NP-MRD: Showing NP-Card for 5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate (NP0215354)

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Record Information

Version

2.0

Created at

2022-09-05 14:57:14 UTC

Updated at

2022-09-05 14:57:14 UTC

NP-MRD ID

NP0215354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate

Description

Kadsufolin C 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. 5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate is found in Kadsura oblongifolia. Kadsufolin C is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509162D          

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M  END

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M  END


  Mrv1533004241509162D          

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    1.7121   -1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3964   -2.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059   -3.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  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  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
  7 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(CC(C)C(C)C(OC(=O)C=CC3=CC=CC=C3)C3=CC(O)=C(OC)C(OC)=C23)=CC2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C31H32O8/c1-17-13-20-14-23-29(38-16-37-23)30(35-4)25(20)26-21(15-22(32)28(34-3)31(26)36-5)27(18(17)2)39-24(33)12-11-19-9-7-6-8-10-19/h6-12,14-15,17-18,27,32H,13,16H2,1-5H3

> <INCHI_KEY>
ZUSDJUTXFWPDCB-UHFFFAOYSA-N

> <FORMULA>
C31H32O8

> <MOLECULAR_WEIGHT>
532.589

> <EXACT_MASS>
532.20971799

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.54196710298289

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
5.25

> <JCHEM_LOGP>
6.374451306666666

> <ALOGPS_LOGS>
-5.69

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.792970871253125

> <JCHEM_PKA_STRONGEST_BASIC>
-4.291795604761982

> <JCHEM_POLAR_SURFACE_AREA>
92.68

> <JCHEM_REFRACTIVITY>
145.9172

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.256  -6.647   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.442  -5.582   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.866  -3.963   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.529  -3.198   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.904  -3.908   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.522  -1.658   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.852  -0.883   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.447   0.603   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.154   1.002   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.792   2.431   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.324   2.589   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.111   3.678   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.518   5.084   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.385   6.331   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.243   7.737   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.660   8.984   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.192   8.826   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.820   7.420   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.917   6.173   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.211   1.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.288   3.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.697   2.345   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.011   3.898   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.034   1.581   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.439   0.095   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.979   0.102   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.755  -1.228   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.263  -1.542   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.430  -3.073   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.026  -3.705   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.991  -2.565   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.451  -2.572   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.453  -4.525   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.304  -5.992   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.675  -1.242   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.189  -1.647   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.196  -3.187   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.473  -4.106   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.678  -5.888   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   36                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    8   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27   32                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   25   36                                                  
CONECT   36   35    7   37                                                  
CONECT   37   36    3   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl 3-phenylprop-2-enoic acid	Generator
5-Hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0,.0,]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₃₁H₃₂O₈

Average Mass

532.5890 Da

Monoisotopic Mass

532.20972 Da

IUPAC Name

5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl 3-phenylprop-2-enoate

Traditional Name

5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2,4,6,12,14(18)-hexaen-8-yl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=C2C(CC(C)C(C)C(OC(=O)C=CC3=CC=CC=C3)C3=CC(O)=C(OC)C(OC)=C23)=CC2=C1OCO2

InChI Identifier

InChI=1S/C31H32O8/c1-17-13-20-14-23-29(38-16-37-23)30(35-4)25(20)26-21(15-22(32)28(34-3)31(26)36-5)27(18(17)2)39-24(33)12-11-19-9-7-6-8-10-19/h6-12,14-15,17-18,27,32H,13,16H2,1-5H3

InChI Key

ZUSDJUTXFWPDCB-UHFFFAOYSA-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 oblongifolia	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
Cinnamic acid ester
Cinnamic acid or derivatives
Benzodioxole
Anisole
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	5.25	ALOGPS
logP	6.37	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-4.3	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	7	ChemAxon
Refractivity	145.92 m³·mol⁻¹	ChemAxon
Polarizability	56.54 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

Not Available

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

74941628

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate (NP0215354)

MOL for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

3D MOL for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

3D SDF for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

3D-SDF for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

PDB for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

3D PDB for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

SMILES for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

INCHI for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

Structure for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)

3D Structure for NP0215354 (5-hydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl 3-phenylprop-2-enoate)