NP-MRD: Showing NP-Card for Gnetifolin C (NP0061293)

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Record Information

Version

2.0

Created at

2022-04-28 06:08:25 UTC

Updated at

2022-04-28 06:08:25 UTC

NP-MRD ID

NP0061293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gnetifolin C

Description

(8Z,16R,17R)-16-(3,5-dihydroxyphenyl)-8,17-dimethoxy-9-methyltetracyclo[16.4.0.0²,⁷.0¹⁰,¹⁵]Docosa-1(18),2(7),3,5,8,10(15),11,13,19,21-decaene-3,5,13,20-tetrol belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. Gnetifolin C is found in Gnetum parvifolium . Based on a literature review very few articles have been published on (8Z,16R,17R)-16-(3,5-dihydroxyphenyl)-8,17-dimethoxy-9-methyltetracyclo[16.4.0.0²,⁷.0¹⁰,¹⁵]Docosa-1(18),2(7),3,5,8,10(15),11,13,19,21-decaene-3,5,13,20-tetrol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208082D          

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M  END

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M  END


  Mrv1652304282208082D          

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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 16 26  1  0  0  0  0
 25 27  1  0  0  0  0
 15 28  1  6  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 32 34  1  0  0  0  0
 30 35  1  0  0  0  0
 14 36  1  1  0  0  0
 36 37  1  0  0  0  0
  3 38  1  0  0  0  0
  1 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H](C2=CC(O)=CC(O)=C2)C2=C(C=CC(O)=C2)\C(C)=C(OC)\C2=C(C(O)=CC(O)=C2)C2=C1C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C31H28O8/c1-15-22-6-4-17(32)11-24(22)28(16-8-19(34)10-20(35)9-16)31(39-3)25-12-18(33)5-7-23(25)29-26(30(15)38-2)13-21(36)14-27(29)37/h4-14,28,31-37H,1-3H3/b30-15-/t28-,31+/m1/s1

> <INCHI_KEY>
IJRNVYKGBFZZGA-BPXDBMNBSA-N

> <FORMULA>
C31H28O8

> <MOLECULAR_WEIGHT>
528.557

> <EXACT_MASS>
528.178417862

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.099333690443736

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8Z,16R,17R)-16-(3,5-dihydroxyphenyl)-8,17-dimethoxy-9-methyltetracyclo[16.4.0.0^{2,7}.0^{10,15}]docosa-1(18),2(7),3,5,8,10(15),11,13,19,21-decaene-3,5,13,20-tetrol

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
5.2718044903333325

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.613719420855078

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.058171578308242

> <JCHEM_PKA_STRONGEST_BASIC>
-4.074541544790096

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
148.57340000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8Z,16R,17R)-16-(3,5-dihydroxyphenyl)-8,17-dimethoxy-9-methyltetracyclo[16.4.0.0^{2,7}.0^{10,15}]docosa-1(18),2(7),3,5,8,10(15),11,13,19,21-decaene-3,5,13,20-tetrol

> <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      14.734  -0.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.238   1.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.230   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.717   1.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.213   0.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.221  -0.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.717  -2.140   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.205  -2.431   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.113  -4.172   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.709  -5.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.221  -4.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.726  -3.304   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.205  -6.506   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.609  -1.553   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.970  -2.146   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.677  -0.394   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.181   1.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.693   1.352   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.701   0.188   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.197  -1.267   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.685  -1.558   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.197   2.807   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.172   2.225   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.660   1.934   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.156   0.479   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.164  -0.685   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.644   0.188   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.181  -3.013   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.189  -4.178   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.685  -5.633   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.172  -5.924   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.164  -4.760   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668  -3.304   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.652  -5.051   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.693  -6.797   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.693  -2.722   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.701  -3.887   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      14.734   3.680   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      15.742  -1.558   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    8   15   36                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18    5   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   18                                                            
CONECT   23   17   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   16                                                       
CONECT   27   25                                                            
CONECT   28   15   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   28                                                       
CONECT   34   32                                                            
CONECT   35   30                                                            
CONECT   36   14   37                                                       
CONECT   37   36                                                            
CONECT   38    3                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₈O₈

Average Mass

528.5570 Da

Monoisotopic Mass

528.17842 Da

IUPAC Name

(8Z,16R,17R)-16-(3,5-dihydroxyphenyl)-8,17-dimethoxy-9-methyltetracyclo[16.4.0.0^{2,7}.0^{10,15}]docosa-1(18),2(7),3,5,8,10(15),11,13,19,21-decaene-3,5,13,20-tetrol

Traditional Name

(8Z,16R,17R)-16-(3,5-dihydroxyphenyl)-8,17-dimethoxy-9-methyltetracyclo[16.4.0.0^{2,7}.0^{10,15}]docosa-1(18),2(7),3,5,8,10(15),11,13,19,21-decaene-3,5,13,20-tetrol

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H](C2=CC(O)=CC(O)=C2)C2=C(C=CC(O)=C2)\C(C)=C(OC)\C2=C(C(O)=CC(O)=C2)C2=C1C=C(O)C=C2

InChI Identifier

InChI=1S/C31H28O8/c1-15-22-6-4-17(32)11-24(22)28(16-8-19(34)10-20(35)9-16)31(39-3)25-12-18(33)5-7-23(25)29-26(30(15)38-2)13-21(36)14-27(29)37/h4-14,28,31-37H,1-3H3/b30-15-/t28-,31+/m1/s1

InChI Key

IJRNVYKGBFZZGA-BPXDBMNBSA-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
Gnetum parvifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.15	ALOGPS
logP	5.27	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	148.57 m³·mol⁻¹	ChemAxon
Polarizability	54.1 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163104436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gnetifolin C (NP0061293)

MOL for NP0061293 (Gnetifolin C)

3D MOL for NP0061293 (Gnetifolin C)

3D SDF for NP0061293 (Gnetifolin C)

3D-SDF for NP0061293 (Gnetifolin C)

PDB for NP0061293 (Gnetifolin C)

3D PDB for NP0061293 (Gnetifolin C)

SMILES for NP0061293 (Gnetifolin C)

INCHI for NP0061293 (Gnetifolin C)

Structure for NP0061293 (Gnetifolin C)

3D Structure for NP0061293 (Gnetifolin C)