NP-MRD: Showing NP-Card for (1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate (NP0171055)

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Record Information

Version

2.0

Created at

2022-09-03 07:24:35 UTC

Updated at

2022-09-03 07:24:35 UTC

NP-MRD ID

NP0171055

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate

Description

(1S,2R,7S,8R,9S,10R,14R,15S,16R,17S)-14-[(2R,5S)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-16,17-dihydroxy-8-methoxy-2,6,6,10,15-pentamethyl-3,13-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-4,11-dien-9-yl 3-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. (1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate is found in Azadirachta indica and Toona ciliata. Based on a literature review very few articles have been published on (1S,2R,7S,8R,9S,10R,14R,15S,16R,17S)-14-[(2R,5S)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-16,17-dihydroxy-8-methoxy-2,6,6,10,15-pentamethyl-3,13-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-4,11-dien-9-yl 3-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032209242D          

 42 46  0  0  1  0            999 V2000
    0.6857    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3736    3.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493    3.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9372    4.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 42 39  1  6  0  0  0
  3 42  1  0  0  0  0
 33 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309032209242D          

 42 46  0  0  1  0            999 V2000
    0.6857    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4978    2.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8417    2.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736    3.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493    3.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9372    4.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    4.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4023    1.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474   -2.0484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7742   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.7661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5814   -0.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7114   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0872   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -1.1393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 18 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 32 30  1  6  0  0  0
 12 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 42 39  1  6  0  0  0
  3 42  1  0  0  0  0
 33 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171055

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@@H](OC(=O)C=C(C)C)[C@]2(C)[C@H]([C@H](O)[C@H](O)[C@@]3(C)[C@@H](C(=O)C=C23)C2=C[C@@H](O)O[C@H]2O)[C@]2(C)[C@@H]1C(C)(C)C=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O10/c1-14(2)11-19(35)41-27-23(40-8)25-29(3,4)10-9-18(34)32(25,7)24-22(37)26(38)30(5)17(31(24,27)6)13-16(33)21(30)15-12-20(36)42-28(15)39/h9-13,20-28,36-39H,1-8H3/t20-,21+,22-,23+,24-,25-,26-,27+,28+,30+,31-,32+/m0/s1

> <INCHI_KEY>
VLJSCGXPWWMGGI-MUEBEZMGSA-N

> <FORMULA>
C32H42O10

> <MOLECULAR_WEIGHT>
586.678

> <EXACT_MASS>
586.277797552

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
60.976900758548574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,7S,8R,9S,10R,14R,15S,16R,17S)-14-[(2R,5S)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-16,17-dihydroxy-8-methoxy-2,6,6,10,15-pentamethyl-3,13-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,11-dien-9-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.247517061000001

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.87426953655364

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.790945989959594

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2938616164324035

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
153.57970000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7S,8R,9S,10R,14R,15S,16R,17S)-14-[(2R,5S)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-16,17-dihydroxy-8-methoxy-2,6,6,10,15-pentamethyl-3,13-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,11-dien-9-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.280   4.844   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.796   4.573   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.305   5.479   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.297   6.657   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.789   5.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.265   7.199   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.749   7.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.258   8.376   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.351   2.583   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.813   1.738   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.454  -2.959   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.728  -3.824   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.779  -5.363   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.944  -2.878   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.421  -1.430   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.285  -0.155   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.928  -2.940   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.896  -2.398   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.380  -2.127   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13   14   32                                             
CONECT   13   12                                                            
CONECT   14   12   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   18   14   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   12   33                                                  
CONECT   33   32   34   35   42                                             
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41   42                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   39    3   33                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,7S,8R,9S,10R,14R,15S,16R,17S)-14-[(2R,5S)-2,5-Dihydroxy-2,5-dihydrofuran-3-yl]-16,17-dihydroxy-8-methoxy-2,6,6,10,15-pentamethyl-3,13-dioxotetracyclo[8.7.0.0,.0,]heptadeca-4,11-dien-9-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₂H₄₂O₁₀

Average Mass

586.6780 Da

Monoisotopic Mass

586.27780 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@@H](OC(=O)C=C(C)C)[C@]2(C)[C@H]([C@H](O)[C@H](O)[C@@]3(C)[C@@H](C(=O)C=C23)C2=C[C@@H](O)O[C@H]2O)[C@]2(C)[C@@H]1C(C)(C)C=CC2=O

InChI Identifier

InChI=1S/C32H42O10/c1-14(2)11-19(35)41-27-23(40-8)25-29(3,4)10-9-18(34)32(25,7)24-22(37)26(38)30(5)17(31(24,27)6)13-16(33)21(30)15-12-20(36)42-28(15)39/h9-13,20-28,36-39H,1-8H3/t20-,21+,22-,23+,24-,25-,26-,27+,28+,30+,31-,32+/m0/s1

InChI Key

VLJSCGXPWWMGGI-MUEBEZMGSA-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
Azadirachta indica	LOTUS Database	35616633
Toona ciliata	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
Steroid ester
12-hydroxysteroid
Hydroxysteroid
16-oxosteroid
1-oxosteroid
Oxosteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Steroid
Fatty acid ester
Cyclohexenone
Fatty acyl
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
1,2-diol
Ketone
Hemiacetal
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Dialkyl ether
Ether
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

163047849

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate (NP0171055)

MOL for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

3D MOL for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

3D SDF for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

3D-SDF for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

PDB for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

3D PDB for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

SMILES for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

INCHI for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

Structure for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)

3D Structure for NP0171055 ((1r,3br,4s,5r,5as,9ar,9bs,10s,11r,11as)-1-[(2r,5s)-2,5-dihydroxy-2,5-dihydrofuran-3-yl]-10,11-dihydroxy-5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9-dioxo-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl 3-methylbut-2-enoate)