NP-MRD: Showing NP-Card for Linalool (8-hydroxydihydro-) (NP0050129)

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Record Information

Version

2.0

Created at

2022-03-17 21:23:44 UTC

Updated at

2022-03-17 21:23:44 UTC

NP-MRD ID

NP0050129

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Linalool (8-hydroxydihydro-)

Description

Limonin 17-beta-D-glucoside, also known as beta-D-glucosyl-limonin, 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. Linalool (8-hydroxydihydro-) is found in Citrus aurantium, Citrus iyo, Citrus junos, Citrus macrophylla, Citrus reticulata and Citrus sinensis. Limonin 17-beta-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304022019473D          

 46 52  0  0  0  0            999 V2000
   -5.3466   -0.5555    3.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5198    0.5625    1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -0.0044    1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2388    2.2954   -1.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966   -0.5737   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6009    0.2351   -3.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -0.8652   -0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158    1.0404   -4.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8037    1.7752    1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4249   -2.5665   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8611   -0.6400   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080    1.9634   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4432    0.1758   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0445    0.8253   -2.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8262   -0.8325   -0.8158 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1715   -0.0324   -0.0598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0175    0.3302    1.3747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3039    1.9344    1.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0359   -1.6564    0.4056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6068   -1.9435   -1.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3345   -1.7751    0.2246 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2480   -2.1704    1.2065 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9232   -2.3928    0.4372 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9466    0.4292   -0.7000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1786    2.9281    0.4704 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1859    3.3811    1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6629   -1.1099   -0.2597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2981   -0.2812    1.7034 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6501    0.3766   -0.0190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6988    1.3844    0.0806 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6254   -0.2603    0.0066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2012    1.5674    0.0800 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0972   -0.2730   -1.3783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7331    2.4625    2.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5302   -2.5621   -1.9281 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2974   -1.0684    0.9815 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5994   -3.2753    1.9401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845   -2.8002    1.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2682    2.8685    1.6840 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    4.6034    2.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6782    2.0697   -3.8255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6563   -0.5647   -1.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6147   -1.1968   -1.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285   -0.9379   -0.7994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2737   -1.4926    1.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    2.5723   -0.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  1  0  0  0  0
  2 28  1  0  0  0  0
 29  3  1  1  0  0  0
 30  4  1  6  0  0  0
  5  7  1  0  0  0  0
 16  5  1  6  0  0  0
  6  8  2  0  0  0  0
  6 14  1  0  0  0  0
  7 29  1  0  0  0  0
  8 41  1  0  0  0  0
 17  9  1  6  0  0  0
  9 18  1  0  0  0  0
 19 10  1  6  0  0  0
 10 20  1  0  0  0  0
 15 11  1  6  0  0  0
 11 33  1  0  0  0  0
 12 14  2  0  0  0  0
 12 41  1  0  0  0  0
 31 13  1  6  0  0  0
 13 42  1  0  0  0  0
 14 24  1  0  0  0  0
 15 21  1  0  0  0  0
 15 43  1  0  0  0  0
 16 30  1  0  0  0  0
 16 31  1  0  0  0  0
 17 28  1  0  0  0  0
 17 31  1  0  0  0  0
 18 30  1  0  0  0  0
 18 34  2  0  0  0  0
 19 31  1  0  0  0  0
 19 45  1  0  0  0  0
 20 35  2  0  0  0  0
 20 42  1  0  0  0  0
 21 22  1  0  0  0  0
 21 36  1  1  0  0  0
 22 23  1  0  0  0  0
 22 37  1  6  0  0  0
 23 27  1  0  0  0  0
 23 38  1  1  0  0  0
 24 29  1  0  0  0  0
 24 44  1  6  0  0  0
 25 26  1  1  0  0  0
 25 32  1  0  0  0  0
 25 46  1  0  0  0  0
 26 39  2  0  0  0  0
 26 40  1  0  0  0  0
 27 43  1  0  0  0  0
 27 44  1  6  0  0  0
 28 45  1  0  0  0  0
 29 32  1  0  0  0  0
 30 32  1  0  0  0  0
 32 46  1  6  0  0  0
M  END


  Mrv1652304022019473D          

 46 52  0  0  0  0            999 V2000
   -5.3466   -0.5555    3.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5198    0.5625    1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -0.0044    1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2388    2.2954   -1.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966   -0.5737   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6009    0.2351   -3.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -0.8652   -0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158    1.0404   -4.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8037    1.7752    1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4249   -2.5665   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8611   -0.6400   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080    1.9634   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4432    0.1758   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0445    0.8253   -2.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8262   -0.8325   -0.8158 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1715   -0.0324   -0.0598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0175    0.3302    1.3747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3039    1.9344    1.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0359   -1.6564    0.4056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6068   -1.9435   -1.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3345   -1.7751    0.2246 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2480   -2.1704    1.2065 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9232   -2.3928    0.4372 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9466    0.4292   -0.7000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1786    2.9281    0.4704 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1859    3.3811    1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6629   -1.1099   -0.2597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2981   -0.2812    1.7034 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6501    0.3766   -0.0190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6988    1.3844    0.0806 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6254   -0.2603    0.0066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2012    1.5674    0.0800 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0972   -0.2730   -1.3783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7331    2.4625    2.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5302   -2.5621   -1.9281 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2974   -1.0684    0.9815 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5994   -3.2753    1.9401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845   -2.8002    1.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2682    2.8685    1.6840 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    4.6034    2.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6782    2.0697   -3.8255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6563   -0.5647   -1.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6147   -1.1968   -1.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285   -0.9379   -0.7994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2737   -1.4926    1.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    2.5723   -0.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  1  0  0  0  0
  2 28  1  0  0  0  0
 29  3  1  1  0  0  0
 30  4  1  6  0  0  0
  5  7  1  0  0  0  0
 16  5  1  6  0  0  0
  6  8  2  0  0  0  0
  6 14  1  0  0  0  0
  7 29  1  0  0  0  0
  8 41  1  0  0  0  0
 17  9  1  6  0  0  0
  9 18  1  0  0  0  0
 19 10  1  6  0  0  0
 10 20  1  0  0  0  0
 15 11  1  6  0  0  0
 11 33  1  0  0  0  0
 12 14  2  0  0  0  0
 12 41  1  0  0  0  0
 31 13  1  6  0  0  0
 13 42  1  0  0  0  0
 14 24  1  0  0  0  0
 15 21  1  0  0  0  0
 15 43  1  0  0  0  0
 16 30  1  0  0  0  0
 16 31  1  0  0  0  0
 17 28  1  0  0  0  0
 17 31  1  0  0  0  0
 18 30  1  0  0  0  0
 18 34  2  0  0  0  0
 19 31  1  0  0  0  0
 19 45  1  0  0  0  0
 20 35  2  0  0  0  0
 20 42  1  0  0  0  0
 21 22  1  0  0  0  0
 21 36  1  1  0  0  0
 22 23  1  0  0  0  0
 22 37  1  6  0  0  0
 23 27  1  0  0  0  0
 23 38  1  1  0  0  0
 24 29  1  0  0  0  0
 24 44  1  6  0  0  0
 25 26  1  1  0  0  0
 25 32  1  0  0  0  0
 25 46  1  0  0  0  0
 26 39  2  0  0  0  0
 26 40  1  0  0  0  0
 27 43  1  0  0  0  0
 27 44  1  6  0  0  0
 28 45  1  0  0  0  0
 29 32  1  0  0  0  0
 30 32  1  0  0  0  0
 32 46  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@](C)([C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=COC=C2)[C@@]11O[C@@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O14/c1-28(2)17-9-18(34)30(4)16(31(17)13-42-20(35)10-19(31)45-28)5-7-29(3,32(30)25(46-32)26(39)40)24(14-6-8-41-12-14)44-27-23(38)22(37)21(36)15(11-33)43-27/h6,8,12,15-17,19,21-25,27,33,36-38H,5,7,9-11,13H2,1-4H3,(H,39,40)/t15-,16+,17+,19+,21-,22+,23-,24+,25-,27+,29+,30+,31-,32-/m1/s1

> <INCHI_KEY>
FYIKIBQJAJRKQM-WNCNYDOCSA-N

> <FORMULA>
C32H42O14

> <MOLECULAR_WEIGHT>
650.674

> <EXACT_MASS>
650.257456032

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
64.2595235636455

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid

> <ALOGPS_LOGP>
1.07

> <JCHEM_LOGP>
0.021884370666664238

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210048392067828

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.967095090298173

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888674246588524

> <JCHEM_POLAR_SURFACE_AREA>
214.94999999999996

> <JCHEM_REFRACTIVITY>
150.62470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      -5.347  -0.556   3.204  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.520   0.563   1.421  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.974  -0.004   1.448  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.239   2.295  -1.012  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.397  -0.574  -1.195  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.601   0.235  -3.252  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.028  -0.865  -0.618  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.016   1.040  -4.292  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.804   1.775   1.478  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.425  -2.567  -0.729  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.861  -0.640  -1.903  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.708   1.963  -2.540  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.443   0.176  -1.125  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.045   0.825  -2.118  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.826  -0.833  -0.816  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.172  -0.032  -0.060  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.018   0.330   1.375  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.304   1.934   1.357  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.036  -1.656   0.406  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.607  -1.944  -1.368  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.335  -1.775   0.225  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.248  -2.170   1.206  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.923  -2.393   0.437  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.947   0.429  -0.700  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.179   2.928   0.470  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.186   3.381   1.389  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.663  -1.110  -0.260  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.298  -0.281   1.703  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.650   0.377  -0.019  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.699   1.384   0.081  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.625  -0.260   0.007  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.201   1.567   0.080  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.097  -0.273  -1.378  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.733   2.462   2.247  0.00  0.00           O+0
HETATM   35  O   UNK     0      -6.530  -2.562  -1.928  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.297  -1.068   0.982  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.599  -3.275   1.940  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.985  -2.800   1.333  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.268   2.869   1.684  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.950   4.603   2.094  0.00  0.00           O+0
HETATM   41  O   UNK     0       2.678   2.070  -3.825  0.00  0.00           O+0
HETATM   42  O   UNK     0      -5.656  -0.565  -1.320  0.00  0.00           O+0
HETATM   43  O   UNK     0       4.615  -1.197  -1.386  0.00  0.00           O+0
HETATM   44  O   UNK     0       2.429  -0.938  -0.799  0.00  0.00           O+0
HETATM   45  O   UNK     0      -5.274  -1.493   1.088  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.358   2.572  -0.838  0.00  0.00           O+0
CONECT    1   28                                                            
CONECT    2   28                                                            
CONECT    3   29                                                            
CONECT    4   30                                                            
CONECT    5    7   16                                                       
CONECT    6    8   14                                                       
CONECT    7    5   29                                                       
CONECT    8    6   41                                                       
CONECT    9   17   18                                                       
CONECT   10   19   20                                                       
CONECT   11   15   33                                                       
CONECT   12   14   41                                                       
CONECT   13   31   42                                                       
CONECT   14    6   12   24                                                  
CONECT   15   11   21   43                                                  
CONECT   16    5   30   31                                                  
CONECT   17    9   28   31                                                  
CONECT   18    9   30   34                                                  
CONECT   19   10   31   45                                                  
CONECT   20   10   35   42                                                  
CONECT   21   15   22   36                                                  
CONECT   22   21   23   37                                                  
CONECT   23   22   27   38                                                  
CONECT   24   14   29   44                                                  
CONECT   25   26   32   46                                                  
CONECT   26   25   39   40                                                  
CONECT   27   23   43   44                                                  
CONECT   28    1    2   17   45                                             
CONECT   29    3    7   24   32                                             
CONECT   30    4   16   18   32                                             
CONECT   31   13   16   17   19                                             
CONECT   32   25   29   30   46                                             
CONECT   33   11                                                            
CONECT   34   18                                                            
CONECT   35   20                                                            
CONECT   36   21                                                            
CONECT   37   22                                                            
CONECT   38   23                                                            
CONECT   39   26                                                            
CONECT   40   26                                                            
CONECT   41    8   12                                                       
CONECT   42   13   20                                                       
CONECT   43   15   27                                                       
CONECT   44   24   27                                                       
CONECT   45   19   28                                                       
CONECT   46   25   32                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

View in JSmol

Synonyms

Value	Source
beta-D-Glucosyl-limonin	ChEBI
Glucosyl-limonin	ChEBI
Limonin 17-beta-D-glucopyranoside	ChEBI
b-D-Glucosyl-limonin	Generator
Β-D-glucosyl-limonin	Generator
Limonin 17-b-D-glucopyranoside	Generator
Limonin 17-β-D-glucopyranoside	Generator
Limonin 17-b-D-glucoside	Generator
Limonin 17-β-D-glucoside	Generator
Limonin 17-beta-D-glucoside	KEGG

Chemical Formula

C₃₂H₄₂O₁₄

Average Mass

650.6740 Da

Monoisotopic Mass

650.25746 Da

IUPAC Name

(1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid

Traditional Name

(1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@](C)([C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=COC=C2)[C@@]11O[C@@H]1C(O)=O

InChI Identifier

InChI=1S/C32H42O14/c1-28(2)17-9-18(34)30(4)16(31(17)13-42-20(35)10-19(31)45-28)5-7-29(3,32(30)25(46-32)26(39)40)24(14-6-8-41-12-14)44-27-23(38)22(37)21(36)15(11-33)43-27/h6,8,12,15-17,19,21-25,27,33,36-38H,5,7,9-11,13H2,1-4H3,(H,39,40)/t15-,16+,17+,19+,21-,22+,23-,24+,25-,27+,29+,30+,31-,32-/m1/s1

InChI Key

FYIKIBQJAJRKQM-WNCNYDOCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus aurantium	LOTUS Database	35616633
Citrus iyo	LOTUS Database	35616633
Citrus junos	LOTUS Database	35616633
Citrus macrophylla	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Citrus sinensis	LOTUS Database	35616633
Vitis	FooDB	PHYTOHUB

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
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Oxane
Monosaccharide
Tetrahydrofuran
Heteroaromatic compound
Furan
Secondary alcohol
Ketone
Carboxylic acid ester
Lactone
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:16063 )
Limonoids (C06740 )

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	1.07	ALOGPS
logP	0.022	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.97	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	214.95 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	150.62 m³·mol⁻¹	ChemAxon
Polarizability	64.26 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

C06740

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24820753

PDB ID

Not Available

ChEBI ID

16063

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Linalool (8-hydroxydihydro-) (NP0050129)

MOL for NP0050129 (Linalool (8-hydroxydihydro-))

3D MOL for NP0050129 (Linalool (8-hydroxydihydro-))

3D SDF for NP0050129 (Linalool (8-hydroxydihydro-))

3D-SDF for NP0050129 (Linalool (8-hydroxydihydro-))

PDB for NP0050129 (Linalool (8-hydroxydihydro-))

3D PDB for NP0050129 (Linalool (8-hydroxydihydro-))

SMILES for NP0050129 (Linalool (8-hydroxydihydro-))

INCHI for NP0050129 (Linalool (8-hydroxydihydro-))

Structure for NP0050129 (Linalool (8-hydroxydihydro-))

3D Structure for NP0050129 (Linalool (8-hydroxydihydro-))