NP-MRD: Showing NP-Card for (1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol (NP0312480)

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Record Information

Version

2.0

Created at

2022-09-11 09:17:54 UTC

Updated at

2022-09-11 09:17:54 UTC

NP-MRD ID

NP0312480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

Description

Gnemonol M belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. (1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol is found in Gnetum gnemon. (1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol was first documented in 2014 (PMID: 24569530). Based on a literature review very few articles have been published on Gnemonol M.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112211172D          

 38 43  0  0  1  0            999 V2000
    1.6599   -0.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7848   -0.3111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254    0.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6648    0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772    1.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7166    1.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1450    0.7568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6622    1.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4495    1.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0567    1.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8767    2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309112211172D          

 38 43  0  0  1  0            999 V2000
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 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  2  0  0  0  0
 26 34  1  0  0  0  0
  5 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1[C@H]2[C@@H](C3=CC=C(O)C(OC)=C3)C3=C(O)C=C(O)C=C3[C@@H]1C1=C(O)C=C(O)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O8/c1-37-23-7-13(3-5-19(23)33)25-27-17(9-15(31)11-21(27)35)30-26(14-4-6-20(34)24(8-14)38-2)29(25)18-10-16(32)12-22(36)28(18)30/h3-12,25-26,29-36H,1-2H3/t25-,26?,29+,30-/m0/s1

> <INCHI_KEY>
JJWYSQXEIGBPJQ-PZHXIBQCSA-N

> <FORMULA>
C30H26O8

> <MOLECULAR_WEIGHT>
514.53

> <EXACT_MASS>
514.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
53.07434097992564

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,8S,9S)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

> <JCHEM_LOGP>
4.998812020666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.526266337139448

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.056699232192083

> <JCHEM_PKA_STRONGEST_BASIC>
-4.590806131005677

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
140.86839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,9S)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.098  -1.455   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.465  -0.581   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.914   1.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.108   1.201   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.877   2.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.071   3.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.871   1.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.836   2.612   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.306   2.152   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.439   3.194   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.985   2.796   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.103   4.697   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.634   5.158   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.507   6.758   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.500   4.115   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.116   4.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.725   4.128   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.601   5.180   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.127   4.733   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.367   6.213   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.623   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.902   2.180   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.359   1.076   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.376   2.628   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.331   1.419   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.656   0.035   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.518  -1.241   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.844  -2.626   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.307  -2.734   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.865  -4.292   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.446  -1.458   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.057  -2.613   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.052  -3.815   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.120  -0.073   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.526   3.804   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.023   3.468   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.562   1.999   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.157   1.948   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15    6   17                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24    7   26                                                  
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   26                                                       
CONECT   35    5   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₈

Average Mass

514.5300 Da

Monoisotopic Mass

514.16277 Da

IUPAC Name

(1R,8S,9S)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

Traditional Name

(1R,8S,9S)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1[C@H]2[C@@H](C3=CC=C(O)C(OC)=C3)C3=C(O)C=C(O)C=C3[C@@H]1C1=C(O)C=C(O)C=C21

InChI Identifier

InChI=1S/C30H26O8/c1-37-23-7-13(3-5-19(23)33)25-27-17(9-15(31)11-21(27)35)30-26(14-4-6-20(34)24(8-14)38-2)29(25)18-10-16(32)12-22(36)28(18)30/h3-12,25-26,29-36H,1-2H3/t25-,26?,29+,30-/m0/s1

InChI Key

JJWYSQXEIGBPJQ-PZHXIBQCSA-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
Gnetum gnemon	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Phenylnaphthalene
Dibenzocycloheptene
Methoxyphenol
Tetralin
Indane
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ether
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	5	ChemAxon
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-4.6	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	4	ChemAxon
Refractivity	140.87 m³·mol⁻¹	ChemAxon
Polarizability	53.07 Å³	ChemAxon
Number of Rings	6	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

C00037196

Chemspider ID

10189148

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21578121

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li W, Yang S, Lv T, Yang Y: Enzyme-promoted regioselective coupling oligomerization of isorhapontigenin towards the first synthesis of (+/-)-gnetulin. Org Biomol Chem. 2014 Apr 14;12(14):2273-9. doi: 10.1039/c3ob42456a. [PubMed:24569530 ]
LOTUS database [Link]

Showing NP-Card for (1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol (NP0312480)

MOL for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D MOL for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D SDF for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D-SDF for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

PDB for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D PDB for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

SMILES for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

INCHI for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

Structure for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D Structure for NP0312480 ((1r,8s,9s)-8,16-bis(4-hydroxy-3-methoxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)