NP-MRD: Showing NP-Card for gambogeninol (NP0085832)

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Record Information

Version

2.0

Created at

2022-04-29 06:17:13 UTC

Updated at

2022-04-29 06:17:13 UTC

NP-MRD ID

NP0085832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gambogeninol

Description

gambogeninol is found in Garcinia hanburyi . Based on a literature review very few articles have been published on (1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-15-(4-hydroxy-3-methylbut-2-en-1-yl)-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-3,16-dioxapentacyclo[11.4.1.0²,¹¹.0²,¹⁵.0⁴,⁹]Octadeca-4,6,8,11-tetraene-10,14-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208172D          

 45 49  0  0  1  0            999 V2000
    6.9889    1.4060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0620   -0.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1079   -0.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292208172D          

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    9.1079   -0.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7524    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4887    0.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1791    0.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1332    1.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3969    1.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8236    1.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2501   -0.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6407   -1.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4329   -0.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9382   -1.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1096   -0.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828   -0.2748    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2812    0.2801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7515   -1.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9263   -1.5848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2336   -1.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990   -0.3281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9057    0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317    1.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3026    2.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5017    2.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8744    2.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6453    3.5607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619    0.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3581    0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583    1.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7248    1.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.1975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0691   -0.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4731   -1.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2508   -2.0515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1220    0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6284    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5662    1.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9307    2.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7526    2.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2255    1.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1016    3.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 21  2  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 25  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 19 35  1  0  0  0  0
 35 36  1  1  0  0  0
 22 36  1  0  0  0  0
 23 37  2  0  0  0  0
 17 38  2  0  0  0  0
 16 39  1  0  0  0  0
 20 39  1  0  0  0  0
 39 40  2  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC1=C(O)C(CC=C(C)C)=C2O[C@@]34[C@H]5C[C@@H](C=C3C(=O)C2=C1O)C(=O)[C@]4(CC=C(C)CO)OC5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C38H48O7/c1-21(2)10-9-11-23(5)13-15-26-31(40)27(14-12-22(3)4)34-30(32(26)41)33(42)28-18-25-19-29-36(7,8)45-37(35(25)43,38(28,29)44-34)17-16-24(6)20-39/h10,12-13,16,18,25,29,39-41H,9,11,14-15,17,19-20H2,1-8H3/b23-13+,24-16?/t25-,29+,37+,38-/m1/s1

> <INCHI_KEY>
JCMVTPCWKQJFSB-QQNADTFDSA-N

> <FORMULA>
C38H48O7

> <MOLECULAR_WEIGHT>
616.795

> <EXACT_MASS>
616.340003886

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
69.09622005836502

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-15-(4-hydroxy-3-methylbut-2-en-1-yl)-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-3,16-dioxapentacyclo[11.4.1.0^{2,11}.0^{2,15}.0^{4,9}]octadeca-4,6,8,11-tetraene-10,14-dione

> <ALOGPS_LOGP>
5.81

> <JCHEM_LOGP>
7.757717938666667

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.296013750871651

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.567785123706503

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797343114936053

> <JCHEM_POLAR_SURFACE_AREA>
113.28999999999999

> <JCHEM_REFRACTIVITY>
181.12640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-15-(4-hydroxy-3-methylbut-2-en-1-yl)-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-3,16-dioxapentacyclo[11.4.1.0^{2,11}.0^{2,15}.0^{4,9}]octadeca-4,6,8,11-tetraene-10,14-dione

> <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  O   UNK     0      13.046   2.625   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.032   1.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.612  -0.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.221  -0.234   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.541   0.629   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.916  -0.065   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.001  -1.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.204   0.778   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.579   0.083   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.868   0.926   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.782   2.464   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.408   3.158   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.071   3.307   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.667  -1.243   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.396  -2.657   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.141  -1.032   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.218  -2.291   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.671  -1.862   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.688  -0.513   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.992   0.523   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.003  -3.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.462  -2.958   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.169  -2.072   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.851  -0.612   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.424   1.362   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.593   2.578   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.165   4.057   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.670   4.426   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.232   5.167   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.804   6.647   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.476   0.225   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.402   1.451   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.722   2.067   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.086   3.154   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.526   0.369   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.729  -1.396   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.750  -2.905   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       9.802  -3.830   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.561   0.395   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.506   1.610   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.390   3.361   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.071   4.819   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.605   4.952   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.488   3.690   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      13.256   6.348   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   39                                                  
CONECT   17   16   18   38                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20   24   35                                             
CONECT   20   19   39                                                       
CONECT   21   18   22                                                       
CONECT   22   21   23   36                                                  
CONECT   23   22   24   37                                                  
CONECT   24   23   19   25   31                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   24   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   19   36                                                  
CONECT   36   35   22                                                       
CONECT   37   23                                                            
CONECT   38   17                                                            
CONECT   39   16   20   40                                                  
CONECT   40   39    2   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₄₈O₇

Average Mass

616.7950 Da

Monoisotopic Mass

616.34000 Da

IUPAC Name

(1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-6,8-dihydroxy-15-(4-hydroxy-3-methylbut-2-en-1-yl)-17,17-dimethyl-5-(3-methylbut-2-en-1-yl)-3,16-dioxapentacyclo[11.4.1.0^{2,11}.0^{2,15}.0^{4,9}]octadeca-4,6,8,11-tetraene-10,14-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC1=C(O)C(CC=C(C)C)=C2O[C@@]34[C@H]5C[C@@H](C=C3C(=O)C2=C1O)C(=O)[C@]4(CC=C(C)CO)OC5(C)C

InChI Identifier

InChI=1S/C38H48O7/c1-21(2)10-9-11-23(5)13-15-26-31(40)27(14-12-22(3)4)34-30(32(26)41)33(42)28-18-25-19-29-36(7,8)45-37(35(25)43,38(28,29)44-34)17-16-24(6)20-39/h10,12-13,16,18,25,29,39-41H,9,11,14-15,17,19-20H2,1-8H3/b23-13+,24-16?/t25-,29+,37+,38-/m1/s1

InChI Key

JCMVTPCWKQJFSB-QQNADTFDSA-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
Garcinia hanburyi	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	5.81	ALOGPS
logP	7.76	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	181.13 m³·mol⁻¹	ChemAxon
Polarizability	69.1 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	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

163184062

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for gambogeninol (NP0085832)

MOL for NP0085832 (gambogeninol)

3D MOL for NP0085832 (gambogeninol)

3D SDF for NP0085832 (gambogeninol)

3D-SDF for NP0085832 (gambogeninol)

PDB for NP0085832 (gambogeninol)

3D PDB for NP0085832 (gambogeninol)

SMILES for NP0085832 (gambogeninol)

INCHI for NP0085832 (gambogeninol)

Structure for NP0085832 (gambogeninol)

3D Structure for NP0085832 (gambogeninol)