NP-MRD: Showing NP-Card for methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate (NP0281350)

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Record Information

Version

2.0

Created at

2022-09-09 07:38:24 UTC

Updated at

2022-09-09 07:38:24 UTC

NP-MRD ID

NP0281350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate

Description

Bruceanol B, also known as bruceanol-b, belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate is found in Brucea antidysenterica. Based on a literature review very few articles have been published on Bruceanol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092209382D          

 38 42  0  0  1  0            999 V2000
    3.7871    1.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5015    1.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160    1.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9305    1.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6450    1.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3594    1.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3594    0.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0739    1.9878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0739    2.8128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3856    3.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6462    2.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4537    4.0747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2006    4.4287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1344    5.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8171    5.7225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7919    6.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0652    6.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4935    6.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2202    6.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9218    7.0247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2453    5.7660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9721    5.3754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5438    5.3319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2658    4.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5494    4.5028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3229    4.2320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9496    4.7686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4706    3.4306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2277    3.1029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7653    2.9766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3539    2.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1475    1.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1488    2.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7374    2.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3522    2.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6848    2.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8921    3.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8504    3.3095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
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 16 18  2  0  0  0  0
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 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
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 13 37  1  0  0  0  0
 25 37  1  1  0  0  0
 38 37  1  6  0  0  0
  9 38  1  0  0  0  0
 30 38  1  0  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
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    2.2499    1.3973    2.6675 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    1.9459    1.9855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    1.6811    0.9723 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.0959    2.3469    0.1982 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.8650    1.3822   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9605   -0.9510   -0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1834   -0.1342   -3.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5143   -1.7645   -2.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3333   -0.9478   -1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090    0.4609   -0.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3548   -1.0231    0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
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 34 71  1  0
M  END


  Mrv1652309092209382D          

 38 42  0  0  1  0            999 V2000
    3.7871    1.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5015    1.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160    1.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9305    1.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6450    1.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3594    1.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3594    0.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0739    1.9878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0739    2.8128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3856    3.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6462    2.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4537    4.0747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2277    3.1029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1475    1.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1488    2.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7374    2.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3522    2.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6848    2.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8921    3.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8504    3.3095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 13 37  1  0  0  0  0
 25 37  1  1  0  0  0
 38 37  1  6  0  0  0
  9 38  1  0  0  0  0
 30 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)O[C@@H]1[C@@H]2C34CO[C@]2([C@@H](O)[C@H](O)[C@@H]3[C@@]2(C)[C@H](O)C(=O)C=C(C)[C@@H]2C[C@H]4OC1=O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O11/c1-5-6-7-8-16(29)38-18-20-26-11-36-27(20,24(34)35-4)22(32)17(30)19(26)25(3)13(10-15(26)37-23(18)33)12(2)9-14(28)21(25)31/h9,13,15,17-22,30-32H,5-8,10-11H2,1-4H3/t13-,15+,17+,18+,19+,20+,21+,22-,25-,26?,27+/m0/s1

> <INCHI_KEY>
NZDAVMOPAYYVCK-FIUJHEBUSA-N

> <FORMULA>
C27H36O11

> <MOLECULAR_WEIGHT>
536.574

> <EXACT_MASS>
536.225761979

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.76409837796974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-17-carboxylate

> <JCHEM_LOGP>
0.45641680599999923

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.147430175912778

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.530898017925761

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3240343992084993

> <JCHEM_POLAR_SURFACE_AREA>
165.89

> <JCHEM_REFRACTIVITY>
128.1148

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       7.069   3.711   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.403   2.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.737   3.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.070   2.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.404   3.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.738   2.941   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.738   1.401   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      15.071   3.711   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.071   5.251   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.787   6.072   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.406   5.389   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      13.914   7.606   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      15.308   8.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.184   9.826   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.459  10.682   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.412  12.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.055  12.950   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.721  13.031   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.078  12.302   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      20.387  13.113   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.125  10.763   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.481  10.034   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      17.815   9.953   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.163   9.208   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.826   8.405   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.269   7.900   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.439   8.901   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      19.545   6.404   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      20.958   5.792   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      18.229   5.556   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.327   4.477   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      18.942   2.986   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      20.811   4.889   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      21.910   3.810   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      17.457   4.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.212   5.279   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.599   7.298   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.521   6.178   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   38                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   37                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35   38                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   30   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   13   25   38                                             
CONECT   38   37    9   30                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Bruceanol-b	MeSH

Chemical Formula

C₂₇H₃₆O₁₁

Average Mass

536.5740 Da

Monoisotopic Mass

536.22576 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)O[C@@H]1[C@@H]2C34CO[C@]2([C@@H](O)[C@H](O)[C@@H]3[C@@]2(C)[C@H](O)C(=O)C=C(C)[C@@H]2C[C@H]4OC1=O)C(=O)OC

InChI Identifier

InChI=1S/C27H36O11/c1-5-6-7-8-16(29)38-18-20-26-11-36-27(20,24(34)35-4)22(32)17(30)19(26)25(3)13(10-15(26)37-23(18)33)12(2)9-14(28)21(25)31/h9,13,15,17-22,30-32H,5-8,10-11H2,1-4H3/t13-,15+,17+,18+,19+,20+,21+,22-,25-,26?,27+/m0/s1

InChI Key

NZDAVMOPAYYVCK-FIUJHEBUSA-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
Brucea antidysenterica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Triterpenoid
C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Furopyran
Cyclohexenone
Oxepane
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Beta-hydroxy acid
Fatty acyl
Pyran
Oxane
Hydroxy acid
Methyl ester
Tetrahydrofuran
Furan
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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

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

113358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bruceanol B

METLIN ID

Not Available

PubChem Compound

127804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate (NP0281350)

MOL for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D MOL for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D SDF for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D-SDF for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

PDB for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D PDB for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

SMILES for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

INCHI for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

Structure for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)

3D Structure for NP0281350 (methyl (2s,3r,6r,8s,12s,13s,14r,15r,16s,17r)-3-(hexanoyloxy)-12,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-17-carboxylate)