NP-MRD: Showing NP-Card for methyl angolensate (NP0042786)

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Record Information

Version

1.0

Created at

2021-06-21 00:21:56 UTC

Updated at

2021-06-30 00:18:04 UTC

NP-MRD ID

NP0042786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl angolensate

Provided By

JEOL Database JEOL Logo

Description

Methylangolensate 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. methyl angolensate is found in Carapa guianensis, Cipadessa baccifera , Ekebergia capensis, Entandrophragma angolense, Khaya anthotheca, Khaya grandifoliola, Khaya ivorensis, Khaya senegalensis, Lansium domesticum, Lansium domesticum Corr. , Melia azedarach, Neobeguea mahafalensis, Soymida febrifuga, Swietenia mahagoni , Xylocarpus granatum (Meliaceae) and Xylocarpus rumphii. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on methylangolensate (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454) (PMID: 26389451) (PMID: 26389436).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102213D          

 68 72  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306212102213D          

 68 72  0  0  0  0            999 V2000
    0.3270   -1.3905    3.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6219   -1.1153    2.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9435    0.3057    2.1231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4280    0.5348    2.5022 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4272   -0.5141    1.9897 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9705   -1.9831    2.2275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1378   -2.3370    3.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7929   -2.9607    1.3381 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.9923   -3.8271    2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3151   -3.4656    2.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4685   -2.4496    1.5333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2360   -2.1621    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887   -4.3093    1.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3649   -0.9323   -0.0437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2786   -0.9557   -1.5578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3332   -0.0839   -2.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0952   -0.5432   -3.0273 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5987    2.0440   -2.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1300    2.0733   -2.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6947   -2.6824    0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5890   -4.6169    3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2225   -3.8187    2.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2033   -1.3709    0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -3.8830    2.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674   -3.6666    1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -1.4506    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -1.9784   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010   -0.6189   -1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
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 11 10  2  0  0  0  0
 10  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3 37  1  1  0  0  0
 27 33  1  0  0  0  0
  2 18  1  0  0  0  0
  6  8  1  0  0  0  0
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 17 15  1  0  0  0  0
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 14  8  1  0  0  0  0
 27 24  1  0  0  0  0
 33 20  1  0  0  0  0
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  6  5  1  0  0  0  0
 22 23  2  0  0  0  0
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  5  4  1  0  0  0  0
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  6  7  1  1  0  0  0
 27 60  1  1  0  0  0
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 27 28  1  0  0  0  0
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 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 33  3  1  0  0  0  0
 31 32  1  0  0  0  0
  1  2  2  3  0  0  0
 20 19  1  0  0  0  0
 18 19  1  6  0  0  0
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 33 34  1  1  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  5 40  1  0  0  0  0
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 17 50  1  0  0  0  0
  8 45  1  6  0  0  0
  7 42  1  0  0  0  0
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  7 44  1  0  0  0  0
 13 48  1  0  0  0  0
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 25 54  1  0  0  0  0
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 34 67  1  0  0  0  0
 34 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1[C@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[C@]13O[C@@]1([H])C([H])([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C([H])([H])C(=O)OC([H])([H])[H])[C@@]21C([H])([H])[H])C1=C([H])OC([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O7/c1-15-17-7-9-25(4)23(16-8-10-32-14-16)33-22(30)13-27(15,25)34-20-12-19(28)24(2,3)18(26(17,20)5)11-21(29)31-6/h8,10,14,17-18,20,23H,1,7,9,11-13H2,2-6H3/t17-,18-,20-,23-,25-,26+,27-/m0/s1

> <INCHI_KEY>
YNMYHRYTRCKSMI-SQHTYAHXSA-N

> <FORMULA>
C27H34O7

> <MOLECULAR_WEIGHT>
470.562

> <EXACT_MASS>
470.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.575453083621554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1S,3S,7R,8R,9R,12S,13R)-13-(furan-3-yl)-6,6,8,12-tetramethyl-17-methylidene-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
3.818355261333334

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.07419990162942

> <JCHEM_PKA_STRONGEST_BASIC>
-2.869564081592046

> <JCHEM_POLAR_SURFACE_AREA>
92.04

> <JCHEM_REFRACTIVITY>
121.39609999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1S,3S,7R,8R,9R,12S,13R)-13-(furan-3-yl)-6,6,8,12-tetramethyl-17-methylidene-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
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   -0.9435    0.3057    2.1231 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.4272   -0.5141    1.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705   -1.9831    2.2275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1378   -2.3370    3.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7929   -2.9607    1.3381 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2731   -2.9687    1.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9923   -3.8271    2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3151   -3.4656    2.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4685   -2.4496    1.5333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2360   -2.1621    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887   -4.3093    1.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5832   -5.6169    0.7887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115   -3.5593    1.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892   -2.1141    1.7657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4764   -1.7326    0.3614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649   -0.9323   -0.0437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2786   -0.9557   -1.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332   -0.0839   -2.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5987    2.0440   -2.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4256   -1.9784   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8279    1.6872   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315    3.1574   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4136    1.1563    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0252    2.9491    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6315    0.3709    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    2.0203    1.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       0.327  -1.391   3.455  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.622  -1.115   2.544  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.944   0.306   2.123  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.428   0.535   2.502  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.427  -0.514   1.990  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.970  -1.983   2.228  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.138  -2.337   3.729  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.793  -2.961   1.338  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.273  -2.969   1.622  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.992  -3.827   2.506  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.315  -3.466   2.418  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.468  -2.450   1.533  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.236  -2.162   1.045  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.289  -4.309   1.435  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.974  -4.550   1.254  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.583  -5.617   0.789  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.012  -3.559   1.843  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.489  -2.114   1.766  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.476  -1.733   0.361  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.365  -0.932  -0.044  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.279  -0.956  -1.558  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.333  -0.084  -2.176  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.095  -0.543  -3.027  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.337   1.396  -1.774  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.599   2.044  -2.401  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.130   2.073  -2.443  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.395   1.488  -0.200  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.264   2.942   0.339  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.530   3.764   0.226  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.656   3.337   0.438  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.225   5.046  -0.114  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.365   5.899  -0.239  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.457   0.488   0.609  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.007   1.019   0.675  0.00  0.00           C+0
HETATM   35  H   UNK     0       0.580  -2.401   3.759  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.890  -0.596   3.938  0.00  0.00           H+0
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HETATM   40  H   UNK     0      -4.394  -0.331   2.476  0.00  0.00           H+0
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HETATM   45  H   UNK     0      -3.695  -2.682   0.279  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.589  -4.617   3.125  0.00  0.00           H+0
HETATM   47  H   UNK     0      -8.223  -3.819   2.888  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.203  -1.371   0.308  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.843  -3.883   2.876  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.067  -3.667   1.294  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.543  -1.451   0.298  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.426  -1.978  -1.926  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.701  -0.619  -1.910  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.517   1.637  -1.964  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.649   1.859  -3.481  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.607   3.130  -2.278  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.148   1.903  -3.528  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.828   1.687  -2.099  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.132   3.157  -2.294  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.414   1.156   0.021  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.025   2.949   1.409  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.441   3.465  -0.159  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.013   6.894  -0.526  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.890   5.978   0.718  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.036   5.530  -1.022  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.487   1.047  -0.303  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.632   0.371   1.301  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.068   2.020   1.110  0.00  0.00           H+0
CONECT    1    2   35   36                                                  
CONECT    2   18    1    3                                                  
CONECT    3    4   37   33    2                                             
CONECT    4    3    5   38   39                                             
CONECT    5    6    4   40   41                                             
CONECT    6    8    5    7   18                                             
CONECT    7    6   42   43   44                                             
CONECT    8    6   14    9   45                                             
CONECT    9   10    8   13                                                  
CONECT   10   11    9   46                                                  
CONECT   11   12   10   47                                                  
CONECT   12   13   11                                                       
CONECT   13   12    9   48                                                  
CONECT   14   15    8                                                       
CONECT   15   17   14   16                                                  
CONECT   16   15                                                            
CONECT   17   18   15   49   50                                             
CONECT   18    2   17    6   19                                             
CONECT   19   20   18                                                       
CONECT   20   33   21   19   51                                             
CONECT   21   20   22   52   53                                             
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   27   22   25   26                                             
CONECT   25   24   54   55   56                                             
CONECT   26   24   57   58   59                                             
CONECT   27   33   24   60   28                                             
CONECT   28   27   29   61   62                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   63   64   65                                             
CONECT   33   27   20    3   34                                             
CONECT   34   33   66   67   68                                             
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    7                                                            
CONECT   43    7                                                            
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   13                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   32                                                            
CONECT   64   32                                                            
CONECT   65   32                                                            
CONECT   66   34                                                            
CONECT   67   34                                                            
CONECT   68   34                                                            
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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M  END

View in JSmol

Synonyms

Value	Source
Methylangolensic acid	Generator
Angolensic acid methyl ester	MeSH
Methyl angolensate	MeSH

Chemical Formula

C₂₇H₃₄O₇

Average Mass

470.5620 Da

Monoisotopic Mass

470.23045 Da

IUPAC Name

methyl 2-[(1S,3S,7R,8R,9R,12S,13R)-13-(furan-3-yl)-6,6,8,12-tetramethyl-17-methylidene-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

Traditional Name

methyl [(1S,3S,7R,8R,9R,12S,13R)-13-(furan-3-yl)-6,6,8,12-tetramethyl-17-methylidene-5,15-dioxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1[C@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[C@]13O[C@@]1([H])C([H])([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C([H])([H])C(=O)OC([H])([H])[H])[C@@]21C([H])([H])[H])C1=C([H])OC([H])=C1[H]

InChI Identifier

InChI=1S/C27H34O7/c1-15-17-7-9-25(4)23(16-8-10-32-14-16)33-22(30)13-27(15,25)34-20-12-19(28)24(2,3)18(26(17,20)5)11-21(29)31-6/h8,10,14,17-18,20,23H,1,7,9,11-13H2,2-6H3/t17-,18-,20-,23-,25-,26+,27-/m0/s1

InChI Key

YNMYHRYTRCKSMI-SQHTYAHXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Carapa guianensis	LOTUS Database	35616633
Cipadessa baccifera	Plant	KNApSAcK
Ekebergia capensis	LOTUS Database	35616633
Entandrophragma angolense	LOTUS Database	35616633
Khaya anthotheca	Plant	KNApSAcK
Khaya grandifoliola	LOTUS Database	35616633
Khaya ivorensis	LOTUS Database	35616633
Khaya senegalensis	LOTUS Database	35616633
Lansium domesticum	LOTUS Database	35616633
Lansium domesticum Corr.	Plant	KNApSAcK
Melia azedarach	LOTUS Database	35616633
Neobeguea mahafalensis	LOTUS Database	35616633
Soymida febrifuga	LOTUS Database	35616633
Swietenia mahagoni	Plant	KNApSAcK
Xylocarpus granatum	JEOL database	Toume, K., et. al, Org. Lett. 15, 6106 (2013)
Xylocarpus rumphii	LOTUS Database	35616633

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
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Furan
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	4.05	ALOGPS
logP	3.82	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	18.07	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	92.04 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.4 m³·mol⁻¹	ChemAxon
Polarizability	49.58 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

10222053

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21596327

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
Authors unspecified: Cancer Prevention Overview (PDQ(R)): Health Professional Version. 2002. [PubMed:26389451 ]
Authors unspecified: Spirituality in Cancer Care (PDQ(R)): Health Professional Version. 2002. [PubMed:26389436 ]
Authors unspecified: Oral Cavity, Oropharyngeal, Hypopharyngeal, and Laryngeal Cancer Prevention (PDQ(R)): Health Professional Version. 2002. [PubMed:26389416 ]
Authors unspecified: Adjustment to Cancer: Anxiety and Distress (PDQ(R)): Health Professional Version. 2002. [PubMed:26389397 ]
Sakamoto A, Tanaka Y, Yamada T, Kikuchi T, Muraoka O, Ninomiya K, Morikawa T, Tanaka R: Andirolides W-Y from the flower oil of andiroba (Carapa guianensis, Meliaceae). Fitoterapia. 2015 Jan;100:81-7. doi: 10.1016/j.fitote.2014.09.003. Epub 2014 Sep 6. [PubMed:25200371 ]
Toume, K., et al. (2013). Toume, K., et. al, Org. Lett. 15, 6106 (2013). Org. Lett..

Showing NP-Card for methyl angolensate (NP0042786)

MOL for NP0042786 (methyl angolensate)

3D MOL for NP0042786 (methyl angolensate)

3D SDF for NP0042786 (methyl angolensate)

3D-SDF for NP0042786 (methyl angolensate)

PDB for NP0042786 (methyl angolensate)

3D PDB for NP0042786 (methyl angolensate)

SMILES for NP0042786 (methyl angolensate)

INCHI for NP0042786 (methyl angolensate)

Structure for NP0042786 (methyl angolensate)

3D Structure for NP0042786 (methyl angolensate)