NP-MRD: Showing NP-Card for methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate (NP0223855)

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Record Information

Version

2.0

Created at

2022-09-06 02:04:17 UTC

Updated at

2022-09-06 02:04:17 UTC

NP-MRD ID

NP0223855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate

Description

Secomahoganin belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate is found in Swietenia macrophylla and Swietenia mahagoni. methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate was first documented in 2011 (PMID: 21742354). Based on a literature review a small amount of articles have been published on Secomahoganin (PMID: 30203950) (PMID: 32190758).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204042D          

 38 42  0  0  1  0            999 V2000
    0.8646   -3.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -2.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5303   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946   -0.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374   -1.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -2.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2481   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784   -3.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963   -4.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266   -5.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162   -4.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  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  1  0  0  0  0
 28 32  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 38 37  1  1  0  0  0
 36 38  1  0  0  0  0
 25 38  1  0  0  0  0
  5 38  1  0  0  0  0
M  END


  Mrv1652309062204042D          

 38 42  0  0  1  0            999 V2000
    0.8646   -3.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -2.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5303   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946   -0.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374   -1.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -2.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2481   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784   -3.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963   -4.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266   -5.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162   -4.6077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  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  1  0  0  0  0
 28 32  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 38 37  1  1  0  0  0
 36 38  1  0  0  0  0
 25 38  1  0  0  0  0
  5 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)[C@H](CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1)[C@@]1(C)C=CC(=O)C(C)(C)[C@@H]1COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-16(30)36-15-19-25(2,3)20(31)9-11-26(19,4)18-8-12-27(5)21(17-10-13-35-14-17)37-23(32)22-29(27,38-22)28(18,6)24(33)34-7/h9-11,13-14,18-19,21-22H,8,12,15H2,1-7H3/t18-,19+,21+,22-,26-,27+,28+,29-/m1/s1

> <INCHI_KEY>
PTLZHOLOQAFTMS-SCXLJDOTSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.72798176782578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6R)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

> <JCHEM_LOGP>
3.973383051

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.870044629673985

> <JCHEM_POLAR_SURFACE_AREA>
121.64000000000001

> <JCHEM_REFRACTIVITY>
133.61769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6R)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.614  -5.974   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.131  -5.707   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.174  -3.992   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.990  -4.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.527  -1.633   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.043  -1.365   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.033  -2.545   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.550  -2.278   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.506  -3.992   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.023  -4.260   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.506  -5.532   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.990  -4.260   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.463  -5.707   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.453  -6.887   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.926  -8.334   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.916  -9.513   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.590  -8.601   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.089   2.445   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.565   3.910   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.105   3.910   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.581   2.445   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   38                                             
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9   10   17                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    8   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    7   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   38                                             
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
CONECT   33   27   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36   38                                                       
CONECT   38   37   36   25    5                                             
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6R)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

Traditional Name

methyl (1R,3S,6R,7S,10R,11R)-10-[(1R,6R)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undecane-11-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)[C@H](CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1)[C@@]1(C)C=CC(=O)C(C)(C)[C@@H]1COC(C)=O

InChI Identifier

InChI=1S/C29H36O9/c1-16(30)36-15-19-25(2,3)20(31)9-11-26(19,4)18-8-12-27(5)21(17-10-13-35-14-17)37-23(32)22-29(27,38-22)28(18,6)24(33)34-7/h9-11,13-14,18-19,21-22H,8,12,15H2,1-7H3/t18-,19+,21+,22-,26-,27+,28+,29-/m1/s1

InChI Key

PTLZHOLOQAFTMS-SCXLJDOTSA-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
Swietenia macrophylla	LOTUS Database	35616633
Swietenia mahagoni	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
1,4-dioxepane
Delta valerolactone
Cyclohexenone
Dioxepane
Delta_valerolactone
Oxane
Heteroaromatic compound
Furan
Methyl ester
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.97	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	121.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	53.73 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

C00024095

Chemspider ID

10270594

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu JS, Zhu LL, Wang GK, Wang G: [Studies on Chemical Constituents from the Fruit of Swietenia macrophylla]. Zhong Yao Cai. 2016 Jul;39(7):1530-5. [PubMed:30203950 ]
Sukardiman, Ervina M: The recent use of Swietenia mahagoni (L.) Jacq. as antidiabetes type 2 phytomedicine: A systematic review. Heliyon. 2020 Mar 10;6(3):e03536. doi: 10.1016/j.heliyon.2020.e03536. eCollection 2020 Mar. [PubMed:32190758 ]
Nsiama TK, Okamura H, Hamada T, Morimoto Y, Doe M, Iwagawa T, Nakatani M: Rings D-seco and B,D-seco tetranortriterpenoids from root bark of Entandrophragma angolense. Phytochemistry. 2011 Oct;72(14-15):1854-8. doi: 10.1016/j.phytochem.2011.05.014. Epub 2011 Jul 19. [PubMed:21742354 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate (NP0223855)

MOL for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

3D MOL for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

3D SDF for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

3D-SDF for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

PDB for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

3D PDB for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

SMILES for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

INCHI for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

Structure for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)

3D Structure for NP0223855 (methyl (1r,3s,6s,7s,10r,11r)-10-[(1r,6r)-6-[(acetyloxy)methyl]-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undecane-11-carboxylate)