NP-MRD: Showing NP-Card for (9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate (NP0288396)

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Record Information

Version

2.0

Created at

2022-09-09 18:04:42 UTC

Updated at

2022-09-09 18:04:42 UTC

NP-MRD ID

NP0288396

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate

Description

Kadsutherin 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,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate is found in Kadsura coccinea. (9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate was first documented in 2008 (PMID: 19023792). Based on a literature review very few articles have been published on Kadsutherin (PMID: 29861462).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220042D          

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M  END

     RDKit          3D

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  Mrv1652309092220042D          

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M  END
> <DATABASE_ID>
NP0288396

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O7/c1-8-14(2)27(28)34-26-22-18(12-20-24(26)33-13-32-20)10-16(4)15(3)9-17-11-19(29-5)23(30-6)25(31-7)21(17)22/h8,11-12,15-16H,9-10,13H2,1-7H3/b14-8-/t15-,16+/m1/s1

> <INCHI_KEY>
GEOIXWVVEFBXEI-NBWJXOEWSA-N

> <FORMULA>
C27H32O7

> <MOLECULAR_WEIGHT>
468.546

> <EXACT_MASS>
468.21480337

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.29289598801314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,10S)-3,4,5-trimethoxy-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-19-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
6.176056045999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2853652047643465

> <JCHEM_POLAR_SURFACE_AREA>
72.45000000000002

> <JCHEM_REFRACTIVITY>
128.74079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10S)-3,4,5-trimethoxy-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-19-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.815  -0.556   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.662  -1.842   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.200  -1.752   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.047  -3.038   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.890  -0.375   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.428  -0.285   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.032   0.928   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.193   2.878   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.733   2.885   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.497   4.222   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.722   5.552   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.182   5.545   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.417   4.208   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.932   3.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.405   4.568   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.736   3.792   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.729   2.252   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.113   1.557   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.515   2.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.392   1.488   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.499  -0.075   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.705  -1.084   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.938   2.263   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.289   1.667   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.084  -0.196   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.810   6.053   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.046   7.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.042   8.703   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.440   7.795   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.651   9.385   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.777   7.031   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.005   3.908   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.173   2.377   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.769   1.745   0.000  0.00  0.00           O+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   13                                                  
CONECT    9    8   10   34                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   15   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   12                                                       
CONECT   32   10   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    9                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₇

Average Mass

468.5460 Da

Monoisotopic Mass

468.21480 Da

IUPAC Name

(9R,10S)-3,4,5-trimethoxy-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-19-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(9R,10S)-3,4,5-trimethoxy-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-19-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H32O7/c1-8-14(2)27(28)34-26-22-18(12-20-24(26)33-13-32-20)10-16(4)15(3)9-17-11-19(29-5)23(30-6)25(31-7)21(17)22/h8,11-12,15-16H,9-10,13H2,1-7H3/b14-8-/t15-,16+/m1/s1

InChI Key

GEOIXWVVEFBXEI-NBWJXOEWSA-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 coccinea	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
Anisole
Alkyl aryl ether
Fatty acid ester
Fatty acyl
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Ether
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	6.18	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.74 m³·mol⁻¹	ChemAxon
Polarizability	50.29 Å³	ChemAxon
Number of Rings	4	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

C00051115

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

145709744

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lu Y, Chen DF: Kadsutherin D, a new dibenzocyclooctadiene lignan from Kadsura species. Nat Prod Res. 2008;22(15):1344-9. doi: 10.1080/14786410601133525. [PubMed:19023792 ]
Liu JS, Zhang J, Qi YD, Jia XG, Zhang BG, Liu HT: Four New Lignans from Kadsura Interior and Their Bioactivity. Molecules. 2018 May 26;23(6):1279. doi: 10.3390/molecules23061279. [PubMed:29861462 ]
LOTUS database [Link]

Showing NP-Card for (9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate (NP0288396)

MOL for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

PDB for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

Structure for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0288396 ((9r,10s)-3,4,5-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-19-yl (2z)-2-methylbut-2-enoate)