NP-MRD: Showing NP-Card for (1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate (NP0197439)

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Record Information

Version

2.0

Created at

2022-09-04 15:42:06 UTC

Updated at

2022-09-04 15:42:06 UTC

NP-MRD ID

NP0197439

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate

Description

Heteroclitin D 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. (1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate is found in Kadsura heteroclita and Kadsura interior. (1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate was first documented in 2006 (PMID: 17135051). Based on a literature review a significant number of articles have been published on Heteroclitin D (PMID: 19023792) (PMID: 35039063) (PMID: 26179842) (PMID: 25331257) (PMID: 29403855).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217422D          

 35 39  0  0  1  0            999 V2000
    5.0682    5.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9671    5.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7893    6.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    4.9021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042217422D          

 35 39  0  0  1  0            999 V2000
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 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  1  0  0  0
 12 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197439

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(=O)[C@]23COC4=C2C(=CC2=C4OCO2)[C@@H](OC(=O)C(\C)=C/C)[C@H](C)[C@H](C)CC3=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O8/c1-7-13(2)26(29)35-21-15(4)14(3)8-16-9-18(30-5)23(31-6)25(28)27(16)11-32-24-20(27)17(21)10-19-22(24)34-12-33-19/h7,9-10,14-15,21H,8,11-12H2,1-6H3/b13-7-/t14-,15-,21+,27+/m1/s1

> <INCHI_KEY>
CGWKMZYZZCWGCK-DITIAMETSA-N

> <FORMULA>
C27H30O8

> <MOLECULAR_WEIGHT>
482.529

> <EXACT_MASS>
482.194067926

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.1971947843172

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,12S,13R,14R)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0^{1,16}.0^{4,21}.0^{5,9}]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.912731141666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.291723988189542

> <JCHEM_POLAR_SURFACE_AREA>
89.52000000000001

> <JCHEM_REFRACTIVITY>
129.82189999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,13R,14R)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0^{1,16}.0^{4,21}.0^{5,9}]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       9.461   9.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.272  11.006   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.854  11.607   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.665  13.135   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.625  10.679   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.207  11.280   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.813   9.150   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.584   8.223   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.971   6.732   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.511   6.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.270   5.380   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.489   4.053   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.949   4.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.190   5.405   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.699   5.018   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.606   3.481   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.039   2.918   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.809   3.483   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.071   2.600   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.785   2.256   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.780   0.716   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.444  -0.050   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.799   3.451   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.672   2.998   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.016   1.496   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.948   5.066   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.372   5.799   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.985   7.290   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.766   8.617   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.838   9.846   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.257   9.004   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.470  10.529   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.510   2.900   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.922   3.515   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.774   5.048   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   31                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16   18   27                                             
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   15   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    8   32                                                  
CONECT   32   31                                                            
CONECT   33   12   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   11                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₈

Average Mass

482.5290 Da

Monoisotopic Mass

482.19407 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(=O)[C@]23COC4=C2C(=CC2=C4OCO2)[C@@H](OC(=O)C(\C)=C/C)[C@H](C)[C@H](C)CC3=C1

InChI Identifier

InChI=1S/C27H30O8/c1-7-13(2)26(29)35-21-15(4)14(3)8-16-9-18(30-5)23(31-6)25(28)27(16)11-32-24-20(27)17(21)10-19-22(24)34-12-33-19/h7,9-10,14-15,21H,8,11-12H2,1-6H3/b13-7-/t14-,15-,21+,27+/m1/s1

InChI Key

CGWKMZYZZCWGCK-DITIAMETSA-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 heteroclita	LOTUS Database	35616633
Kadsura interior	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
Benzodioxole
Coumaran
Alkyl aryl ether
Fatty acid ester
Fatty acyl
Benzenoid
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Acetal
Carboxylic acid derivative
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Aldehyde
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024179

Chemspider ID

20576761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16745528

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 ]
Xu J, Liu J, Li B, Wei X, Qi Y, Zhang B, Liu H, Xiao P: Comparison of blood tonic efficacy and chemical constituents of Kadsura interior A.C. Smith and its closely related species. Chin Med. 2022 Jan 17;17(1):14. doi: 10.1186/s13020-021-00544-w. [PubMed:35039063 ]
Chen M, Jia ZW, Chen DF: Heteroclitin H, a new lignan from Kadsura heteroclita. J Asian Nat Prod Res. 2006 Oct-Nov;8(7):643-8. doi: 10.1080/10286020500209053. [PubMed:17135051 ]
Li H, Li W, Yu M, Jiang L: LC-MS/MS determination of 1-O-acetylbritannilactone in rat plasma and its application to a preclinical pharmacokinetic study. Biomed Chromatogr. 2016 Mar;30(3):419-25. doi: 10.1002/bmc.3564. Epub 2015 Aug 31. [PubMed:26179842 ]
Zhang F, Zhang N, Pang L, Tan Y, Xu H: Quantification of heteroclitin D in rat plasma: validation of an LC/MS/MS method and its application in a preclinical pharmacokinetic study. Biomed Chromatogr. 2015 May;29(5):756-61. doi: 10.1002/bmc.3352. Epub 2014 Oct 21. [PubMed:25331257 ]
Yu XX, Wang QW, Xu XJ, Lv WJ, Zhao MQ, Liang ZK: Preparative isolation of Heteroclitin D from Kadsurae Caulis using normal-phase flash chromatography. J Pharm Anal. 2013 Dec;3(6):456-459. doi: 10.1016/j.jpha.2013.07.004. Epub 2013 Aug 7. [PubMed:29403855 ]
LOTUS database [Link]

Showing NP-Card for (1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate (NP0197439)

MOL for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

PDB for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

Structure for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0197439 ((1s,12s,13r,14r)-18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl (2z)-2-methylbut-2-enoate)