NP-MRD: Showing NP-Card for (+)-Gnetuhainin C (NP0081081)

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Record Information

Version

1.0

Created at

2022-04-29 02:03:36 UTC

Updated at

2022-04-29 02:03:36 UTC

NP-MRD ID

NP0081081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Gnetuhainin C

Description

(1R,8R,9R,16R)-16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]Hexadeca-2(7),3,5,10(15),11,13-hexaene-4,6,12,14-tetrol belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. (+)-Gnetuhainin C is found in Gnetum hainanense. Based on a literature review very few articles have been published on (1R,8R,9R,16R)-16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]Hexadeca-2(7),3,5,10(15),11,13-hexaene-4,6,12,14-tetrol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292204032D          

 35 40  0  0  1  0            999 V2000
   -0.9103   -1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7300   -0.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6644   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -1.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3032   -1.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012   -2.0173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8262   -2.0139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5584   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1510   -0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4062   -0.2083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4298   -1.1634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2349   -1.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4883   -0.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -2.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -2.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931   -2.6037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7690   -1.8709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7534    0.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -0.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7297   -1.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272   -1.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932   -2.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932    0.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1872   -2.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -2.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3712   -3.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863   -4.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7253   -3.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -5.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1555    0.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214   -1.3114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  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  4  1  1  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
  8 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
  3 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END


  Mrv1652304292204032D          

 35 40  0  0  1  0            999 V2000
   -0.9103   -1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7300   -0.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6644   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -1.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3032   -1.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012   -2.0173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8262   -2.0139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5584   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1510   -0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4062   -0.2083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4298   -1.1634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2349   -1.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4883   -0.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -2.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -2.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931   -2.6037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7690   -1.8709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7534    0.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -0.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7297   -1.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272   -1.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932   -2.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932    0.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1872   -2.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -2.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3712   -3.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863   -4.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7253   -3.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -5.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1555    0.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214   -1.3114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  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  4  1  1  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
  8 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
  3 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@H]1[C@H]2[C@H]([C@@H](C3=C(O)C=C(O)C=C23)C2=C1C(O)=CC(O)=C2)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O7/c29-13-3-1-12(2-4-13)23-24-18(7-15(31)10-21(24)34)28-25-19(8-16(32)11-22(25)35)27(23)26(28)17-6-5-14(30)9-20(17)33/h1-11,23,26-35H/t23-,26-,27+,28-/m1/s1

> <INCHI_KEY>
MIPUQOUHHCMZTE-NNTQFHGGSA-N

> <FORMULA>
C28H22O7

> <MOLECULAR_WEIGHT>
470.477

> <EXACT_MASS>
470.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.76516467996859

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8R,9R,16R)-16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2(7),3,5,10,12,14-hexaene-4,6,12,14-tetrol

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
5.010589230333333

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.3946859993465

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.956470082252595

> <JCHEM_PKA_STRONGEST_BASIC>
-5.434899814510328

> <JCHEM_POLAR_SURFACE_AREA>
141.61

> <JCHEM_REFRACTIVITY>
129.9229

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8R,9R,16R)-16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2(7),3,5,10,12,14-hexaene-4,6,12,14-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.699  -1.983   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.363  -0.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.107  -0.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.240  -1.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.904  -2.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.566  -3.026   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.869  -3.766   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.409  -3.759   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.776  -2.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.015  -1.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.625  -0.389   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.669  -2.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.172  -2.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.215  -1.375   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.511  -1.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.177  -3.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.277  -3.903   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.632  -3.978   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.974  -4.860   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.902  -3.492   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.140   0.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.613  -0.447   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.962  -1.947   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.837  -2.999   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.454  -4.189   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.454   0.988   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.083  -5.144   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.619  -5.253   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.293  -6.637   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.431  -7.913   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.894  -7.805   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.221  -6.420   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.047  -9.406   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.290   1.561   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -3.213  -2.448   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   27                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
CONECT   21   10   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23    9   25                                                  
CONECT   25   24                                                            
CONECT   26   22                                                            
CONECT   27    8   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30                                                            
CONECT   34    3                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₂O₇

Average Mass

470.4770 Da

Monoisotopic Mass

470.13655 Da

IUPAC Name

(1R,8R,9R,16R)-16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2(7),3,5,10,12,14-hexaene-4,6,12,14-tetrol

Traditional Name

(1R,8R,9R,16R)-16-(2,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)tetracyclo[7.6.1.0^{2,7}.0^{10,15}]hexadeca-2(7),3,5,10,12,14-hexaene-4,6,12,14-tetrol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@H]1[C@H]2[C@H]([C@@H](C3=C(O)C=C(O)C=C23)C2=C1C(O)=CC(O)=C2)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C28H22O7/c29-13-3-1-12(2-4-13)23-24-18(7-15(31)10-21(24)34)28-25-19(8-16(32)11-22(25)35)27(23)26(28)17-6-5-14(30)9-20(17)33/h1-11,23,26-35H/t23-,26-,27+,28-/m1/s1

InChI Key

MIPUQOUHHCMZTE-NNTQFHGGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gnetum hainanense	Plant	KNApSAcK

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
Tetralin
Indane
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Polyol
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	3.37	ALOGPS
logP	5.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	141.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.92 m³·mol⁻¹	ChemAxon
Polarizability	48.77 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

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

162976803

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Gnetuhainin C (NP0081081)

MOL for NP0081081 ((+)-Gnetuhainin C)

3D MOL for NP0081081 ((+)-Gnetuhainin C)

3D SDF for NP0081081 ((+)-Gnetuhainin C)

3D-SDF for NP0081081 ((+)-Gnetuhainin C)

PDB for NP0081081 ((+)-Gnetuhainin C)

3D PDB for NP0081081 ((+)-Gnetuhainin C)

SMILES for NP0081081 ((+)-Gnetuhainin C)

INCHI for NP0081081 ((+)-Gnetuhainin C)

Structure for NP0081081 ((+)-Gnetuhainin C)

3D Structure for NP0081081 ((+)-Gnetuhainin C)