Schisantherin E)

Structure for NP0140508 (Schisantherin E)

3D Structure for NP0140508 (Schisantherin E)