NP-MRD: Showing NP-Card for (9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate (NP0221582)

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Record Information

Version

2.0

Created at

2022-09-05 23:12:14 UTC

Updated at

2022-09-05 23:12:15 UTC

NP-MRD ID

NP0221582

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate

Description

Schisantherin F 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. (9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate is found in Kadsura angustifolia. (9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate was first documented in 2020 (PMID: 30470131). Based on a literature review very few articles have been published on schisantherin F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062201122D          

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M  END

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M  END


  Mrv1652309062201122D          

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 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 16 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221582

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O8/c1-9-13(2)27(30)35-26-20-16(11-19(31-5)24(26)33-7)10-14(3)15(4)22(29)17-12-18(28)23(32-6)25(34-8)21(17)20/h9,11-12,14-15,22,28-29H,10H2,1-8H3/b13-9-/t14-,15-,22+/m1/s1

> <INCHI_KEY>
KFTCQKGLZKQBNY-SEIIMYQLSA-N

> <FORMULA>
C27H34O8

> <MOLECULAR_WEIGHT>
486.561

> <EXACT_MASS>
486.225368055

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.44824694618278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,10R,11S)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.938728654000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.356865894232342

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.768442383934598

> <JCHEM_PKA_STRONGEST_BASIC>
-3.127564449776643

> <JCHEM_POLAR_SURFACE_AREA>
103.68000000000002

> <JCHEM_REFRACTIVITY>
132.85649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10R,11S)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.038  -0.705   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.391  -2.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.886  -2.552   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.314  -4.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.953  -1.442   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.448  -1.810   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.486   0.168   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.028   1.939   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.515   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.356  -0.029   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.639  -1.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.604   2.629   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.227   2.373   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.467   3.364   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.205   4.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.718   4.515   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.629   3.426   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.089   3.426   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.000   4.515   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.488   4.116   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.886   2.629   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.457   2.382   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.797   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.617   0.050   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.051  -0.678   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.690   1.939   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.687   0.696   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.408  -1.056   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   6.055   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.360   6.908   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.089   7.144   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.598   8.654   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.629   7.144   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.364   8.616   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.718   6.055   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16    8   18                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   18   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   19   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   16                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₈

Average Mass

486.5610 Da

Monoisotopic Mass

486.22537 Da

IUPAC Name

(9R,10R,11S)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(9R,10R,11S)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC(=O)C(\C)=C/C)=C1OC)C1=C(C=C(O)C(OC)=C1OC)[C@@H](O)[C@H](C)[C@H](C)C2

InChI Identifier

InChI=1S/C27H34O8/c1-9-13(2)27(30)35-26-20-16(11-19(31-5)24(26)33-7)10-14(3)15(4)22(29)17-12-18(28)23(32-6)25(34-8)21(17)20/h9,11-12,14-15,22,28-29H,10H2,1-8H3/b13-9-/t14-,15-,22+/m1/s1

InChI Key

KFTCQKGLZKQBNY-SEIIMYQLSA-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
Kadsura angustifolia	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) 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
Phenol ester
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
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	4.94	ChemAxon
pKa (Strongest Acidic)	9.77	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.86 m³·mol⁻¹	ChemAxon
Polarizability	51.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00031314

Chemspider ID

23340639

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44567510

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gao D, Qu Y, Wu H: Inhibitory effects of schisantherin F from Schisandra propinqua subsp. sinensis on human melanoma A375 cells through ROS-induced mitochondrial dysfunction and mitochondria-mediated apoptosis. Nat Prod Res. 2020 May;34(10):1486-1489. doi: 10.1080/14786419.2018.1509332. Epub 2018 Nov 23. [PubMed:30470131 ]
LOTUS database [Link]

Showing NP-Card for (9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate (NP0221582)

MOL for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

PDB for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

Structure for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0221582 ((9r,10r,11s)-11,14-dihydroxy-4,5,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaen-3-yl (2z)-2-methylbut-2-enoate)