NP-MRD: Showing NP-Card for Gomisin N (NP0054888)

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Record Information

Version

2.0

Created at

2022-04-28 01:05:47 UTC

Updated at

2022-04-28 01:05:47 UTC

NP-MRD ID

NP0054888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gomisin N

Description

(+)-Schisandrin B, also known as gamma-schizandrin or schizandrin b, 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 (+)-schisandrin B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Gomisin N is found in Kadsura coccinea, Schisandra chinensis , Schisandra lancifolia and Schisandra propinqua. Gomisin N was first documented in 2021 (PMID: 35194448). Based on a literature review a small amount of articles have been published on (+)-schisandrin B (PMID: 35419003) (PMID: 35405150) (PMID: 35215943) (PMID: 35157912).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203052D          

 29 32  0  0  1  0            999 V2000
    2.9341   -3.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7300   -2.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463   -3.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633   -4.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2540   -4.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4580   -5.1343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7417   -4.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5247   -3.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6997   -3.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2841   -3.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935   -2.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5728   -1.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1388   -1.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866   -2.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4764   -3.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3359   -5.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899   -5.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590   -2.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1554   -2.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391   -1.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264   -2.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590   -1.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9524   -0.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -0.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1960   -0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7806   -2.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
  6 18  1  1  0  0  0
  5 19  1  1  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    5.2417   -1.1478    0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4725   -0.0088    0.2298 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0882    0.0064    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4131   -1.1833    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0443   -1.2254    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3896   -0.0114    0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040    1.1902   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2065    2.2847   -0.2768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2256    2.7344   -1.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3812    1.1930   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176    2.3485   -0.2390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5374    2.7655   -1.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0366    0.3420    0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1594   -0.2123   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434    0.4192   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4338    1.5672    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2905    2.0893    1.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    1.4707    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1075    1.8671    1.5651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    1.4533    2.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258    3.2285    1.8327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9396    3.5973    1.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4756    2.4248    0.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3200   -1.4319   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098   -2.2288   -1.2974 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1640   -3.2034   -2.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -2.9831   -0.0939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8615   -3.0623    0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5784   -2.6073    0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2386   -1.4882    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2943   -0.9069    0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511   -1.9753   -0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9726   -2.1064    0.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788    3.7781   -1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0704    2.0184   -2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312    2.7559   -1.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266    2.3526   -2.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4760    3.8583   -1.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324    2.3518   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2366    0.0061   -0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830    1.1888    3.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0436    2.2483    3.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029    0.5278    2.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454    4.3514    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5458    3.9465    2.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939   -2.1057   -0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5830   -1.1119   -2.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1639   -1.5667   -1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545   -3.6928   -2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365   -3.9327   -2.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1271   -2.6462   -3.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927   -4.0646   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5822   -3.6273    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560   -3.6996    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2251   -2.0893    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3680   -2.7663    1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128   -3.2803    0.4266 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
 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 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  6
 26 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  6
 28 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 15 40  1  0
 22 44  1  0
 22 45  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
M  END


  Mrv1652304282203052D          

 29 32  0  0  1  0            999 V2000
    2.9341   -3.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7300   -2.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463   -3.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633   -4.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2540   -4.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4580   -5.1343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7417   -4.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5247   -3.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6997   -3.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2841   -3.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935   -2.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5728   -1.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1388   -1.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866   -2.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4764   -3.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3359   -5.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899   -5.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590   -2.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1554   -2.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391   -1.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264   -2.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590   -1.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9524   -0.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -0.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1960   -0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7806   -2.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
  6 18  1  1  0  0  0
  5 19  1  1  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC)=C1OC)C1=C(C[C@H](C)[C@H](C)C2)C=C2OCOC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O6/c1-12-7-14-9-16(24-3)20(25-4)22(26-5)18(14)19-15(8-13(12)2)10-17-21(23(19)27-6)29-11-28-17/h9-10,12-13H,7-8,11H2,1-6H3/t12-,13+/m1/s1

> <INCHI_KEY>
RTZKSTLPRTWFEV-OLZOCXBDSA-N

> <FORMULA>
C23H28O6

> <MOLECULAR_WEIGHT>
400.471

> <EXACT_MASS>
400.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.35232934633264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2,4,6,12,14(18)-hexaene

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
4.639311981666667

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.196413763613773

> <JCHEM_POLAR_SURFACE_AREA>
55.38000000000001

> <JCHEM_REFRACTIVITY>
109.39329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2,4,6,12,14(18)-hexaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.477  -5.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.963  -5.592   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.300  -6.356   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.705  -7.842   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.941  -9.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.455  -9.584   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.118  -8.820   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.713  -7.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.173  -7.341   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.397  -6.011   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.161  -4.673   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.701  -4.667   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.803  -2.722   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.864  -1.280   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.126  -3.534   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.722  -4.166   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.889  -5.697   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.227 -11.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.941 -10.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.630  -5.580   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.623  -4.040   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.286  -3.276   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.956  -4.052   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.710  -3.002   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.511  -1.233   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.699  -1.627   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.699  -0.369   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.159  -3.481   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.657  -4.009   0.000  0.00  0.00           C+0
CONECT    1    2    8   12                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    1    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11    1   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10                                                       
CONECT   18    6                                                            
CONECT   19    5                                                            
CONECT   20    3   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22    2   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   22   27                                                       
CONECT   27   26                                                            
CONECT   28   21   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(+)-gamma-Schizandrin	ChEBI
(+)-Schizandrin b	ChEBI
gamma-Schisandrin	ChEBI
gamma-Schizandrin	ChEBI
Schisandrin b	ChEBI
Schizandrin b	ChEBI
Wuweizisu b	ChEBI
(+)-g-Schizandrin	Generator
(+)-Γ-schizandrin	Generator
g-Schisandrin	Generator
Γ-schisandrin	Generator
g-Schizandrin	Generator
Γ-schizandrin	Generator
(+--)-gamma-Schizandrin	MeSH
(-)-Gomisin N	MeSH

Chemical Formula

C₂₃H₂₈O₆

Average Mass

400.4710 Da

Monoisotopic Mass

400.18859 Da

IUPAC Name

(9R,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2,4,6,12,14(18)-hexaene

Traditional Name

(9R,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2,4,6,12,14(18)-hexaene

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1OC)C1=C(C[C@H](C)[C@H](C)C2)C=C2OCOC2=C1OC

InChI Identifier

InChI=1S/C23H28O6/c1-12-7-14-9-16(24-3)20(25-4)22(26-5)18(14)19-15(8-13(12)2)10-17-21(23(19)27-6)29-11-28-17/h9-10,12-13H,7-8,11H2,1-6H3/t12-,13+/m1/s1

InChI Key

RTZKSTLPRTWFEV-OLZOCXBDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 coccinea	LOTUS Database	35616633
Schisandra chinensis	Plant	KNApSAcK
Schisandra lancifolia	LOTUS Database	35616633
Schisandra propinqua	Plant	KNApSAcK

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
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tannin (CHEBI:4410 )
Lignans (C10555 )

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	4.37	ALOGPS
logP	4.64	ChemAxon
logS	-4.8	ALOGPS
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	4	ChemAxon
Refractivity	109.39 m³·mol⁻¹	ChemAxon
Polarizability	43.35 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

C00053774

Chemspider ID

139106

KEGG Compound ID

C10555

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

158103

PDB ID

Not Available

ChEBI ID

132471

Good Scents ID

Not Available

References

General References

Tan S, Zheng Z, Liu T, Yao X, Yu M, Ji Y: Schisandrin B Induced ROS-Mediated Autophagy and Th1/Th2 Imbalance via Selenoproteins in Hepa1-6 Cells. Front Immunol. 2022 Mar 28;13:857069. doi: 10.3389/fimmu.2022.857069. eCollection 2022. [PubMed:35419003 ]
Yan LS, Zhang SF, Luo G, Cheng BC, Zhang C, Wang YW, Qiu XY, Zhou XH, Wang QG, Song XL, Pan SY, Zhang Y: Schisandrin B mitigates hepatic steatosis and promotes fatty acid oxidation by inducing autophagy through AMPK/mTOR signaling pathway. Metabolism. 2022 Jun;131:155200. doi: 10.1016/j.metabol.2022.155200. Epub 2022 Apr 8. [PubMed:35405150 ]
Cao J, Liu Y, Zhou M, Dong S, Hou Y, Jia X, Lan X, Zhang Y, Guo J, Xiao G, Wang W: Screening of Botanical Drugs against SARS-CoV-2 Entry Reveals Novel Therapeutic Agents to Treat COVID-19. Viruses. 2022 Feb 8;14(2):353. doi: 10.3390/v14020353. [PubMed:35215943 ]
Lam HYP, Hung MY, Liang TR, Peng SY: An In-vivo Study into the Effects of Schisandrin B in the Liver, Spleen, Kidney, and Brain of Acute Thioacetamide-intoxicated Mice. Iran J Pharm Res. 2021 Fall;20(4):300-314. doi: 10.22037/ijpr.2021.115154.15225. [PubMed:35194448 ]
He L, Chen H, Qi Q, Wu N, Wang Y, Chen M, Feng Q, Dong B, Jin R, Jiang L: Schisandrin B suppresses gastric cancer cell growth and enhances the efficacy of chemotherapy drug 5-FU in vitro and in vivo. Eur J Pharmacol. 2022 Apr 5;920:174823. doi: 10.1016/j.ejphar.2022.174823. Epub 2022 Feb 11. [PubMed:35157912 ]

Showing NP-Card for Gomisin N (NP0054888)

MOL for NP0054888 (Gomisin N)

3D MOL for NP0054888 (Gomisin N)

3D SDF for NP0054888 (Gomisin N)

3D-SDF for NP0054888 (Gomisin N)

PDB for NP0054888 (Gomisin N)

3D PDB for NP0054888 (Gomisin N)

SMILES for NP0054888 (Gomisin N)

INCHI for NP0054888 (Gomisin N)

Structure for NP0054888 (Gomisin N)

3D Structure for NP0054888 (Gomisin N)