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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:08:41 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036075

Secondary Accession Numbers

HMDB36075

Metabolite Identification

Common Name

Limonexic acid

Description

Limonexic acid, also known as limonexate, 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 a significant number of articles have been published on Limonexic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061308532D          

 36 42  0  0  0  0            999 V2000
    1.1556    0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    0.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6064    3.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994    2.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    3.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6488    3.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043    2.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4185    3.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7018    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906    1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1154    3.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1103    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9215    0.3886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667    2.9732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4619    4.5360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    1.7952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6  5  1  0  0  0  0
 11  7  2  0  0  0  0
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 36 19  1  0  0  0  0
 36 26  1  0  0  0  0
M  END

HMDB0036075
     RDKit          3D
Limonexic acid
 66 72  0  0  0  0  0  0  0  0999 V2000
   -3.0696    2.6246    1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3664    1.1936    0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8054   -0.9633    0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061308532D          

 36 42  0  0  0  0            999 V2000
    1.1556    0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    0.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6064    3.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4994    2.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9821    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0036075

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(=O)OC1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O10/c1-22(2)13-8-14(27)24(4)12(25(13)10-32-16(28)9-15(25)35-22)5-6-23(3)18(11-7-17(29)33-20(11)30)34-21(31)19-26(23,24)36-19/h7,12-13,15,18-20,30H,5-6,8-10H2,1-4H3

> <INCHI_KEY>
RTPPVNISJHFPFX-UHFFFAOYSA-N

> <FORMULA>
C26H30O10

> <MOLECULAR_WEIGHT>
502.5104

> <EXACT_MASS>
502.18389718

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
49.47688675667672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.246031333999998

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.73022841805401

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.303217313744015

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9482194429242328

> <JCHEM_POLAR_SURFACE_AREA>
137.96

> <JCHEM_REFRACTIVITY>
117.66589999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-(2-hydroxy-5-oxo-2H-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036075
     RDKit          3D
Limonexic acid
 66 72  0  0  0  0  0  0  0  0999 V2000
   -3.0696    2.6246    1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3664    1.1936    0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485    0.8716    1.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2110    1.2005   -0.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8181   -0.0456   -1.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846   -0.7817   -1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6302   -2.1277   -2.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9939   -2.6430   -3.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -2.7402   -1.1305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -2.0895    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278   -0.7149   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3260    0.2059    1.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1581    0.9727    1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934    0.2259    1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738    0.5014    2.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397   -0.9385    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -2.1254    1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -0.8741   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1821    0.1977   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2214    0.6860   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1672   -0.4412   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626   -1.6128   -1.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484    0.0380   -1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9049    1.3921   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2880    2.3546   -1.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596    3.5567   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9435    4.6811   -1.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211    3.2661    0.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989    1.9418    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231    1.2482    1.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -0.9382   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -2.0633    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -3.1453   -0.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6972   -2.0108    0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6228   -0.8132    1.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8054   -0.9633    0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0513    3.1832    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769    2.6816    2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4084    3.1571    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0088    1.5163    2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5130    1.1411    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8526   -0.1654    1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2868    0.0858   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4912   -0.2606   -2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8410   -0.8469   -0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109   -1.9947    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660   -2.7804    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857   -0.4048    1.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499    1.9325    1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4204    1.2630    2.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.0905    2.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382   -1.9550    2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1598   -3.0943    1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892   -1.8730   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317    1.1044   -1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121   -0.0922   -2.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    1.1830   -2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829    1.4507   -0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -1.8047   -2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7590   -2.5631   -1.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712   -1.4425   -2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960   -0.0230   -2.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993    2.3060   -2.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9353    1.8372    1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7449    1.4227    0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811   -2.9631    1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 23 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 12  2  1  0
 36 16  1  0
 11  5  1  0
 36 21  1  0
 18 11  1  0
 29 24  1  0
 36 34  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 25 63  1  0
 29 64  1  0
 30 65  1  0
 34 66  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.157   0.510   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.784   1.775   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.865   5.706   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.799   3.807   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.833   5.164   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.349   5.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.861   6.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.264   0.818   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.211   5.915   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.128   4.222   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.381   5.977   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.310   3.715   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.729   1.996   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.779   1.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.422   4.389   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.215   6.495   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.911   7.944   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.858   4.528   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.812   1.632   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.517   7.251   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.327   1.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.268   2.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.342   4.257   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.303   2.538   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.206   3.444   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.819   2.809   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.772  -0.088   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.426   8.021   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -9.185   8.808   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -3.978   7.301   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -7.320   0.725   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.431   5.550   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.462   8.467   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.851   3.351   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.696   3.525   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -3.296   1.361   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5    6   12                                                       
CONECT    6    5   23                                                       
CONECT    7   11   17                                                       
CONECT    8   13   14                                                       
CONECT    9   15   16                                                       
CONECT   10   25   32                                                       
CONECT   11    7   18   20                                                  
CONECT   12    5   24   25                                                  
CONECT   13    8   22   25                                                  
CONECT   14    8   24   27                                                  
CONECT   15    9   25   35                                                  
CONECT   16    9   28   32                                                  
CONECT   17    7   29   33                                                  
CONECT   18   11   23   34                                                  
CONECT   19   21   26   36                                                  
CONECT   20   11   30   33                                                  
CONECT   21   19   31   34                                                  
CONECT   22    1    2   13   35                                             
CONECT   23    3    6   18   26                                             
CONECT   24    4   12   14   26                                             
CONECT   25   10   12   13   15                                             
CONECT   26   19   23   24   36                                             
CONECT   27   14                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   20                                                            
CONECT   31   21                                                            
CONECT   32   10   16                                                       
CONECT   33   17   20                                                       
CONECT   34   18   21                                                       
CONECT   35   15   22                                                       
CONECT   36   19   26                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

COMPND    HMDB0036075
HETATM    1  C1  UNL     1      -3.070   2.625   1.151  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.366   1.194   0.680  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.748   0.872   1.176  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.211   1.200  -0.673  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.818  -0.046  -1.114  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.085  -0.782  -1.502  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.630  -2.128  -2.005  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.994  -2.643  -3.065  1.00  0.00           O  
HETATM    9  O3  UNL     1      -2.740  -2.740  -1.130  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.681  -2.089   0.152  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.028  -0.715  -0.011  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.326   0.206   1.136  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.158   0.973   1.656  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.093   0.226   1.748  1.00  0.00           C  
HETATM   15  O4  UNL     1       0.974   0.501   2.542  1.00  0.00           O  
HETATM   16  C12 UNL     1       0.340  -0.938   0.842  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.122  -2.125   1.760  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.566  -0.874  -0.318  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.182   0.198  -1.280  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.221   0.686  -1.155  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.167  -0.441  -0.818  1.00  0.00           C  
HETATM   22  C18 UNL     1       1.963  -1.613  -1.795  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.548   0.038  -1.056  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.905   1.392  -0.655  1.00  0.00           C  
HETATM   25  C21 UNL     1       4.288   2.355  -1.477  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.560   3.557  -0.711  1.00  0.00           C  
HETATM   27  O5  UNL     1       4.944   4.681  -1.132  1.00  0.00           O  
HETATM   28  O6  UNL     1       4.321   3.266   0.617  1.00  0.00           O  
HETATM   29  C23 UNL     1       3.899   1.942   0.705  1.00  0.00           C  
HETATM   30  O7  UNL     1       4.923   1.248   1.402  1.00  0.00           O  
HETATM   31  O8  UNL     1       4.453  -0.938  -0.504  1.00  0.00           O  
HETATM   32  C24 UNL     1       3.936  -2.063   0.110  1.00  0.00           C  
HETATM   33  O9  UNL     1       4.533  -3.145  -0.042  1.00  0.00           O  
HETATM   34  C25 UNL     1       2.697  -2.011   0.937  1.00  0.00           C  
HETATM   35  O10 UNL     1       2.623  -0.813   1.649  1.00  0.00           O  
HETATM   36  C26 UNL     1       1.805  -0.963   0.511  1.00  0.00           C  
HETATM   37  H1  UNL     1      -4.051   3.183   1.081  1.00  0.00           H  
HETATM   38  H2  UNL     1      -2.777   2.682   2.195  1.00  0.00           H  
HETATM   39  H3  UNL     1      -2.408   3.157   0.438  1.00  0.00           H  
HETATM   40  H4  UNL     1      -5.009   1.516   2.069  1.00  0.00           H  
HETATM   41  H5  UNL     1      -5.513   1.141   0.418  1.00  0.00           H  
HETATM   42  H6  UNL     1      -4.853  -0.165   1.559  1.00  0.00           H  
HETATM   43  H7  UNL     1      -2.287   0.086  -2.056  1.00  0.00           H  
HETATM   44  H8  UNL     1      -4.491  -0.261  -2.380  1.00  0.00           H  
HETATM   45  H9  UNL     1      -4.841  -0.847  -0.737  1.00  0.00           H  
HETATM   46  H10 UNL     1      -3.711  -1.995   0.509  1.00  0.00           H  
HETATM   47  H11 UNL     1      -2.166  -2.780   0.792  1.00  0.00           H  
HETATM   48  H12 UNL     1      -2.786  -0.405   1.940  1.00  0.00           H  
HETATM   49  H13 UNL     1      -0.950   1.932   1.150  1.00  0.00           H  
HETATM   50  H14 UNL     1      -1.420   1.263   2.718  1.00  0.00           H  
HETATM   51  H15 UNL     1       0.989  -2.090   2.490  1.00  0.00           H  
HETATM   52  H16 UNL     1      -0.738  -1.955   2.469  1.00  0.00           H  
HETATM   53  H17 UNL     1       0.160  -3.094   1.290  1.00  0.00           H  
HETATM   54  H18 UNL     1      -0.489  -1.873  -0.848  1.00  0.00           H  
HETATM   55  H19 UNL     1      -0.832   1.104  -1.087  1.00  0.00           H  
HETATM   56  H20 UNL     1      -0.312  -0.092  -2.365  1.00  0.00           H  
HETATM   57  H21 UNL     1       1.517   1.183  -2.121  1.00  0.00           H  
HETATM   58  H22 UNL     1       1.283   1.451  -0.391  1.00  0.00           H  
HETATM   59  H23 UNL     1       2.887  -1.805  -2.400  1.00  0.00           H  
HETATM   60  H24 UNL     1       1.759  -2.563  -1.264  1.00  0.00           H  
HETATM   61  H25 UNL     1       1.171  -1.443  -2.517  1.00  0.00           H  
HETATM   62  H26 UNL     1       3.696  -0.023  -2.190  1.00  0.00           H  
HETATM   63  H27 UNL     1       4.399   2.306  -2.568  1.00  0.00           H  
HETATM   64  H28 UNL     1       2.935   1.837   1.248  1.00  0.00           H  
HETATM   65  H29 UNL     1       5.745   1.423   0.870  1.00  0.00           H  
HETATM   66  H30 UNL     1       2.381  -2.963   1.359  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    4   12
CONECT    3   40   41   42
CONECT    4    5
CONECT    5    6   11   43
CONECT    6    7   44   45
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   46   47
CONECT   11   12   18
CONECT   12   13   48
CONECT   13   14   49   50
CONECT   14   15   15   16
CONECT   16   17   18   36
CONECT   17   51   52   53
CONECT   18   19   54
CONECT   19   20   55   56
CONECT   20   21   57   58
CONECT   21   22   23   36
CONECT   22   59   60   61
CONECT   23   24   31   62
CONECT   24   25   25   29
CONECT   25   26   63
CONECT   26   27   27   28
CONECT   28   29
CONECT   29   30   64
CONECT   30   65
CONECT   31   32
CONECT   32   33   33   34
CONECT   34   35   36   66
CONECT   35   36
END

HMDB0036075
     RDKit          3D
Limonexic acid
 66 72  0  0  0  0  0  0  0  0999 V2000
   -3.0696    2.6246    1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3664    1.1936    0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485    0.8716    1.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2110    1.2005   -0.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8181   -0.0456   -1.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846   -0.7817   -1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6302   -2.1277   -2.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9939   -2.6430   -3.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -2.7402   -1.1305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -2.0895    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0278   -0.7149   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3260    0.2059    1.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1581    0.9727    1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934    0.2259    1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738    0.5014    2.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397   -0.9385    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -2.1254    1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660   -0.8741   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1821    0.1977   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2214    0.6860   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1672   -0.4412   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626   -1.6128   -1.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484    0.0380   -1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9049    1.3921   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2880    2.3546   -1.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596    3.5567   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9435    4.6811   -1.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211    3.2661    0.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989    1.9418    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9231    1.2482    1.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -0.9382   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -2.0633    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -3.1453   -0.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6972   -2.0108    0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6228   -0.8132    1.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8054   -0.9633    0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0513    3.1832    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769    2.6816    2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4084    3.1571    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0088    1.5163    2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5130    1.1411    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8526   -0.1654    1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2868    0.0858   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4912   -0.2606   -2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8410   -0.8469   -0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109   -1.9947    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660   -2.7804    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857   -0.4048    1.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499    1.9325    1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4204    1.2630    2.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.0905    2.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382   -1.9550    2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1598   -3.0943    1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892   -1.8730   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317    1.1044   -1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121   -0.0922   -2.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    1.1830   -2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829    1.4507   -0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -1.8047   -2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7590   -2.5631   -1.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712   -1.4425   -2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960   -0.0230   -2.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993    2.3060   -2.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9353    1.8372    1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7449    1.4227    0.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811   -2.9631    1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 23 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 12  2  1  0
 36 16  1  0
 11  5  1  0
 36 21  1  0
 18 11  1  0
 29 24  1  0
 36 34  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 25 63  1  0
 29 64  1  0
 30 65  1  0
 34 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Limonexate	Generator
Limonexin	HMDB
Shihulimonin a	HMDB

Chemical Formula

C₂₆H₃₀O₁₀

Average Molecular Weight

502.5104

Monoisotopic Molecular Weight

502.18389718

IUPAC Name

19-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

Traditional Name

19-(2-hydroxy-5-oxo-2H-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

CAS Registry Number

99026-99-0

SMILES

CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(=O)OC1O

InChI Identifier

InChI=1S/C26H30O10/c1-22(2)13-8-14(27)24(4)12(25(13)10-32-16(28)9-15(25)35-22)5-6-23(3)18(11-7-17(29)33-20(11)30)34-21(31)19-26(23,24)36-19/h7,12-13,15,18-20,30H,5-6,8-10H2,1-4H3

InChI Key

RTPPVNISJHFPFX-UHFFFAOYSA-N

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 lactone
11-oxosteroid
Oxosteroid
2-oxosteroid
Steroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Oxane
Pyran
2-furanone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Dihydrofuran
Carboxylic acid ester
Lactone
Ketone
Hemiacetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0036075)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0036075)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036075)

Source

Endogenous

Endogenous (HMDB: HMDB0036075)

Plant

Plant (HMDB: HMDB0036075)

Animal

Animal (HMDB: HMDB0036075)

Exogenous

Food

Food (HMDB: HMDB0036075)

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)
Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0036075)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036075)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036075)

Lipid metabolism pathway (HMDB: HMDB0036075)

Cellular process

Cell signaling (HMDB: HMDB0036075)

Biochemical process

Lipid transport (HMDB: HMDB0036075)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036075)

Molecular messenger

Signaling molecule (HMDB: HMDB0036075)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036075)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	285 - 286 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.83	ALOGPS
logP	1.25	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.3	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	117.67 m³·mol⁻¹	ChemAxon
Polarizability	49.48 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	212.58	31661259
DarkChem	[M-H]-	205.113	31661259
DeepCCS	[M-2H]-	232.934	30932474
DeepCCS	[M+Na]+	208.359	30932474
AllCCS	[M+H]+	212.8	32859911
AllCCS	[M+H-H2O]+	211.1	32859911
AllCCS	[M+NH4]+	214.4	32859911
AllCCS	[M+Na]+	214.9	32859911
AllCCS	[M-H]-	216.6	32859911
AllCCS	[M+Na-2H]-	217.8	32859911
AllCCS	[M+HCOO]-	219.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.73 minutes	32390414
Predicted by Siyang on May 30, 2022	14.297 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3076.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	193.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	123.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	675.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	678.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1073.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	475.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1812.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	235.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	163.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Limonexic acid	CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(=O)OC1O	4048.8	Standard polar	33892256
Limonexic acid	CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(=O)OC1O	3446.7	Standard non polar	33892256
Limonexic acid	CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(=O)OC1O	4513.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Limonexic acid,1TMS,isomer #1	CC1(C)OC2CC(=O)OCC23C1CC(=O)C1(C)C3CCC2(C)C(C3=CC(=O)OC3O[Si](C)(C)C)OC(=O)C3OC321	3964.5	Semi standard non polar	33892256
Limonexic acid,1TMS,isomer #2	CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C)C1(C)C3CCC2(C)C(C3=CC(=O)OC3O)OC(=O)C3OC321	3900.2	Semi standard non polar	33892256
Limonexic acid,2TMS,isomer #1	CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C)C1(C)C3CCC2(C)C(C3=CC(=O)OC3O[Si](C)(C)C)OC(=O)C3OC321	3855.3	Semi standard non polar	33892256
Limonexic acid,2TMS,isomer #1	CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C)C1(C)C3CCC2(C)C(C3=CC(=O)OC3O[Si](C)(C)C)OC(=O)C3OC321	3580.3	Standard non polar	33892256
Limonexic acid,1TBDMS,isomer #1	CC1(C)OC2CC(=O)OCC23C1CC(=O)C1(C)C3CCC2(C)C(C3=CC(=O)OC3O[Si](C)(C)C(C)(C)C)OC(=O)C3OC321	4208.5	Semi standard non polar	33892256
Limonexic acid,1TBDMS,isomer #2	CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C3CCC2(C)C(C3=CC(=O)OC3O)OC(=O)C3OC321	4148.4	Semi standard non polar	33892256
Limonexic acid,2TBDMS,isomer #1	CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C3CCC2(C)C(C3=CC(=O)OC3O[Si](C)(C)C(C)(C)C)OC(=O)C3OC321	4312.9	Semi standard non polar	33892256
Limonexic acid,2TBDMS,isomer #1	CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C3CCC2(C)C(C3=CC(=O)OC3O[Si](C)(C)C(C)(C)C)OC(=O)C3OC321	4001.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Limonexic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-1043900000-70c2fe4a483f77ba0968	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Limonexic acid GC-MS (1 TMS) - 70eV, Positive	splash10-074l-6025090000-3025e08431ce60c8cbf9	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 10V, Positive-QTOF	splash10-0udr-0001930000-e07bb1050cc713e2ca9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 20V, Positive-QTOF	splash10-0k9m-0002900000-077516246d5230a2cdcd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 40V, Positive-QTOF	splash10-01ot-4974100000-de61690f44d7bc867aa5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 10V, Negative-QTOF	splash10-0pb9-0000920000-5fc6cda5ce0caf479d5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 20V, Negative-QTOF	splash10-0a4i-1000900000-57e000a0358b6bd4335d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 40V, Negative-QTOF	splash10-0006-9202500000-6090d00423e79a2d65d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 10V, Negative-QTOF	splash10-0a4i-0000910000-a2eb9909c1dff4907215	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 20V, Negative-QTOF	splash10-0zfr-0000970000-f9edc24e822a85346298	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 40V, Negative-QTOF	splash10-0zor-2000910000-0d32d29d379ae7d2a40e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 10V, Positive-QTOF	splash10-0udi-0000390000-50351e2e43c8a178f386	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 20V, Positive-QTOF	splash10-0zg0-0010950000-5f846ad51591f6faaf25	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limonexic acid 40V, Positive-QTOF	splash10-0h5g-0540910000-088c4d131510c4869042	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014907

KNApSAcK ID

Not Available

Chemspider ID

35014090

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76419898

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1853551

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Limonexic acid (HMDB0036075)

MOL for HMDB0036075 (Limonexic acid)

3D MOL for HMDB0036075 (Limonexic acid)

3D SDF for HMDB0036075 (Limonexic acid)

3D-SDF for HMDB0036075 (Limonexic acid)

PDB for HMDB0036075 (Limonexic acid)

3D PDB for HMDB0036075 (Limonexic acid)

SMILES for HMDB0036075 (Limonexic acid)

INCHI for HMDB0036075 (Limonexic acid)

Structure for HMDB0036075 (Limonexic acid)

3D Structure for HMDB0036075 (Limonexic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra