NP-MRD: Showing NP-Card for (+)-Gnetuhainin I (NP0075377)

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Record Information

Version

1.0

Created at

2022-04-28 20:39:24 UTC

Updated at

2022-04-28 20:39:24 UTC

NP-MRD ID

NP0075377

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Gnetuhainin I

Description

(-)-Gnetuhainin I belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. (+)-Gnetuhainin I is found in Gnetum hainanense and Gnetum hainanense C.Y.Cheng.. Based on a literature review very few articles have been published on (-)-Gnetuhainin I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222392D          

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M  END

     RDKit          3D

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  Mrv1652304282222392D          

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 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
  7 27  1  6  0  0  0
 27 28  1  0  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
 34 35  1  0  0  0  0
 31 36  1  0  0  0  0
 27 37  1  6  0  0  0
  3 38  1  0  0  0  0
  1 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075377

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@@H](O)[C@H]1[C@@H]([C@H](C2=C(O)C=C(O)C=C12)C1=CC=C(O)C(OC)=C1)C1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O9/c1-38-24-9-14(3-5-21(24)34)26-27(16-7-17(31)11-18(32)8-16)29(20-12-19(33)13-23(36)28(20)26)30(37)15-4-6-22(35)25(10-15)39-2/h3-13,26-27,29-37H,1-2H3/t26-,27-,29-,30-/m1/s1

> <INCHI_KEY>
WYHOIPCIJQFCKG-XQQPTAJKSA-N

> <FORMULA>
C30H28O9

> <MOLECULAR_WEIGHT>
532.545

> <EXACT_MASS>
532.173332482

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.99594317325574

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3S)-2-(3,5-dihydroxyphenyl)-1-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
4.398377430666666

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.43229707510654

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.958378507052398

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2222824592205432

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
143.72130000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S)-2-(3,5-dihydroxyphenyl)-1-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

> <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       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.698  -2.797   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.333  -1.652   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.839  -1.973   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.315  -3.437   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.222  -4.262   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.400   5.510   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.400   0.175   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.680   6.698   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.187   6.378   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.217   7.522   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.741   8.987   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.235   9.307   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.204   8.162   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.759  10.771   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.789  11.916   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.772  10.131   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.143   5.874   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       7.591   4.383   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    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   27                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19    8   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   21                                                            
CONECT   27    7   28   37                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   28                                                       
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   31                                                            
CONECT   37   27                                                            
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

C₃₀H₂₈O₉

Average Mass

532.5450 Da

Monoisotopic Mass

532.17333 Da

IUPAC Name

(1S,2R,3S)-2-(3,5-dihydroxyphenyl)-1-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

Traditional Name

(1S,2R,3S)-2-(3,5-dihydroxyphenyl)-1-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@@H](O)[C@H]1[C@@H]([C@H](C2=C(O)C=C(O)C=C12)C1=CC=C(O)C(OC)=C1)C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C30H28O9/c1-38-24-9-14(3-5-21(24)34)26-27(16-7-17(31)11-18(32)8-16)29(20-12-19(33)13-23(36)28(20)26)30(37)15-4-6-22(35)25(10-15)39-2/h3-13,26-27,29-37H,1-2H3/t26-,27-,29-,30-/m1/s1

InChI Key

WYHOIPCIJQFCKG-XQQPTAJKSA-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 hainanense	LOTUS Database	35616633
Gnetum hainanense C.Y.Cheng.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Indane
Anisole
Phenoxy compound
Phenol ether
Resorcinol
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Ether
Alcohol
Organooxygen compound
Aromatic alcohol
Hydrocarbon derivative
Organic oxygen 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	3.43	ALOGPS
logP	4.4	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	143.72 m³·mol⁻¹	ChemAxon
Polarizability	53 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	Yes	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

145709199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Gnetuhainin I (NP0075377)

MOL for NP0075377 ((+)-Gnetuhainin I)

3D MOL for NP0075377 ((+)-Gnetuhainin I)

3D SDF for NP0075377 ((+)-Gnetuhainin I)

3D-SDF for NP0075377 ((+)-Gnetuhainin I)

PDB for NP0075377 ((+)-Gnetuhainin I)

3D PDB for NP0075377 ((+)-Gnetuhainin I)

SMILES for NP0075377 ((+)-Gnetuhainin I)

INCHI for NP0075377 ((+)-Gnetuhainin I)

Structure for NP0075377 ((+)-Gnetuhainin I)

3D Structure for NP0075377 ((+)-Gnetuhainin I)