NP-MRD: Showing NP-Card for Gomisin C (NP0137611)

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Record Information

Version

2.0

Created at

2022-05-30 16:57:42 UTC

Updated at

2022-05-30 16:57:42 UTC

NP-MRD ID

NP0137611

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gomisin C

Description

Gomisin C is found in Kadsura interior, Schisandra chinensis, Schisandra henryi, Schisandra propinqua, Schisandra rubriflora and Schisandra sphenanthera.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02271201342D          
 
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M  END

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  Mrv0541 02271201342D          
 
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  9  4  1  0  0  0  0
 10 28  1  0  0  0  0
  1  3  1  0  0  0  0
 20 29  1  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5  6  1  0  0  0  0
 30 34  1  0  0  0  0
  6  7  2  0  0  0  0
 14 35  1  0  0  0  0
  7  8  1  0  0  0  0
 20 36  1  0  0  0  0
 10 11  1  0  0  0  0
 35 37  1  0  0  0  0
 10 12  2  0  0  0  0
 36 38  1  0  0  0  0
 11 13  2  0  0  0  0
 22 39  1  1  0  0  0
 16  3  1  1  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(OC)=C2C(=C1)[C@H](OC(=O)C1=CC=CC=C1)[C@@](C)(O)[C@@H](C)CC1=C2C(OC)=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O9/c1-16-12-18-13-21-25(38-15-37-21)26(35-5)22(18)23-19(14-20(33-3)24(34-4)27(23)36-6)28(30(16,2)32)39-29(31)17-10-8-7-9-11-17/h7-11,13-14,16,28,32H,12,15H2,1-6H3/t16-,28-,30-/m0/s1

> <INCHI_KEY>
UFCGDBKFOKKVAC-DSASHONVSA-N

> <FORMULA>
C30H32O9

> <MOLECULAR_WEIGHT>
536.5697

> <EXACT_MASS>
536.204632622

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
56.27096396374404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,9S,10S)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl benzoate

> <ALOGPS_LOGP>
4.34

> <JCHEM_LOGP>
4.900408458333334

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.672217870328463

> <JCHEM_PKA_STRONGEST_BASIC>
-3.37957190351833

> <JCHEM_POLAR_SURFACE_AREA>
101.91000000000003

> <JCHEM_REFRACTIVITY>
142.1049

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8S,9S,10S)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      30.950 -27.694   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      32.284 -26.920   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      29.770 -26.766   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      30.950 -29.234   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.622 -29.996   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.622 -31.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.957 -32.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.292 -31.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.292 -29.996   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.055 -24.350   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.067 -22.863   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.677 -24.723   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.054 -21.864   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.214 -26.261   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      23.215 -24.011   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      28.612 -25.485   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.766 -20.357   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.529 -21.799   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      23.209 -23.016   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      25.311 -27.311   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.741 -24.800   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.459 -24.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.459 -22.786   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.901 -22.325   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      31.174 -24.498   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      30.692 -21.813   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.571 -22.284   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      27.072 -25.484   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.828 -27.047   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      25.143 -19.929   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      24.312 -18.641   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      22.825 -19.027   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      22.734 -20.561   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      24.235 -21.177   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      22.725 -26.651   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      24.863 -28.784   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      22.322 -28.137   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.362 -29.129   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      30.548 -25.753   0.000  0.00  0.00           C+0
CONECT    1    3    2    4                                                  
CONECT    2    1                                                            
CONECT    3    1   16                                                       
CONECT    4    9    1    5                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    9    7                                                       
CONECT    9    8    4                                                       
CONECT   10   28   11   12                                                  
CONECT   11   27   10   13                                                  
CONECT   12   15   10   14                                                  
CONECT   13   17   18   11                                                  
CONECT   14   20   35   12                                                  
CONECT   15   12   21                                                       
CONECT   16   28   22    3                                                  
CONECT   17   13   30                                                       
CONECT   18   13   23                                                       
CONECT   19   27   24                                                       
CONECT   20   14   29   36                                                  
CONECT   21   15                                                            
CONECT   22   16   25   23   39                                             
CONECT   23   18   26   22                                                  
CONECT   24   19                                                            
CONECT   25   22                                                            
CONECT   26   23                                                            
CONECT   27   34   19   11                                                  
CONECT   28   29   16   10                                                  
CONECT   29   28   20                                                       
CONECT   30   17   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   27   33   30                                                  
CONECT   35   14   37                                                       
CONECT   36   20   38                                                       
CONECT   37   35                                                            
CONECT   38   36                                                            
CONECT   39   22                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Gomisin C	Kegg
Schizandrer a	MeSH
Gomisin-g	MeSH
PC315 CPD	MeSH

Chemical Formula

C₃₀H₃₂O₉

Average Mass

536.5697 Da

Monoisotopic Mass

536.20463 Da

IUPAC Name

(8S,9S,10S)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl benzoate

Traditional Name

(8S,9S,10S)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2,4,6,13,18-hexaen-8-yl benzoate

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(OC)=C2C(=C1)[C@H](OC(=O)C1=CC=CC=C1)[C@@](C)(O)[C@@H](C)CC1=C2C(OC)=C2OCOC2=C1

InChI Identifier

InChI=1S/C30H32O9/c1-16-12-18-13-21-25(38-15-37-21)26(35-5)22(18)23-19(14-20(33-3)24(34-4)27(23)36-6)28(30(16,2)32)39-29(31)17-10-8-7-9-11-17/h7-11,13-14,16,28,32H,12,15H2,1-6H3/t16-,28-,30-/m0/s1

InChI Key

UFCGDBKFOKKVAC-DSASHONVSA-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 interior	LOTUS Database	35616633
Schisandra chinensis	LOTUS Database	35616633
Schisandra henryi	LOTUS Database	35616633
Schisandra propinqua	LOTUS Database	35616633
Schisandra rubriflora	LOTUS Database	35616633
Schisandra sphenanthera	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
Benzoate ester
Benzodioxole
Benzoic acid or derivatives
Anisole
Benzoyl
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Acetal
Ether
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tannin (CHEBI:9048 )
Lignans (C10881 )

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	4.34	ALOGPS
logP	4.9	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.67	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.91 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.1 m³·mol⁻¹	ChemAxon
Polarizability	56.27 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

FDB029994

KNApSAcK ID

C00002625

Chemspider ID

Not Available

KEGG Compound ID

C10881

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151529

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gomisin C (NP0137611)

MOL for NP0137611 (Gomisin C)

3D MOL for NP0137611 (Gomisin C)

3D SDF for NP0137611 (Gomisin C)

3D-SDF for NP0137611 (Gomisin C)

PDB for NP0137611 (Gomisin C)

3D PDB for NP0137611 (Gomisin C)

SMILES for NP0137611 (Gomisin C)

INCHI for NP0137611 (Gomisin C)

Structure for NP0137611 (Gomisin C)

3D Structure for NP0137611 (Gomisin C)