NP-MRD: Showing NP-Card for (8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol (NP0326571)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 08:14:53 UTC

Updated at

2022-09-12 08:14:53 UTC

NP-MRD ID

NP0326571

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol

Description

Gomisin O 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. (8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol is found in Schisandra arisanensis, Schisandra chinensis and Schisandra rubriflora. (8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol was first documented in 2005 (PMID: 16238330). Based on a literature review a significant number of articles have been published on Gomisin O (PMID: 17666862) (PMID: 35408515) (PMID: 35350929) (PMID: 30486445) (PMID: 17190445) (PMID: 17611932).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210142D          

 30 33  0  0  1  0            999 V2000
    4.6859    2.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8697    1.8371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393    2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3302    3.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6140    2.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6104    2.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837    1.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    0.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230    1.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8180    3.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    3.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    3.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    3.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226    2.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024    2.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7338    1.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869    0.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773    1.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    3.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6257    4.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419    5.0828    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2215    5.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379    4.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6439    5.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5473    4.1495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3695    4.4027    0.0000 O   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  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    2.0928   -4.7796    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670   -3.5348    0.6124 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7385   -2.4371    0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -2.5421   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2872   -1.4524   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102   -0.2328    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -0.0675    0.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7469    1.1991    1.2232 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4631    1.6974    2.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067   -1.1964    0.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4475   -1.0953    1.5199 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400   -0.8252    0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239    1.1398    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5586    1.6875    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868    3.0373    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    3.8180   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5881    3.2224   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516    1.8622   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889    1.1605   -0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1056    0.6882   -1.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705    4.2087   -0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799    5.3888   -1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4913    5.1831   -0.2625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8228    1.0794    0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1207   -0.2726    0.3821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9085   -1.3051    1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.6439   -0.9018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6382   -1.0205   -1.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -1.8224   -0.9242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3547   -2.2906   -2.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364   -5.5902    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1472   -4.9925    0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043   -4.6135   -0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1267   -3.5044   -0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581    2.1505    2.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094    0.8496    3.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    2.4820    2.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317    0.2837    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715   -1.0581   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5022   -1.3942    1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6472    3.4730    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -0.3967   -1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    1.0324   -2.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0405   -2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997    6.2904   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3797    5.3693   -2.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993    0.9834    2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6350    1.7826    0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2500   -0.2885    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4867   -0.9579    2.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824   -2.2814    1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8614   -1.4979    1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481    0.2699   -1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2561   -1.5340   -2.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2629   -0.1210   -2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3086   -1.7252   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -2.6269   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4869   -3.2788   -2.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 14 15  1  0
 15 16  2  0
 16 23  1  0
 23 22  1  0
 22 21  1  0
 21 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 10  3  1  0
 18 13  1  0
 29  5  1  0
 17 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  6
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  6
 28 54  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  1
 30 58  1  0
 15 41  1  0
 22 45  1  0
 22 46  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END


  Mrv1652309122210142D          

 30 33  0  0  1  0            999 V2000
    4.6859    2.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8697    1.8371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393    2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3302    3.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6140    2.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6104    2.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837    1.2611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527    0.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230    1.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8180    3.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    3.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    3.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    3.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226    2.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024    2.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7338    1.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869    0.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773    1.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    3.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6257    4.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419    5.0828    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2215    5.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379    4.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6439    5.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5473    4.1495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3695    4.4027    0.0000 O   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  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0326571

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC)=C1OC)C1=C(C[C@H](C)[C@H](C)[C@H]2O)C=C2OCOC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O7/c1-11-7-13-8-16-21(30-10-29-16)22(27-5)17(13)18-14(19(24)12(11)2)9-15(25-3)20(26-4)23(18)28-6/h8-9,11-12,19,24H,7,10H2,1-6H3/t11-,12-,19+/m0/s1

> <INCHI_KEY>
GWDFJIBHVSYXQL-SYTFOFBDSA-N

> <FORMULA>
C23H28O7

> <MOLECULAR_WEIGHT>
416.47

> <EXACT_MASS>
416.183503242

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.856141307503584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8R,9S,10S)-3,4,5,19-tetramethoxy-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-8-ol

> <JCHEM_LOGP>
3.4864546446666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.246632639154882

> <JCHEM_PKA_STRONGEST_BASIC>
-3.128322883633655

> <JCHEM_POLAR_SURFACE_AREA>
75.61000000000001

> <JCHEM_REFRACTIVITY>
110.83180000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(8R,9S,10S)-3,4,5,19-tetramethoxy-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-8-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       8.747   3.896   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.223   3.429   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.673   3.944   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.680   5.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.350   6.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.013   5.496   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.006   3.956   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.023   2.354   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.965   0.649   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.336   3.180   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.831   1.574   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.941   0.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.527   5.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.763   7.238   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.777   7.245   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.553   5.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.789   4.577   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.751   4.571   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.370   3.136   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.535   1.547   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.824   3.437   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.228   4.070   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.061   5.601   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.168   8.724   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.505   9.488   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.280  11.076   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.991   9.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.935  10.379   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.755   7.746   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.290   8.218   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
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   18                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16                                                       
CONECT   24   14   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    5   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₇

Average Mass

416.4700 Da

Monoisotopic Mass

416.18350 Da

IUPAC Name

(8R,9S,10S)-3,4,5,19-tetramethoxy-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-8-ol

Traditional Name

(8R,9S,10S)-3,4,5,19-tetramethoxy-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-8-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1OC)C1=C(C[C@H](C)[C@H](C)[C@H]2O)C=C2OCOC2=C1OC

InChI Identifier

InChI=1S/C23H28O7/c1-11-7-13-8-16-21(30-10-29-16)22(27-5)17(13)18-14(19(24)12(11)2)9-15(25-3)20(26-4)23(18)28-6/h8-9,11-12,19,24H,7,10H2,1-6H3/t11-,12-,19+/m0/s1

InChI Key

GWDFJIBHVSYXQL-SYTFOFBDSA-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
Schisandra arisanensis	LOTUS Database	35616633
Schisandra chinensis	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) 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
Benzenoid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	3.49	ChemAxon
pKa (Strongest Acidic)	14.25	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	75.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.83 m³·mol⁻¹	ChemAxon
Polarizability	43.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00029689

Chemspider ID

4476555

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317808

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lei C, Huang SX, Chen JJ, Pu JX, Yang LB, Zhao Y, Liu JP, Gao XM, Xiao WL, Sun HD: Lignans from Schisandra propinqua var. propinqua. Chem Pharm Bull (Tokyo). 2007 Aug;55(8):1281-3. doi: 10.1248/cpb.55.1281. [PubMed:17666862 ]
Sobstyl E, Szopa A, Dziurka M, Ekiert H, Nikolaichuk H, Choma IM: Schisandra rubriflora Fruit and Leaves as Promising New Materials of High Biological Potential: Lignan Profiling and Effect-Directed Analysis. Molecules. 2022 Mar 25;27(7). pii: molecules27072116. doi: 10.3390/molecules27072116. [PubMed:35408515 ]
Ma WH, Lu Y, Huang H, Zhou P, Meng FC, Chen M, Chen DF: Schisanwilsonins H and I, two new dibenzocyclooctane lignans from the fruits of Schisandra wilsoniana. J Asian Nat Prod Res. 2022 Mar 29:1-7. doi: 10.1080/10286020.2022.2054806. [PubMed:35350929 ]
Szopa A, Dziurka M, Warzecha A, Kubica P, Klimek-Szczykutowicz M, Ekiert H: Targeted Lignan Profiling and Anti-Inflammatory Properties of Schisandra rubriflora and Schisandra chinensis Extracts. Molecules. 2018 Nov 27;23(12). pii: molecules23123103. doi: 10.3390/molecules23123103. [PubMed:30486445 ]
Chen M, Kilgore N, Lee KH, Chen DF: Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora. J Nat Prod. 2006 Dec;69(12):1697-701. doi: 10.1021/np060239e. [PubMed:17190445 ]
Coleman RS, Gurrala SR, Mitra S, Raao A: Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products. J Org Chem. 2005 Oct 28;70(22):8932-41. doi: 10.1021/jo051525i. [PubMed:16238330 ]
Huyke C, Engel K, Simon-Haarhaus B, Quirin KW, Schempp CM: Composition and biological activity of different extracts from Schisandra sphenanthera and Schisandra chinensis. Planta Med. 2007 Aug;73(10):1116-26. doi: 10.1055/s-2007-981559. Epub 2007 Jul 5. [PubMed:17611932 ]
LOTUS database [Link]

Showing NP-Card for (8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol (NP0326571)

MOL for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

3D MOL for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

3D SDF for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

3D-SDF for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

PDB for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

3D PDB for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

SMILES for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

INCHI for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

Structure for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)

3D Structure for NP0326571 ((8r,9s,10s)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-8-ol)