NP-MRD: Showing NP-Card for methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate (NP0286444)

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Record Information

Version

2.0

Created at

2022-09-09 15:01:41 UTC

Updated at

2022-09-09 15:01:41 UTC

NP-MRD ID

NP0286444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

Description

Methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadeca-12,16-diene-15-carboxylate 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 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate is found in Trichilia pallida. Methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadeca-12,16-diene-15-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241517482D          

 40 45  0  0  0  0            999 V2000
    3.0889    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449    3.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    3.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2063   -1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9193   -0.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019   -1.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3343   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1400    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6017    1.7357    0.0000 C   0  0  0  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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  2  0  0  0  0
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 14 15  2  0  0  0  0
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 16 18  1  0  0  0  0
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  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
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 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 31  1  0  0  0  0
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 34 35  2  0  0  0  0
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 34 38  1  0  0  0  0
 33 39  1  0  0  0  0
  6 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END

     RDKit          3D

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    2.0178    2.4198   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3107   -3.0939   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4040   -1.3450    1.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5759    2.5110   -1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9194    2.8889   -2.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1141   -3.6107    0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2612   -1.2884   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5832   -3.6808    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004241517482D          

 40 45  0  0  0  0            999 V2000
    3.0889    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2131    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3055    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2019   -1.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0540    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547   -0.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    2.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017    1.7357    0.0000 C   0  0  0  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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 38  1  0  0  0  0
 33 39  1  0  0  0  0
  6 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OC1C(O)C2C3(C)C=CC(=O)C(C)(C(=O)OC)C3=C(O)C(=O)C2(C)C23OC2CC(C2=COC=C2)C13C

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O10/c1-7-18(32)39-24-20(34)22-26(2)10-8-16(31)27(3,25(36)37-6)21(26)19(33)23(35)29(22,5)30-17(40-30)12-15(28(24,30)4)14-9-11-38-13-14/h8-11,13,15,17,20,22,24,33-34H,7,12H2,1-6H3

> <INCHI_KEY>
HKIUILMOGBEIDX-UHFFFAOYSA-N

> <FORMULA>
C30H34O10

> <MOLECULAR_WEIGHT>
554.592

> <EXACT_MASS>
554.215197295

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.553709761888314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.7031277300000003

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.855197682046342

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.01040263580911

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8581583336023932

> <JCHEM_POLAR_SURFACE_AREA>
152.87

> <JCHEM_REFRACTIVITY>
139.66599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.766   6.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.773   5.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257   5.657   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.734   7.106   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.264   4.480   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.788   3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.304   2.761   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.296   3.938   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.827   1.312   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.343   1.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.820   2.489   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.336   2.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.852   1.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.375   0.499   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.891   0.228   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.382  -0.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.852  -2.124   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.714  -1.452   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.049  -0.685   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.710  -2.992   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.042  -3.765   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.866  -0.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.873  -1.585   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.397  -3.033   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.357  -1.314   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.365  -2.491   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.834   0.135   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.254  -1.292   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.318   0.406   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.529  -1.120   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.102  -0.539   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.172   0.325   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.256   1.804   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.689   3.020   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.261   4.499   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.536   5.364   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.752   4.418   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.229   2.970   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.795   1.854   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.123   3.240   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                                                       
CONECT    6    5    7   39                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   27                                                  
CONECT   10    9   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   16   10   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    9   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   31   39                                             
CONECT   30   29   31                                                       
CONECT   31   30   29   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
CONECT   39   33    6   29   40                                             
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0,.0,.0,]octadeca-12,16-diene-15-carboxylic acid	Generator
Methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylic acid	Generator

Chemical Formula

C₃₀H₃₄O₁₀

Average Mass

554.5920 Da

Monoisotopic Mass

554.21520 Da

IUPAC Name

methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

Traditional Name

methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

CAS Registry Number

Not Available

SMILES

CCC(=O)OC1C(O)C2C3(C)C=CC(=O)C(C)(C(=O)OC)C3=C(O)C(=O)C2(C)C23OC2CC(C2=COC=C2)C13C

InChI Identifier

InChI=1S/C30H34O10/c1-7-18(32)39-24-20(34)22-26(2)10-8-16(31)27(3,25(36)37-6)21(26)19(33)23(35)29(22,5)30-17(40-30)12-15(28(24,30)4)14-9-11-38-13-14/h8-11,13,15,17,20,22,24,33-34H,7,12H2,1-6H3

InChI Key

HKIUILMOGBEIDX-UHFFFAOYSA-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
Trichilia pallida	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
17-furanylsteroid skeleton
Steroid ester
3-oxo-delta-1-steroid
1-hydroxysteroid
Hydroxysteroid
Oxosteroid
7-hydroxysteroid
7-oxosteroid
Delta-1-steroid
Steroid
Naphthopyran
Naphthalene
Cyclohexenone
Pyran
Oxane
Dicarboxylic acid or derivatives
Methyl ester
Cyclic alcohol
Heteroaromatic compound
Furan
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Enol
Oxirane
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
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	2.79	ALOGPS
logP	2.7	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	152.87 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.67 m³·mol⁻¹	ChemAxon
Polarizability	55.55 Å³	ChemAxon
Number of Rings	6	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

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

73809277

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate (NP0286444)

MOL for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D MOL for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D SDF for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D-SDF for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

PDB for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D PDB for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

SMILES for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

INCHI for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

Structure for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D Structure for NP0286444 (methyl 6-(furan-3-yl)-9,17-dihydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)