NP-MRD: Showing NP-Card for (12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one (NP0169174)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 05:05:20 UTC

Updated at

2022-09-03 05:05:21 UTC

NP-MRD ID

NP0169174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one

Description

Schisantherin Q 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. (12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one is found in Kadsura angustifolia and Kadsura coccinea. Based on a literature review very few articles have been published on schisantherin Q.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032207052D          

 30 34  0  0  1  0            999 V2000
    1.6226    1.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3234    1.8447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219    2.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188    2.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886    4.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    4.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    3.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    3.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7969    4.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271    2.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    2.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692    2.1629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    1.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8016    1.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    2.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455    2.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.0571    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7338    5.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    5.6405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2756    6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    5.6405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7161    6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    5.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255    5.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    2.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6082    2.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    1.9033    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  2  0  0  0  0
  3  8  1  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  2  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -2.2710    0.5570   -2.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3148    0.0305   -1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199   -1.0066   -0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8234   -2.3429   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065   -3.3244   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174   -2.9668    0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -1.6564    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3078   -0.7131   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907    0.7432    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7343    1.6462   -0.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3845    2.9684   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8726    3.3544    0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8325    2.3948    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.0569    0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3929    0.0264    0.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4591   -0.5463    2.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089    3.0504    1.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288    4.4247    0.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4882    4.5751    0.4958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1289    1.5980   -0.7175 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7957    2.6360   -0.0350 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9072    0.3555   -0.5304 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8054   -0.6083   -1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -0.3098    0.8113 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2602   -0.7861    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -1.5107    0.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4404   -2.5416    1.3684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5286   -4.5331   -0.5325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097   -4.3307   -0.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9422   -2.9747   -1.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041    0.0539   -2.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3108    0.4130   -2.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506    1.6508   -2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -3.7159    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    3.7605   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5891   -0.3045    2.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6463   -1.6303    1.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4272   -0.1546    2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437    4.7765    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0596    4.9634    1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018    1.9125   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582    2.5407   -0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9969    0.7090   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7703   -1.1911   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7348   -0.0176   -2.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256   -1.3541   -1.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5566    0.4559    1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7524   -1.2292    0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215   -1.5333    2.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340    0.1034    1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4402   -4.4630    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2804   -5.0120   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 28  1  0
 28 29  1  0
 29 30  1  0
 30  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  7 26  1  0
 26 27  2  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
  9 14  1  0
  3  8  1  0
 12 13  1  0
 20 10  1  0
  4  5  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 11 35  1  0
  6 34  1  0
 29 51  1  0
 29 52  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 24 47  1  1
 25 48  1  0
 25 49  1  0
 25 50  1  0
 22 43  1  6
 23 44  1  0
 23 45  1  0
 23 46  1  0
 20 41  1  6
 21 42  1  0
M  END


  Mrv1652309032207052D          

 30 34  0  0  1  0            999 V2000
    1.6226    1.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3234    1.8447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219    2.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188    2.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886    4.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    4.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    3.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    3.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7969    4.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0104    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271    2.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    2.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692    2.1629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    1.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8016    1.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    2.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455    2.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.0571    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7338    5.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    5.6405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2756    6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084    5.6405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7161    6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    5.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255    5.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    2.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6082    2.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    1.9033    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  2  0  0  0  0
  3  8  1  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  2  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OCOC2=CC2=C1C1=C(C=C3OCOC3=C1OC)C(=O)[C@@H](C)[C@@H](C)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O8/c1-9-10(2)18(24)12-6-14-20(30-8-28-14)22(26-4)16(12)15-11(17(9)23)5-13-19(21(15)25-3)29-7-27-13/h5-6,9-10,17,23H,7-8H2,1-4H3/t9-,10+,17+/m1/s1

> <INCHI_KEY>
SEBKCRYGYKNELU-KEYDSSBGSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.41

> <EXACT_MASS>
414.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.461304229677644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
2.5366224719999995

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.579090807040213

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.196602733119558

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1458409009271566

> <JCHEM_POLAR_SURFACE_AREA>
92.68

> <JCHEM_REFRACTIVITY>
104.48470000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.029   1.875   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.470   3.443   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.028   5.323   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.515   4.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.604   6.014   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.205   7.501   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.718   7.900   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.629   6.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.089   6.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   7.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.488   7.501   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.886   6.014   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.797   4.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.690   5.323   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.622   4.037   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.356   2.268   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.496   3.553   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.017   3.794   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.258   5.315   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000   9.440   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.370  10.279   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.089  10.529   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.515  12.028   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.629  10.529   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.203  12.028   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.718   9.440   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.088  10.279   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.976   5.315   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.735   3.794   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.214   3.553   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12                                                       
CONECT   20   10   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    7   27                                                  
CONECT   27   26                                                            
CONECT   28    5   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    4                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₈

Average Mass

414.4100 Da

Monoisotopic Mass

414.13147 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C2OCOC2=CC2=C1C1=C(C=C3OCOC3=C1OC)C(=O)[C@@H](C)[C@@H](C)[C@@H]2O

InChI Identifier

InChI=1S/C22H22O8/c1-9-10(2)18(24)12-6-14-20(30-8-28-14)22(26-4)16(12)15-11(17(9)23)5-13-19(21(15)25-3)29-7-27-13/h5-6,9-10,17,23H,7-8H2,1-4H3/t9-,10+,17+/m1/s1

InChI Key

SEBKCRYGYKNELU-KEYDSSBGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Kadsura angustifolia	LOTUS Database	35616633
Kadsura coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Dibenzocyclooctane lignan
Benzodioxole
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Ketone
Secondary alcohol
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Organooxygen compound
Alcohol
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	1.94	ALOGPS
logP	2.54	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.2	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.48 m³·mol⁻¹	ChemAxon
Polarizability	41.46 Å³	ChemAxon
Number of Rings	5	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

C00040254

Chemspider ID

23340858

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44567620

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one (NP0169174)

MOL for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

3D MOL for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

3D SDF for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

3D-SDF for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

PDB for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

3D PDB for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

SMILES for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

INCHI for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

Structure for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)

3D Structure for NP0169174 ((12s,13r,14s)-14-hydroxy-3,22-dimethoxy-12,13-dimethyl-5,7,18,20-tetraoxapentacyclo[13.7.0.0²,¹⁰.0⁴,⁸.0¹⁷,²¹]docosa-1(15),2(10),3,8,16,21-hexaen-11-one)