NP-MRD: Showing NP-Card for 9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate (NP0248933)

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Record Information

Version

2.0

Created at

2022-09-07 11:21:38 UTC

Updated at

2022-09-07 11:21:38 UTC

NP-MRD ID

NP0248933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate

Description

9-(Furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]Octadecan-17-yl 2-methylbut-2-enoate 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. 9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate is found in Swietenia mahagoni. 9-(Furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]Octadecan-17-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521042D          

 43 48  0  0  0  0            999 V2000
   -0.2104   -3.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6145   -3.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8377   -2.7104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5865   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2383   -2.0364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1130   -0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637    0.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803    0.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2481    2.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541    3.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8311    0.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048    0.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 19 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END

     RDKit          3D

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 20 66  1  0
M  END


  Mrv1533004161521042D          

 43 48  0  0  0  0            999 V2000
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    0.6145   -3.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1039   -1.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1130   -0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637    0.8666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803    0.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6672    1.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    2.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541    3.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921    1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311    0.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048    0.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7014    0.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5129    0.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2086   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7646   -1.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2098   -1.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0396   -1.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558   -1.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608   -2.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559   -0.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4809    0.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057    0.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7307    0.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056   -0.5914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2806   -1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6805   -2.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4994   -2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6567   -2.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9351   -3.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3318   -2.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688   -1.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8847   -2.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832   -0.5686    0.0000 O   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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 15 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 35 39  1  0  0  0  0
 24 40  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 19 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0248933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(O)C1C(C)(C)C(OC(=O)C(C)=CC)C2(O)C3OC33C(CCC4(C)C3CC(=O)OC4C3=COC=C3)C1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O11/c1-8-15(2)23(35)42-26-28(3,4)21(20(34)24(36)39-7)30(6)17-9-11-29(5)18(32(17)27(43-32)31(26,38)25(30)37)13-19(33)41-22(29)16-10-12-40-14-16/h8,10,12,14,17-18,20-22,26-27,34,38H,9,11,13H2,1-7H3

> <INCHI_KEY>
OWNYIZYKHUQFKG-UHFFFAOYSA-N

> <FORMULA>
C32H40O11

> <MOLECULAR_WEIGHT>
600.661

> <EXACT_MASS>
600.257062108

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
60.62485962284311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
3.398189097

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.440062283780382

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.089694666927347

> <JCHEM_PKA_STRONGEST_BASIC>
-2.870491642025657

> <JCHEM_POLAR_SURFACE_AREA>
162.10000000000002

> <JCHEM_REFRACTIVITY>
147.79639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -0.393  -6.468   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.147  -6.438   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.891  -5.090   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.430  -5.059   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.095  -3.771   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.445  -3.801   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.839  -2.423   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.962  -1.076   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.194  -2.093   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.211  -0.078   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.810   0.277   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.052   1.618   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.488   1.632   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.270   0.305   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.245   2.972   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.463   4.299   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.221   5.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.785   2.987   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.418   0.306   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.369   1.845   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.043   0.380   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.557   0.569   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.989  -0.921   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.161  -2.358   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.992  -3.703   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.541  -3.732   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.317  -2.397   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.073  -3.739   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.571  -1.050   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.364   0.270   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.904   0.243   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.697   1.563   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.650  -1.104   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.857  -2.424   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.604  -3.771   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.132  -3.959   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.426  -5.471   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      11.079  -6.217   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.953  -5.167   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.488  -2.446   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.518  -3.985   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.469  -1.100   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       5.009  -1.061   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   40                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19   11   20   21   42                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21   23                                                       
CONECT   23   22   21   24   29                                             
CONECT   24   23   25   40                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   34                                             
CONECT   28   27                                                            
CONECT   29   27   23   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   27   35                                                  
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   35                                                       
CONECT   40   24    7   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   19   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
9-(Furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0,.0,.0,]octadecan-17-yl 2-methylbut-2-enoic acid	Generator
9-(Furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₂H₄₀O₁₁

Average Mass

600.6610 Da

Monoisotopic Mass

600.25706 Da

IUPAC Name

9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate

Traditional Name

9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(O)C1C(C)(C)C(OC(=O)C(C)=CC)C2(O)C3OC33C(CCC4(C)C3CC(=O)OC4C3=COC=C3)C1(C)C2=O

InChI Identifier

InChI=1S/C32H40O11/c1-8-15(2)23(35)42-26-28(3,4)21(20(34)24(36)39-7)30(6)17-9-11-29(5)18(32(17)27(43-32)31(26,38)25(30)37)13-19(33)41-22(29)16-10-12-40-14-16/h8,10,12,14,17-18,20-22,26-27,34,38H,9,11,13H2,1-7H3

InChI Key

OWNYIZYKHUQFKG-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
Swietenia mahagoni	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
Mexicanolide
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Fatty acyl
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	3.21	ALOGPS
logP	3.4	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	162.1 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	147.8 m³·mol⁻¹	ChemAxon
Polarizability	60.62 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

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Phenol Explorer Compound ID

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KNApSAcK ID

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Chemspider ID

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KEGG Compound ID

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BioCyc ID

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BiGG ID

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METLIN ID

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PubChem Compound

73817601

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for 9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate (NP0248933)

MOL for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

3D MOL for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

3D SDF for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

3D-SDF for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

PDB for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

3D PDB for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

SMILES for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

INCHI for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

Structure for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)

3D Structure for NP0248933 (9-(furan-3-yl)-1-hydroxy-15-(1-hydroxy-2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]octadecan-17-yl 2-methylbut-2-enoate)