NP-MRD: Showing NP-Card for meliatoosenin B (NP0035241)

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Record Information

Version

2.0

Created at

2021-06-20 18:44:31 UTC

Updated at

2021-06-30 00:06:07 UTC

NP-MRD ID

NP0035241

Secondary Accession Numbers

None

Natural Product Identification

Common Name

meliatoosenin B

Provided By

JEOL Database JEOL Logo

Description

Meliatoosenin B belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. meliatoosenin B is found in Dysoxylum grande and Melia toosendan. meliatoosenin B was first documented in 2010 (Zhang, Y., et al.). Based on a literature review very few articles have been published on Meliatoosenin B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120443D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202120443D          

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M  END
> <DATABASE_ID>
NP0035241

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@@]2([H])C(C(=O)C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]3(C(=C([H])C([H])([H])[C@@]3([H])[C@]3([H])C([H])([H])OC(=O)C3([H])[H])[C@]12C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O4/c1-23(2)19-13-21(28)26(5)17-7-6-16(15-12-22(29)30-14-15)24(17,3)10-8-18(26)25(19,4)11-9-20(23)27/h7,15-16,18-19,21,28H,6,8-14H2,1-5H3/t15-,16-,18+,19-,21+,24-,25+,26-/m0/s1

> <INCHI_KEY>
LZEIPUNOEUQFEG-VHESCTIXSA-N

> <FORMULA>
C26H38O4

> <MOLECULAR_WEIGHT>
414.586

> <EXACT_MASS>
414.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.448897120072075

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1R,2R,7R,9R,10R,14S,15S)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-14-yl]oxolan-2-one

> <ALOGPS_LOGP>
4.42

> <JCHEM_LOGP>
3.853405847333333

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.95498203948718

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3277955566063647

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
116.32779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1R,2R,7R,9R,10R,14S,15S)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-14-yl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
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  2  1  1  1
  2 10  1  0
  2  3  1  0
  8  7  1  0
  8  9  1  1
  8 10  1  0
 14 15  1  1
  4  5  2  0
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 12 13  1  0
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 26 28  1  0
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 26 16  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
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  6  4  1  0
 23 24  2  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
 10 44  1  1
 11 45  1  0
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 28 64  1  0
 28 65  1  0
 29 66  1  0
 29 67  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  1
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 27 62  1  0
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  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
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  3 36  1  0
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 15 49  1  0
 15 50  1  0
 15 51  1  0
 13 48  1  0
 21 57  1  0
 21 58  1  0
 25 59  1  0
 25 60  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.171  -2.923  -3.126  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.442  -1.557  -3.207  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.524  -0.469  -3.234  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.680  -1.516  -4.543  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.981  -2.236  -5.498  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.609  -0.464  -4.715  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.344  -0.413  -3.528  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.358  -0.270  -2.145  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.996   1.137  -2.066  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.406  -1.441  -2.035  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.028  -1.505  -0.618  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.964  -1.704   0.476  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.413  -3.012   0.259  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.153  -0.613   0.460  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.437   0.717   0.992  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.294  -0.965   1.427  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.184  -1.368   2.705  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.506  -1.398   3.398  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.357  -0.497   2.479  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.863  -0.719   2.675  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.331  -0.470   4.098  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.730  -0.209   3.993  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.005   0.239   2.734  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.102   0.623   2.364  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.761   0.225   1.898  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.753  -0.741   1.055  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.369  -1.988   0.387  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.856   0.493   0.151  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.971   0.426  -1.104  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.722  -0.493  -0.997  0.00  0.00           C+0
HETATM   31  H   UNK     0      -3.802  -3.095  -4.006  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.457  -3.752  -3.077  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.832  -2.985  -2.256  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.047  -0.392  -2.276  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.132   0.516  -3.493  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.279  -0.694  -3.998  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.096   0.498  -4.898  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.034  -0.704  -5.617  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.943  -1.334  -3.534  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.045   0.415  -3.688  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.916   1.152  -1.479  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.259   1.539  -3.047  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.323   1.879  -1.629  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.806  -2.361  -2.132  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.629  -0.616  -0.409  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.712  -2.358  -0.557  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.469  -1.730   1.449  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.248  -3.168   0.957  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.644   0.662   2.068  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.244   1.561   0.840  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.391   0.977   0.534  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.254  -1.569   3.222  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.884  -2.423   3.466  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.435  -0.974   4.404  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.141   0.545   2.767  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.134  -1.751   2.415  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.175  -1.345   4.737  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.851   0.398   4.564  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.980  -0.155   0.898  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.361   1.242   1.849  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.418  -1.816   0.123  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.331  -2.862   1.046  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.864  -2.276  -0.538  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.892   0.665  -0.160  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.570   1.390   0.717  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.593   0.058  -1.931  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.700   1.450  -1.377  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.114  -1.494  -1.224  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    4    1   10    3                                             
CONECT    3    2   34   35   36                                             
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    7    4   37   38                                             
CONECT    7    6    8   39   40                                             
CONECT    8   30    7    9   10                                             
CONECT    9    8   41   42   43                                             
CONECT   10   11    2    8   44                                             
CONECT   11   10   12   45   46                                             
CONECT   12   11   14   13   47                                             
CONECT   13   12   48                                                       
CONECT   14   12   30   15   16                                             
CONECT   15   14   49   50   51                                             
CONECT   16   17   14   26                                                  
CONECT   17   16   18   52                                                  
CONECT   18   17   19   53   54                                             
CONECT   19   18   26   20   55                                             
CONECT   20   19   21   25   56                                             
CONECT   21   20   22   57   58                                             
CONECT   22   21   23                                                       
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   20   59   60                                             
CONECT   26   19   27   28   16                                             
CONECT   27   26   61   62   63                                             
CONECT   28   26   29   64   65                                             
CONECT   29   30   28   66   67                                             
CONECT   30    8   14   29   68                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   15                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   17                                                            
CONECT   53   18                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   21                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
CONECT   65   28                                                            
CONECT   66   29                                                            
CONECT   67   29                                                            
CONECT   68   30                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

RDKit          3D

68 72  0  0  0  0  0  0  0  0999 V2000
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 25 60  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₄

Average Mass

414.5860 Da

Monoisotopic Mass

414.27701 Da

IUPAC Name

(4R)-4-[(1R,2R,7R,9R,10R,14S,15S)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-14-yl]oxolan-2-one

Traditional Name

(4R)-4-[(1R,2R,7R,9R,10R,14S,15S)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-14-yl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@@]2([H])C(C(=O)C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]3(C(=C([H])C([H])([H])[C@@]3([H])[C@]3([H])C([H])([H])OC(=O)C3([H])[H])[C@]12C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H38O4/c1-23(2)19-13-21(28)26(5)17-7-6-16(15-12-22(29)30-14-15)24(17,3)10-8-18(26)25(19,4)11-9-20(23)27/h7,15-16,18-19,21,28H,6,8-14H2,1-5H3/t15-,16-,18+,19-,21+,24-,25+,26-/m0/s1

InChI Key

LZEIPUNOEUQFEG-VHESCTIXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dysoxylum grande	LOTUS Database	35616633
Melia azedarach var. toosendan	JEOL database	Zhang, Y., et al, J. Nat. Prod. 73, 664 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Steroid lactone
3-oxosteroid
Hydroxysteroid
Oxosteroid
3-oxo-5-alpha-steroid
7-hydroxysteroid
Steroid
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.42	ALOGPS
logP	3.85	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	19.95	ChemAxon
pKa (Strongest Basic)	-0.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.33 m³·mol⁻¹	ChemAxon
Polarizability	47.45 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

101515882

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, Y., et al. (2010). Zhang, Y., et al, J. Nat. Prod. 73, 664 (2010). J. Nat. Prod..

Showing NP-Card for meliatoosenin B (NP0035241)

MOL for NP0035241 (meliatoosenin B)

3D MOL for NP0035241 (meliatoosenin B)

3D SDF for NP0035241 (meliatoosenin B)

3D-SDF for NP0035241 (meliatoosenin B)

PDB for NP0035241 (meliatoosenin B)

3D PDB for NP0035241 (meliatoosenin B)

SMILES for NP0035241 (meliatoosenin B)

INCHI for NP0035241 (meliatoosenin B)

Structure for NP0035241 (meliatoosenin B)

3D Structure for NP0035241 (meliatoosenin B)