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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:27:10 UTC

Update Date

2022-03-07 02:55:39 UTC

HMDB ID

HMDB0038170

Secondary Accession Numbers

HMDB38170

Metabolite Identification

Common Name

Isolimonic acid

Description

Isolimonic acid, also known as isolimonate, belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Isolimonic acid has been detected, but not quantified in, citrus. This could make isolimonic acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Isolimonic acid.

Structure

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


  Mrv0541 01251306532D          

 36 40  0  0  0  0            999 V2000
   -3.0643    0.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    0.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788   -0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643   -0.9822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3498   -0.5697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3498    0.2554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6354    0.6679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6354   -0.9822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9209   -0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9209    0.2554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788   -2.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643   -1.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779   -0.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7628   -1.3947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779   -2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0643   -0.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498   -1.3947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4932    0.4468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7307   -0.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028   -1.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064   -0.1572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  7 21  1  6  0  0  0
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  9 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END

HMDB0038170
     RDKit          3D
Isolimonic acid
 70 74  0  0  0  0  0  0  0  0999 V2000
   -4.8663    1.1036    1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622    1.2121    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 01251306532D          

 36 40  0  0  0  0            999 V2000
   -3.0643    0.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    0.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 25  1  1  0  0  0
  6 26  1  6  0  0  0
 15 27  1  0  0  0  0
 15 28  1  0  0  0  0
 17 29  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  9 32  2  0  0  0  0
  9 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038170

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC[C@]2(C(O)CC(O)=O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]11O[C@@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O10/c1-22(2)15-9-16(27)24(4)14(25(15,12-35-22)17(28)10-18(29)30)5-7-23(3,19(31)13-6-8-34-11-13)26(24)20(36-26)21(32)33/h6,8,11,14-15,17,19-20,28,31H,5,7,9-10,12H2,1-4H3,(H,29,30)(H,32,33)/t14?,15?,17?,19-,20+,23-,24-,25+,26+/m0/s1

> <INCHI_KEY>
JSDNZHXBKWCZDG-RWQHKGFASA-N

> <FORMULA>
C26H34O10

> <MOLECULAR_WEIGHT>
506.5422

> <EXACT_MASS>
506.215197308

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
50.86288769671309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3'S,5aR,6R,7S,9bR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(R)-furan-3-yl(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.1282488916666646

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.403978581310532

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7256940790239303

> <JCHEM_PKA_STRONGEST_BASIC>
-3.087644635117157

> <JCHEM_POLAR_SURFACE_AREA>
167.02999999999997

> <JCHEM_REFRACTIVITY>
121.70359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3'S,5aR,6R,7S,9bR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(R)-furan-3-yl(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxo-hexahydrospiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038170
     RDKit          3D
Isolimonic acid
 70 74  0  0  0  0  0  0  0  0999 V2000
   -4.8663    1.1036    1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622    1.2121    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8723    2.5879   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968    0.2623   -0.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6871   -0.0112   -1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0231   -0.3638   -0.1652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7712   -1.5314    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567   -1.9849    1.6249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001   -2.5779   -0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9209   -3.6769    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1273   -3.6217    1.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3838   -4.7809   -0.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572    0.8721    0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4044    1.9395    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500    1.8396   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    2.7985   -1.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354    0.5912   -0.7895 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2715    0.3164   -2.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802   -0.4514   -0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240   -1.7190   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530   -1.7178    0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2593   -0.5124    0.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6017   -0.1544    1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963   -1.1085   -0.2670 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1825   -1.6742   -1.5341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7736   -0.4862   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3737    0.3255   -1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6409    0.6865   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004    0.1278    0.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7342   -0.5797    0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    0.6835   -0.2878 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6092    1.0702   -1.4042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294    1.9873   -0.4296 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1666    2.7639    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0239    2.2646    1.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414    4.1478    0.3245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3620    2.0779    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6691    0.4097    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474    0.7924    2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038    3.3524    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    2.7291   -1.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9623    2.7062   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944   -0.8103   -2.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964    0.9040   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7741   -1.0682    0.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508   -2.9088    1.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4574   -2.9903   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822   -2.1199   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334   -5.3699   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646    0.4830    1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    2.9463    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998    1.7354    1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2680   -0.0495   -2.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4689   -0.4080   -2.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661    1.3080   -2.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590   -0.2291    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846   -2.6535   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -1.7670   -1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9389   -1.8395    1.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8509   -2.6945    0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -0.9619    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0394    0.7542    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6458   -0.1769    2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6046   -2.1068    0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4174   -1.0614   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699    0.6937   -2.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3750    1.3138   -1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078   -1.1142    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5804    2.7639   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    4.7318    1.1095 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  1
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 22 31  1  0
 31 32  1  6
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 13  2  1  0
 31 17  1  0
 19  6  1  0
 30 26  2  0
 33 31  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
  5 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  1
 25 65  1  0
 27 66  1  0
 28 67  1  0
 30 68  1  0
 33 69  1  6
 36 70  1  0
M  END

HEADER    PROTEIN                                 25-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-13         0                                  
HETATM    1  C   UNK     0      -5.720   1.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.054   0.477   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.054  -1.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.720  -1.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.386  -1.063   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.386   0.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.053   1.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.053  -1.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.719  -1.063   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.719   0.477   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -7.054  -4.143   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.720  -3.373   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.852  -1.357   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -10.757  -2.603   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.852  -3.849   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.387  -3.373   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.387  -1.833   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.283   5.156   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.823   5.156   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.299   3.692   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.053   2.787   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.807   3.692   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.386  -4.143   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.720  -0.293   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.386  -2.603   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.386   2.017   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.941  -4.938   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.454  -5.337   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.157  -0.500   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.387   0.834   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -10.697  -0.500   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.752  -2.200   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.385  -0.293   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -11.467   0.834   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -13.007   0.834   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -10.697   2.168   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2   17    4                                                  
CONECT    4    5    3   12   24                                             
CONECT    5    4    6    8   25                                             
CONECT    6    1    7    5   26                                             
CONECT    7    6   10   21                                                  
CONECT    8    5    9   25                                                  
CONECT    9    8   32   33                                                  
CONECT   10    7                                                            
CONECT   11   16   12                                                       
CONECT   12    4   11   23                                                  
CONECT   13   14   17                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   27   28                                             
CONECT   16   11   15   17                                                  
CONECT   17    3   13   16   29                                             
CONECT   18   19   22                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21    7   20   22                                                  
CONECT   22   21   18                                                       
CONECT   23   12                                                            
CONECT   24    4                                                            
CONECT   25    5    8                                                       
CONECT   26    6                                                            
CONECT   27   15                                                            
CONECT   28   15                                                            
CONECT   29   17   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   34                                                       
CONECT   32    9                                                            
CONECT   33    9                                                            
CONECT   34   31   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0038170
HETATM    1  C1  UNL     1      -4.866   1.104   1.117  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.762   1.212   0.069  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.872   2.588  -0.528  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.997   0.262  -0.959  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.687  -0.011  -1.445  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.023  -0.364  -0.165  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.771  -1.531   0.427  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.257  -1.985   1.625  1.00  0.00           O  
HETATM    9  C7  UNL     1      -3.200  -2.578  -0.543  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.921  -3.677   0.122  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.127  -3.622   1.354  1.00  0.00           O  
HETATM   12  O4  UNL     1      -4.384  -4.781  -0.572  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.457   0.872   0.675  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.404   1.939   0.657  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.550   1.840  -0.591  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.578   2.799  -1.337  1.00  0.00           O  
HETATM   17  C12 UNL     1       0.235   0.591  -0.789  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.271   0.316  -2.288  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.580  -0.451  -0.059  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.124  -1.719  -0.396  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.353  -1.718   0.465  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.259  -0.512   0.348  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.602  -0.154   1.783  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.496  -1.109  -0.267  1.00  0.00           C  
HETATM   25  O6  UNL     1       3.182  -1.674  -1.534  1.00  0.00           O  
HETATM   26  C20 UNL     1       4.774  -0.486  -0.215  1.00  0.00           C  
HETATM   27  C21 UNL     1       5.374   0.326  -1.143  1.00  0.00           C  
HETATM   28  C22 UNL     1       6.641   0.686  -0.666  1.00  0.00           C  
HETATM   29  O7  UNL     1       6.800   0.128   0.480  1.00  0.00           O  
HETATM   30  C23 UNL     1       5.734  -0.580   0.804  1.00  0.00           C  
HETATM   31  C24 UNL     1       1.672   0.683  -0.288  1.00  0.00           C  
HETATM   32  O8  UNL     1       2.609   1.070  -1.404  1.00  0.00           O  
HETATM   33  C25 UNL     1       2.229   1.987  -0.430  1.00  0.00           C  
HETATM   34  C26 UNL     1       3.167   2.764   0.354  1.00  0.00           C  
HETATM   35  O9  UNL     1       4.024   2.265   1.079  1.00  0.00           O  
HETATM   36  O10 UNL     1       3.141   4.148   0.324  1.00  0.00           O  
HETATM   37  H1  UNL     1      -5.362   2.078   1.305  1.00  0.00           H  
HETATM   38  H2  UNL     1      -5.669   0.410   0.774  1.00  0.00           H  
HETATM   39  H3  UNL     1      -4.447   0.792   2.110  1.00  0.00           H  
HETATM   40  H4  UNL     1      -3.704   3.352   0.248  1.00  0.00           H  
HETATM   41  H5  UNL     1      -3.319   2.729  -1.456  1.00  0.00           H  
HETATM   42  H6  UNL     1      -4.962   2.706  -0.809  1.00  0.00           H  
HETATM   43  H7  UNL     1      -2.794  -0.810  -2.180  1.00  0.00           H  
HETATM   44  H8  UNL     1      -2.396   0.904  -1.943  1.00  0.00           H  
HETATM   45  H9  UNL     1      -3.774  -1.068   0.753  1.00  0.00           H  
HETATM   46  H10 UNL     1      -1.951  -2.909   1.540  1.00  0.00           H  
HETATM   47  H11 UNL     1      -2.457  -2.990  -1.212  1.00  0.00           H  
HETATM   48  H12 UNL     1      -3.982  -2.120  -1.241  1.00  0.00           H  
HETATM   49  H13 UNL     1      -3.833  -5.370  -1.152  1.00  0.00           H  
HETATM   50  H14 UNL     1      -2.565   0.483   1.709  1.00  0.00           H  
HETATM   51  H15 UNL     1      -1.784   2.946   0.787  1.00  0.00           H  
HETATM   52  H16 UNL     1      -0.700   1.735   1.497  1.00  0.00           H  
HETATM   53  H17 UNL     1       1.268  -0.050  -2.607  1.00  0.00           H  
HETATM   54  H18 UNL     1      -0.469  -0.408  -2.617  1.00  0.00           H  
HETATM   55  H19 UNL     1       0.166   1.308  -2.822  1.00  0.00           H  
HETATM   56  H20 UNL     1      -0.359  -0.229   1.038  1.00  0.00           H  
HETATM   57  H21 UNL     1      -0.385  -2.653  -0.200  1.00  0.00           H  
HETATM   58  H22 UNL     1       0.485  -1.767  -1.445  1.00  0.00           H  
HETATM   59  H23 UNL     1       0.939  -1.839   1.516  1.00  0.00           H  
HETATM   60  H24 UNL     1       1.851  -2.694   0.297  1.00  0.00           H  
HETATM   61  H25 UNL     1       2.139  -0.962   2.436  1.00  0.00           H  
HETATM   62  H26 UNL     1       2.039   0.754   2.110  1.00  0.00           H  
HETATM   63  H27 UNL     1       3.646  -0.177   2.042  1.00  0.00           H  
HETATM   64  H28 UNL     1       3.605  -2.107   0.341  1.00  0.00           H  
HETATM   65  H29 UNL     1       3.417  -1.061  -2.265  1.00  0.00           H  
HETATM   66  H30 UNL     1       5.070   0.694  -2.111  1.00  0.00           H  
HETATM   67  H31 UNL     1       7.375   1.314  -1.141  1.00  0.00           H  
HETATM   68  H32 UNL     1       5.708  -1.114   1.736  1.00  0.00           H  
HETATM   69  H33 UNL     1       1.580   2.764  -1.000  1.00  0.00           H  
HETATM   70  H34 UNL     1       3.375   4.732   1.110  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    4   13
CONECT    3   40   41   42
CONECT    4    5
CONECT    5    6   43   44
CONECT    6    7   13   19
CONECT    7    8    9   45
CONECT    8   46
CONECT    9   10   47   48
CONECT   10   11   11   12
CONECT   12   49
CONECT   13   14   50
CONECT   14   15   51   52
CONECT   15   16   16   17
CONECT   17   18   19   31
CONECT   18   53   54   55
CONECT   19   20   56
CONECT   20   21   57   58
CONECT   21   22   59   60
CONECT   22   23   24   31
CONECT   23   61   62   63
CONECT   24   25   26   64
CONECT   25   65
CONECT   26   27   30   30
CONECT   27   28   28   66
CONECT   28   29   67
CONECT   29   30
CONECT   30   68
CONECT   31   32   33
CONECT   32   33
CONECT   33   34   69
CONECT   34   35   35   36
CONECT   36   70
END

HMDB0038170
     RDKit          3D
Isolimonic acid
 70 74  0  0  0  0  0  0  0  0999 V2000
   -4.8663    1.1036    1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622    1.2121    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8723    2.5879   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968    0.2623   -0.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6871   -0.0112   -1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0231   -0.3638   -0.1652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7712   -1.5314    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567   -1.9849    1.6249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001   -2.5779   -0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9209   -3.6769    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1273   -3.6217    1.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3838   -4.7809   -0.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572    0.8721    0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4044    1.9395    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500    1.8396   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    2.7985   -1.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354    0.5912   -0.7895 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2715    0.3164   -2.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802   -0.4514   -0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240   -1.7190   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530   -1.7178    0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2593   -0.5124    0.3483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6017   -0.1544    1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963   -1.1085   -0.2670 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1825   -1.6742   -1.5341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7736   -0.4862   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3737    0.3255   -1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6409    0.6865   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004    0.1278    0.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7342   -0.5797    0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    0.6835   -0.2878 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6092    1.0702   -1.4042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294    1.9873   -0.4296 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1666    2.7639    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0239    2.2646    1.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414    4.1478    0.3245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3620    2.0779    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6691    0.4097    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474    0.7924    2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038    3.3524    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    2.7291   -1.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9623    2.7062   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944   -0.8103   -2.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964    0.9040   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7741   -1.0682    0.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508   -2.9088    1.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4574   -2.9903   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822   -2.1199   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334   -5.3699   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646    0.4830    1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    2.9463    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998    1.7354    1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2680   -0.0495   -2.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4689   -0.4080   -2.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661    1.3080   -2.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590   -0.2291    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846   -2.6535   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -1.7670   -1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9389   -1.8395    1.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8509   -2.6945    0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -0.9619    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0394    0.7542    2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6458   -0.1769    2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6046   -2.1068    0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4174   -1.0614   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699    0.6937   -2.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3750    1.3138   -1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078   -1.1142    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5804    2.7639   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    4.7318    1.1095 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  1
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 22 31  1  0
 31 32  1  6
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 13  2  1  0
 31 17  1  0
 19  6  1  0
 30 26  2  0
 33 31  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
  5 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  1
 25 65  1  0
 27 66  1  0
 28 67  1  0
 30 68  1  0
 33 69  1  6
 36 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isolimonate	Generator
(3's,5AR,6R,7S,9BR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(R)-(furan-3-yl)(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylate	HMDB

Chemical Formula

C₂₆H₃₄O₁₀

Average Molecular Weight

506.5422

Monoisotopic Molecular Weight

506.215197308

IUPAC Name

(3'S,5aR,6R,7S,9bR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(R)-furan-3-yl(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

Traditional Name

(3'S,5aR,6R,7S,9bR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(R)-furan-3-yl(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxo-hexahydrospiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)OC[C@]2(C(O)CC(O)=O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]11O[C@@H]1C(O)=O

InChI Identifier

InChI=1S/C26H34O10/c1-22(2)15-9-16(27)24(4)14(25(15,12-35-22)17(28)10-18(29)30)5-7-23(3,19(31)13-6-8-34-11-13)26(24)20(36-26)21(32)33/h6,8,11,14-15,17,19-20,28,31H,5,7,9-10,12H2,1-4H3,(H,29,30)(H,32,33)/t14?,15?,17?,19-,20+,23-,24-,25+,26+/m0/s1

InChI Key

JSDNZHXBKWCZDG-RWQHKGFASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Carbocyclic fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Heteroaromatic compound
Furan
Tetrahydrofuran
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aromatic alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038170)
Cytoplasm (HMDB: HMDB0038170)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038170)

Source

Exogenous

Food

Food (HMDB: HMDB0038170)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0038170)

Not Available

Nutrient (HMDB: HMDB0038170)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038170)

Emulsifier (HMDB: HMDB0038170)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.13	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	167.03 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.7 m³·mol⁻¹	ChemAxon
Polarizability	50.86 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	212.884	31661259
DarkChem	[M-H]-	203.767	31661259
DeepCCS	[M-2H]-	238.993	30932474
DeepCCS	[M+Na]+	213.184	30932474
AllCCS	[M+H]+	213.7	32859911
AllCCS	[M+H-H2O]+	211.9	32859911
AllCCS	[M+NH4]+	215.2	32859911
AllCCS	[M+Na]+	215.7	32859911
AllCCS	[M-H]-	218.1	32859911
AllCCS	[M+Na-2H]-	219.7	32859911
AllCCS	[M+HCOO]-	221.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isolimonic acid	CC1(C)OC[C@]2(C(O)CC(O)=O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]11O[C@@H]1C(O)=O	4121.9	Standard polar	33892256
Isolimonic acid	CC1(C)OC[C@]2(C(O)CC(O)=O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]11O[C@@H]1C(O)=O	3407.3	Standard non polar	33892256
Isolimonic acid	CC1(C)OC[C@]2(C(O)CC(O)=O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]11O[C@@H]1C(O)=O	3988.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isolimonic acid,1TMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3634.3	Semi standard non polar	33892256
Isolimonic acid,1TMS,isomer #2	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3670.2	Semi standard non polar	33892256
Isolimonic acid,1TMS,isomer #3	CC1(C)OC[C@]2(C(O)CC(=O)O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3636.8	Semi standard non polar	33892256
Isolimonic acid,1TMS,isomer #4	CC1(C)OC[C@]2(C(O)CC(=O)O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3643.6	Semi standard non polar	33892256
Isolimonic acid,1TMS,isomer #5	CC1(C)OC[C@]2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3632.2	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3567.1	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #10	CC1(C)OC[C@]2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3517.3	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #2	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3556.9	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #3	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3536.0	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #4	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3540.6	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #5	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3563.6	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #6	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3552.9	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #7	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3537.6	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #8	CC1(C)OC[C@]2(C(O)CC(=O)O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3555.1	Semi standard non polar	33892256
Isolimonic acid,2TMS,isomer #9	CC1(C)OC[C@]2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3536.6	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3499.3	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #10	CC1(C)OC[C@]2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3450.4	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #2	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3473.7	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #3	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3461.5	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #4	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3490.0	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #5	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3476.0	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #6	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3447.7	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #7	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3481.9	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #8	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3453.1	Semi standard non polar	33892256
Isolimonic acid,3TMS,isomer #9	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3424.3	Semi standard non polar	33892256
Isolimonic acid,4TMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3427.6	Semi standard non polar	33892256
Isolimonic acid,4TMS,isomer #2	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3396.8	Semi standard non polar	33892256
Isolimonic acid,4TMS,isomer #3	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3360.1	Semi standard non polar	33892256
Isolimonic acid,4TMS,isomer #4	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3389.8	Semi standard non polar	33892256
Isolimonic acid,4TMS,isomer #5	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3371.3	Semi standard non polar	33892256
Isolimonic acid,5TMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3313.8	Semi standard non polar	33892256
Isolimonic acid,5TMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)C1C=C(O[Si](C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C	3307.9	Standard non polar	33892256
Isolimonic acid,1TBDMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3880.5	Semi standard non polar	33892256
Isolimonic acid,1TBDMS,isomer #2	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3924.4	Semi standard non polar	33892256
Isolimonic acid,1TBDMS,isomer #3	CC1(C)OC[C@]2(C(O)CC(=O)O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3865.8	Semi standard non polar	33892256
Isolimonic acid,1TBDMS,isomer #4	CC1(C)OC[C@]2(C(O)CC(=O)O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	3901.8	Semi standard non polar	33892256
Isolimonic acid,1TBDMS,isomer #5	CC1(C)OC[C@]2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	3893.5	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4045.4	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #10	CC1(C)OC[C@]2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4002.5	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #2	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4024.2	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #3	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4023.9	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #4	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4010.1	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #5	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4028.1	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #6	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4036.1	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #7	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4020.8	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #8	CC1(C)OC[C@]2(C(O)CC(=O)O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4024.0	Semi standard non polar	33892256
Isolimonic acid,2TBDMS,isomer #9	CC1(C)OC[C@]2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4006.2	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #1	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4177.0	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #10	CC1(C)OC[C@]2(C(O)CC(=O)O)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4096.0	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #2	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4162.8	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #3	CC1(C)OC[C@]2(C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4102.2	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #4	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4183.4	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #5	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4116.8	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #6	CC1(C)OC[C@]2(C(CC(=O)O)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4097.8	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #7	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4150.9	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #8	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O[Si](C)(C)C(C)(C)C)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O	4091.9	Semi standard non polar	33892256
Isolimonic acid,3TBDMS,isomer #9	CC1(C)OC[C@]2(C(O)CC(=O)O[Si](C)(C)C(C)(C)C)C1C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]12O[C@@H]2C(=O)O[Si](C)(C)C(C)(C)C	4082.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isolimonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9141700000-092cc167e5d15e69f1c4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isolimonic acid GC-MS (2 TMS) - 70eV, Positive	splash10-002k-9011033000-3fc04633d52f55108a51	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 - Isolimonic acid 10V, Positive-QTOF	splash10-0079-0000910000-2035b8fc46f2e1bf11e6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 20V, Positive-QTOF	splash10-00dj-1000900000-ef37fbf7710d571b3c71	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 40V, Positive-QTOF	splash10-006t-9301600000-d6693411858fccc68d27	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 10V, Negative-QTOF	splash10-0bt9-2001930000-7080be3a00387f36474c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 20V, Negative-QTOF	splash10-066r-7003900000-3820e530ba61f2c43311	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 40V, Negative-QTOF	splash10-014i-6009600000-6995e1edf6133fd68f3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 10V, Positive-QTOF	splash10-0a4r-0000790000-205e2112673c894cd08e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 20V, Positive-QTOF	splash10-0a4r-0000920000-48b50baf77cbd10b3407	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 40V, Positive-QTOF	splash10-0092-4455900000-4cac8f8a8ae048e8a660	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 10V, Negative-QTOF	splash10-02t9-0000900000-c43d893ec123b082d483	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 20V, Negative-QTOF	splash10-014i-0005900000-494588f2be395dd8ff9b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isolimonic acid 40V, Negative-QTOF	splash10-00r6-9001200000-020f8fd3d1ae87b74483	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB017401

KNApSAcK ID

Not Available

Chemspider ID

35014526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752314

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isolimonic acid (HMDB0038170)

MOL for HMDB0038170 (Isolimonic acid)

3D MOL for HMDB0038170 (Isolimonic acid)

3D SDF for HMDB0038170 (Isolimonic acid)

3D-SDF for HMDB0038170 (Isolimonic acid)

PDB for HMDB0038170 (Isolimonic acid)

3D PDB for HMDB0038170 (Isolimonic acid)

SMILES for HMDB0038170 (Isolimonic acid)

INCHI for HMDB0038170 (Isolimonic acid)

Structure for HMDB0038170 (Isolimonic acid)

3D Structure for HMDB0038170 (Isolimonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra