NP-MRD: Showing NP-Card for (9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene (NP0226812)

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Record Information

Version

2.0

Created at

2022-09-06 05:58:11 UTC

Updated at

2022-09-06 05:58:11 UTC

NP-MRD ID

NP0226812

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene

Description

Deoxyschisandrin, also known as schizandrin a, 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. (9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene is found in Kadsura coccinea, Kadsura interior, Schisandra chinensis, Schisandra henryi and Schisandra rubriflora. Based on a literature review very few articles have been published on Deoxyschisandrin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207582D          

 30 32  0  0  1  0            999 V2000
    4.6065    1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8891    1.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886    2.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    1.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531    0.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661   -0.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9525    0.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    1.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7969    2.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8961    1.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6105    1.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333    0.0951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028   -0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    0.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -0.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    3.8271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2566    4.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    3.8271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7352    4.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    3.2438    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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
M  END


  Mrv1652309062207582D          

 30 32  0  0  1  0            999 V2000
    4.6065    1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8891    1.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886    2.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    1.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531    0.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661   -0.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9525    0.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    1.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7969    2.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8961    1.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6105    1.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333    0.0951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028   -0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    0.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -0.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    3.8271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2566    4.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    3.8271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7352    4.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    3.2438    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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226812

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-13-9-15-11-17(25-3)21(27-5)23(29-7)19(15)20-16(10-14(13)2)12-18(26-4)22(28-6)24(20)30-8/h11-14H,9-10H2,1-8H3/t13-,14-/m0/s1

> <INCHI_KEY>
JEJFTTRHGBKKEI-KBPBESRZSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.914054218431374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaene

> <JCHEM_LOGP>
4.700735982666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.151535083537236

> <JCHEM_POLAR_SURFACE_AREA>
55.38000000000001

> <JCHEM_REFRACTIVITY>
116.55279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaene

> <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       8.599   3.483   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.260   2.598   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.604   2.629   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.205   4.116   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.718   4.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.629   3.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.028   1.939   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.526   0.007   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.923  -1.576   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.515   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.511   0.191   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.955  -0.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.089   3.426   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000   4.515   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.488   4.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.886   2.629   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.539   2.587   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.873   3.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.797   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.742   0.178   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.179  -0.541   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.690   1.939   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.194   0.354   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.522  -1.078   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   6.055   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.089   7.144   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.479   8.624   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.629   7.144   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.239   8.624   0.000  0.00  0.00           C+0
HETATM   30  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   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14   22                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   13   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   14   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    5                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Schizandrin a	MeSH
Schisandrin a	MeSH
Deoxyschizandrin	MeSH

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

(9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaene

Traditional Name

(9S,10S)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0^{2,7}]hexadeca-1(12),2(7),3,5,13,15-hexaene

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H32O6/c1-13-9-15-11-17(25-3)21(27-5)23(29-7)19(15)20-16(10-14(13)2)12-18(26-4)22(28-6)24(20)30-8/h11-14H,9-10H2,1-8H3/t13-,14-/m0/s1

InChI Key

JEJFTTRHGBKKEI-KBPBESRZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Kadsura coccinea	LOTUS Database	35616633
Kadsura interior	LOTUS Database	35616633
Schisandra chinensis	LOTUS Database	35616633
Schisandra henryi	LOTUS Database	35616633
Schisandra rubriflora	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 ether
Anisole
Alkyl aryl ether
Benzenoid
Ether
Organic oxygen compound
Hydrocarbon derivative
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	4.7	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.55 m³·mol⁻¹	ChemAxon
Polarizability	45.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00041495

Chemspider ID

7977768

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9802006

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene (NP0226812)

MOL for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

3D MOL for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

3D SDF for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

3D-SDF for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

PDB for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

3D PDB for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

SMILES for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

INCHI for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

Structure for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)

3D Structure for NP0226812 ((9s,10s)-3,4,5,14,15,16-hexamethoxy-9,10-dimethyltricyclo[10.4.0.0²,⁷]hexadeca-1(12),2(7),3,5,13,15-hexaene)