NP-MRD: Showing NP-Card for (11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate (NP0298340)

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Record Information

Version

2.0

Created at

2022-09-10 09:31:29 UTC

Updated at

2022-09-10 09:31:29 UTC

NP-MRD ID

NP0298340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate

Description

Schisantherin L 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. (11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate is found in Kadsura angustifolia and Kadsura coccinea. Based on a literature review very few articles have been published on schisantherin L.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102211312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102211312D          

 36 40  0  0  1  0            999 V2000
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 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  6  0  0  0
 12 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 11 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OCOC2=CC2=C1C1=C(OC)C3=C(OCO3)C=C1[C@H](OC(=O)C(\C)=C/C)[C@@H](C)[C@@H](C)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O9/c1-7-12(2)27(29)36-22-14(4)13(3)21(28)15-8-17-23(34-10-32-17)25(30-5)19(15)20-16(22)9-18-24(26(20)31-6)35-11-33-18/h7-9,13-14,21-22,28H,10-11H2,1-6H3/b12-7-/t13-,14+,21-,22-/m1/s1

> <INCHI_KEY>
JTLHKPZZCOQRTA-NJVXVFQPSA-N

> <FORMULA>
C27H30O9

> <MOLECULAR_WEIGHT>
498.528

> <EXACT_MASS>
498.188982546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.860772332629615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11R,12S,13R,14R)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0^{2,10}.0^{4,8}.0^{17,21}]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.4851105413333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.225516930375782

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1375588946536315

> <JCHEM_POLAR_SURFACE_AREA>
101.91000000000003

> <JCHEM_REFRACTIVITY>
128.9406

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(11R,12S,13R,14R)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0^{2,10}.0^{4,8}.0^{17,21}]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      11.403  10.625   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.166  11.962   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.389  13.292   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.152  14.629   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.849  13.284   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.072  14.614   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.067  11.914   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.668  11.076   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.668   9.536   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.155   9.138   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.554   7.650   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.465   6.561   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.978   6.960   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.468   5.158   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.825   3.526   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.579   8.447   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.039   8.447   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.950   9.536   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.462   9.138   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.064   7.650   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.153   6.561   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.640   6.960   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.603   5.720   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.266   4.007   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.454   5.189   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.933   5.430   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.692   6.951   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.950  11.076   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.627  11.962   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.039  12.165   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.540  13.668   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.579  12.165   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.051  13.749   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.164   5.189   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.685   5.430   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.926   6.951   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   32                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13   34                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13    9   17                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   17   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   20                                                       
CONECT   28   18   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    8   33                                                  
CONECT   33   32                                                            
CONECT   34   12   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   11                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₉

Average Mass

498.5280 Da

Monoisotopic Mass

498.18898 Da

IUPAC Name

(11R,12S,13R,14R)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0^{2,10}.0^{4,8}.0^{17,21}]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(11R,12S,13R,14R)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0^{2,10}.0^{4,8}.0^{17,21}]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=C2OCOC2=CC2=C1C1=C(OC)C3=C(OCO3)C=C1[C@H](OC(=O)C(\C)=C/C)[C@@H](C)[C@@H](C)[C@H]2O

InChI Identifier

InChI=1S/C27H30O9/c1-7-12(2)27(29)36-22-14(4)13(3)21(28)15-8-17-23(34-10-32-17)25(30-5)19(15)20-16(22)9-18-24(26(20)31-6)35-11-33-18/h7-9,13-14,21-22,28H,10-11H2,1-6H3/b12-7-/t13-,14+,21-,22-/m1/s1

InChI Key

JTLHKPZZCOQRTA-NJVXVFQPSA-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
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
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Ether
Acetal
Organoheterocyclic compound
Carbonyl group
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	4.49	ChemAxon
pKa (Strongest Acidic)	14.23	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.94 m³·mol⁻¹	ChemAxon
Polarizability	51.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040252

Chemspider ID

8181665

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10006085

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate (NP0298340)

MOL for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

PDB for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

Structure for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0298340 ((11r,12s,13r,14r)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2,4(8),9,16,21-hexaen-11-yl (2z)-2-methylbut-2-enoate)