NP-MRD: Showing NP-Card for (1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate (NP0160521)

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Record Information

Version

2.0

Created at

2022-09-02 18:29:47 UTC

Updated at

2022-09-02 18:29:47 UTC

NP-MRD ID

NP0160521

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

Description

(1R,2S,5R,7R,9R,10R,14S,15S)-9-hydroxy-14-[(2R,3S,5R)-5-[(1S)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-11-en-5-yl acetate 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. Based on a literature review very few articles have been published on (1R,2S,5R,7R,9R,10R,14S,15S)-9-hydroxy-14-[(2R,3S,5R)-5-[(1S)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-11-en-5-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220292D          

 41 45  0  0  1  0            999 V2000
   -0.5092   -3.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8690   -2.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061   -1.9944    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6864   -1.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350   -0.7121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0618    0.1125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6388    0.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    0.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003    1.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.8906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7494   -2.5921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.8418   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  1  0  0  0
  6  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
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
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 15 19  1  0  0  0  0
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 23 40  1  0  0  0  0
 40 41  1  6  0  0  0
M  END

     RDKit          3D

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 41 95  1  0
 41 96  1  0
 41 97  1  0
  6 47  1  1
  7 48  1  0
  9 49  1  0
  9 50  1  0
  9 51  1  0
 10 52  1  0
 10 53  1  0
 10 54  1  0
 12 55  1  0
 12 56  1  0
 12 57  1  0
M  END


  Mrv1652309022220292D          

 41 45  0  0  1  0            999 V2000
   -0.5092   -3.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8690   -2.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061   -1.9944    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6864   -1.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350   -0.7121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0618    0.1125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6388    0.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    0.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003    1.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.8906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    1.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -1.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3895   -1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9024   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7146   -4.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706   -4.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5903   -4.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  1  0  0  0
  6  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
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 18 40  1  0  0  0  0
 23 40  1  0  0  0  0
 40 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0160521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](OC(C)=O)C(C)(C)[C@@H]3C[C@@H](O)[C@@]21C)[C@H](O)C(C)(C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C34H56O7/c1-19(35)40-27-14-16-33(7)24-13-15-32(6)21(20-17-22(41-29(20)38-9)28(37)31(4,5)39-10)11-12-23(32)34(24,8)26(36)18-25(33)30(27,2)3/h12,20-22,24-29,36-37H,11,13-18H2,1-10H3/t20-,21-,22+,24+,25-,26+,27+,28-,29+,32-,33+,34-/m0/s1

> <INCHI_KEY>
SABPQJQTNUXWFJ-SPAWGUAVSA-N

> <FORMULA>
C34H56O7

> <MOLECULAR_WEIGHT>
576.815

> <EXACT_MASS>
576.402604143

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
66.435909890309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,7R,9R,10R,14S,15S)-9-hydroxy-14-[(2R,3S,5R)-5-[(1S)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl acetate

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.355959289666666

> <ALOGPS_LOGS>
-5.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.070572689839718

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3517456410911929

> <JCHEM_POLAR_SURFACE_AREA>
94.45

> <JCHEM_REFRACTIVITY>
158.11650000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,7R,9R,10R,14S,15S)-9-hydroxy-14-[(2R,3S,5R)-5-[(1S)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.950  -6.383   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.622  -4.997   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.758  -3.723   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.281  -2.274   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.065  -1.329   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.115   0.210   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.193   1.023   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.473   0.936   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.200  -0.422   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.747   2.294   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.831   1.662   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.881   3.202   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.209  -2.193   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.594  -3.453   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.885  -7.913   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.400  -8.184   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.892  -9.091   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.835  -9.184   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.312  -7.735   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   40                                                  
CONECT   19   18   15   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   40                                                  
CONECT   24   23   25   26   36                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   24   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   18   23   41                                             
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,5R,7R,9R,10R,14S,15S)-9-Hydroxy-14-[(2R,3S,5R)-5-[(1S)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0,.0,]heptadec-11-en-5-yl acetic acid	Generator

Chemical Formula

C₃₄H₅₆O₇

Average Mass

576.8150 Da

Monoisotopic Mass

576.40260 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](OC(C)=O)C(C)(C)[C@@H]3C[C@@H](O)[C@@]21C)[C@H](O)C(C)(C)OC

InChI Identifier

InChI=1S/C34H56O7/c1-19(35)40-27-14-16-33(7)24-13-15-32(6)21(20-17-22(41-29(20)38-9)28(37)31(4,5)39-10)11-12-23(32)34(24,8)26(36)18-25(33)30(27,2)3/h12,20-22,24-29,36-37H,11,13-18H2,1-10H3/t20-,21-,22+,24+,25-,26+,27+,28-,29+,32-,33+,34-/m0/s1

InChI Key

SABPQJQTNUXWFJ-SPAWGUAVSA-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

Not Available

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
Dihydroxy bile acid, alcohol, or derivatives
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
Hydroxysteroid
7-hydroxysteroid
Steroid
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Ether
Dialkyl ether
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
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
logP	4.62	ALOGPS
logP	4.36	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	158.12 m³·mol⁻¹	ChemAxon
Polarizability	66.44 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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Phenol Explorer Compound ID

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FoodDB 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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METLIN ID

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PubChem Compound

162951107

PDB ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate (NP0160521)

MOL for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D MOL for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D SDF for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D-SDF for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

PDB for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D PDB for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

SMILES for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

INCHI for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

Structure for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)

3D Structure for NP0160521 ((1s,3br,4r,5ar,7r,9as,9br,11as)-4-hydroxy-1-[(2r,3s,5r)-5-[(1s)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate)