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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:57:10 UTC

Update Date

2022-03-07 02:55:27 UTC

HMDB ID

HMDB0037691

Secondary Accession Numbers

HMDB37691

Metabolite Identification

Common Name

Limocitrol

Description

Limocitrol belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, limocitrol is considered to be a flavonoid. Limocitrol has been detected, but not quantified in, citrus and lemons (Citrus limon). This could make limocitrol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Limocitrol.

Structure

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


  Mrv0541 05061309572D          

 27 29  0  0  0  0            999 V2000
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  2  0  0  0  0
 17 12  2  0  0  0  0
 17 14  1  0  0  0  0
 18 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19  8  1  0  0  0  0
 20 11  2  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 14  1  0  0  0  0
 24  1  1  0  0  0  0
 24  9  1  0  0  0  0
 25  2  1  0  0  0  0
 25 17  1  0  0  0  0
 26  3  1  0  0  0  0
 26 18  1  0  0  0  0
 27 15  1  0  0  0  0
 27 16  1  0  0  0  0
M  END

HMDB0037691
     RDKit          3D
Limocitrol
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.6334    2.0766    1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998    1.0207    0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    0.3312   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    0.6068    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -0.0415   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010    0.2055    0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430   -0.5375   -0.4241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3910   -0.3786   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591   -1.1860   -0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -2.1640   -1.6388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6440   -3.4751   -1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6749   -0.9648   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6662   -1.7462   -0.9662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0328    0.0200    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3717    0.2218    0.8331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1828    1.1205    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    0.8245    1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    1.7988    1.9963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653    0.6155    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376    1.4164    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344    2.3088    2.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    1.1938    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    2.0179    1.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4226   -1.0723   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822   -1.3914   -1.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848   -0.6835   -1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0502   -1.0176   -1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787    1.6234    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    2.6751    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431    2.7411    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173    1.3988    0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -3.5845   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796   -4.2586   -1.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493   -3.6173   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5135   -2.4762   -1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5422    1.6205   -0.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9887    0.6017   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5672    1.8818    0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4677    1.9018    2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    2.7207    2.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5852   -1.6245   -1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169   -2.1953   -2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8548   -0.5288   -1.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 22  6  2  0
 19  8  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 23 40  1  0
 24 41  1  0
 25 42  1  0
 27 43  1  0
M  END


  Mrv0541 05061309572D          

 27 29  0  0  0  0            999 V2000
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  2  0  0  0  0
 17 12  2  0  0  0  0
 17 14  1  0  0  0  0
 18 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19  8  1  0  0  0  0
 20 11  2  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 14  1  0  0  0  0
 24  1  1  0  0  0  0
 24  9  1  0  0  0  0
 25  2  1  0  0  0  0
 25 17  1  0  0  0  0
 26  3  1  0  0  0  0
 26 18  1  0  0  0  0
 27 15  1  0  0  0  0
 27 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037691

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O9/c1-24-9-6-7(4-5-8(9)19)15-13(22)11(20)10-12(21)17(25-2)14(23)18(26-3)16(10)27-15/h4-6,19,21-23H,1-3H3

> <INCHI_KEY>
LCKHNFJHVWUHTR-UHFFFAOYSA-N

> <FORMULA>
C18H16O9

> <MOLECULAR_WEIGHT>
376.3142

> <EXACT_MASS>
376.07943211

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
36.21621684310768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.9868509886666659

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.618687083650004

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.44602097218475

> <JCHEM_PKA_STRONGEST_BASIC>
-4.018658136527205

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
94.2709

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
limocitrol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037691
     RDKit          3D
Limocitrol
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.6334    2.0766    1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998    1.0207    0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    0.3312   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    0.6068    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -0.0415   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010    0.2055    0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430   -0.5375   -0.4241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3910   -0.3786   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591   -1.1860   -0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -2.1640   -1.6388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6440   -3.4751   -1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6749   -0.9648   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6662   -1.7462   -0.9662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0328    0.0200    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3717    0.2218    0.8331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1828    1.1205    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    0.8245    1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    1.7988    1.9963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653    0.6155    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376    1.4164    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344    2.3088    2.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    1.1938    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    2.0179    1.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4226   -1.0723   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822   -1.3914   -1.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848   -0.6835   -1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0502   -1.0176   -1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787    1.6234    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    2.6751    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431    2.7411    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173    1.3988    0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -3.5845   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796   -4.2586   -1.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493   -3.6173   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5135   -2.4762   -1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5422    1.6205   -0.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9887    0.6017   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5672    1.8818    0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4677    1.9018    2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    2.7207    2.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5852   -1.6245   -1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169   -2.1953   -2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8548   -0.5288   -1.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 22  6  2  0
 19  8  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 23 40  1  0
 24 41  1  0
 25 42  1  0
 27 43  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      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6    7    9                                                       
CONECT    7    4    6   15                                                  
CONECT    8    5    9   19                                                  
CONECT    9    6    8   24                                                  
CONECT   10   11   12   16                                                  
CONECT   11   10   13   20                                                  
CONECT   12   10   17   21                                                  
CONECT   13   11   15   22                                                  
CONECT   14   17   18   23                                                  
CONECT   15    7   13   27                                                  
CONECT   16   10   18   27                                                  
CONECT   17   12   14   25                                                  
CONECT   18   14   16   26                                                  
CONECT   19    8                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24    1    9                                                       
CONECT   25    2   17                                                       
CONECT   26    3   18                                                       
CONECT   27   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0037691
HETATM    1  C1  UNL     1       5.633   2.077   1.203  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.700   1.021   0.273  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.613   0.331  -0.206  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.295   0.607   0.185  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.203  -0.041  -0.257  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.801   0.206   0.118  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.143  -0.537  -0.424  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.391  -0.379  -0.144  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.359  -1.186  -0.739  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.958  -2.164  -1.639  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.644  -3.475  -1.193  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.675  -0.965  -0.396  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.666  -1.746  -0.966  1.00  0.00           O  
HETATM   14  C10 UNL     1      -4.033   0.020   0.505  1.00  0.00           C  
HETATM   15  O5  UNL     1      -5.372   0.222   0.833  1.00  0.00           O  
HETATM   16  C11 UNL     1      -6.183   1.120   0.100  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.091   0.825   1.101  1.00  0.00           C  
HETATM   18  O6  UNL     1      -3.484   1.799   1.996  1.00  0.00           O  
HETATM   19  C13 UNL     1      -1.765   0.615   0.767  1.00  0.00           C  
HETATM   20  C14 UNL     1      -0.838   1.416   1.362  1.00  0.00           C  
HETATM   21  O7  UNL     1      -1.134   2.309   2.175  1.00  0.00           O  
HETATM   22  C15 UNL     1       0.506   1.194   1.015  1.00  0.00           C  
HETATM   23  O8  UNL     1       1.426   2.018   1.630  1.00  0.00           O  
HETATM   24  C16 UNL     1       2.423  -1.072  -1.183  1.00  0.00           C  
HETATM   25  C17 UNL     1       3.682  -1.391  -1.605  1.00  0.00           C  
HETATM   26  C18 UNL     1       4.785  -0.684  -1.112  1.00  0.00           C  
HETATM   27  O9  UNL     1       6.050  -1.018  -1.547  1.00  0.00           O  
HETATM   28  H1  UNL     1       5.479   1.623   2.205  1.00  0.00           H  
HETATM   29  H2  UNL     1       6.560   2.675   1.225  1.00  0.00           H  
HETATM   30  H3  UNL     1       4.743   2.741   1.033  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.217   1.399   0.886  1.00  0.00           H  
HETATM   32  H5  UNL     1      -1.970  -3.585  -0.119  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.180  -4.259  -1.755  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.549  -3.617  -1.188  1.00  0.00           H  
HETATM   35  H8  UNL     1      -4.514  -2.476  -1.621  1.00  0.00           H  
HETATM   36  H9  UNL     1      -5.542   1.621  -0.653  1.00  0.00           H  
HETATM   37  H10 UNL     1      -6.989   0.602  -0.453  1.00  0.00           H  
HETATM   38  H11 UNL     1      -6.567   1.882   0.803  1.00  0.00           H  
HETATM   39  H12 UNL     1      -4.468   1.902   2.198  1.00  0.00           H  
HETATM   40  H13 UNL     1       1.140   2.721   2.276  1.00  0.00           H  
HETATM   41  H14 UNL     1       1.585  -1.625  -1.570  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.817  -2.195  -2.322  1.00  0.00           H  
HETATM   43  H16 UNL     1       6.855  -0.529  -1.212  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4   26
CONECT    4    5   31
CONECT    5    6   24   24
CONECT    6    7   22   22
CONECT    7    8
CONECT    8    9    9   19
CONECT    9   10   12
CONECT   10   11
CONECT   11   32   33   34
CONECT   12   13   14   14
CONECT   13   35
CONECT   14   15   17
CONECT   15   16
CONECT   16   36   37   38
CONECT   17   18   19   19
CONECT   18   39
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   40
CONECT   24   25   41
CONECT   25   26   26   42
CONECT   26   27
CONECT   27   43
END

HMDB0037691
     RDKit          3D
Limocitrol
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.6334    2.0766    1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998    1.0207    0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    0.3312   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    0.6068    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -0.0415   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010    0.2055    0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1430   -0.5375   -0.4241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3910   -0.3786   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591   -1.1860   -0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -2.1640   -1.6388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6440   -3.4751   -1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6749   -0.9648   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6662   -1.7462   -0.9662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0328    0.0200    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3717    0.2218    0.8331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1828    1.1205    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    0.8245    1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    1.7988    1.9963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653    0.6155    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376    1.4164    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344    2.3088    2.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    1.1938    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    2.0179    1.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4226   -1.0723   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822   -1.3914   -1.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848   -0.6835   -1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0502   -1.0176   -1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787    1.6234    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    2.6751    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7431    2.7411    1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173    1.3988    0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -3.5845   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796   -4.2586   -1.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493   -3.6173   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5135   -2.4762   -1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5422    1.6205   -0.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9887    0.6017   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5672    1.8818    0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4677    1.9018    2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402    2.7207    2.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5852   -1.6245   -1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169   -2.1953   -2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8548   -0.5288   -1.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 22  6  2  0
 19  8  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 23 40  1  0
 24 41  1  0
 25 42  1  0
 27 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4',5,7-Tetrahydroxy-3',6,8-trimethoxyflavone	HMDB

Chemical Formula

C₁₈H₁₆O₉

Average Molecular Weight

376.3142

Monoisotopic Molecular Weight

376.07943211

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-4H-chromen-4-one

Traditional Name

limocitrol

CAS Registry Number

549-10-0

SMILES

COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O

InChI Identifier

InChI=1S/C18H16O9/c1-24-9-6-7(4-5-8(9)19)15-13(22)11(20)10-12(21)17(25-2)14(23)18(26-3)16(10)27-15/h4-6,19,21-23H,1-3H3

InChI Key

LCKHNFJHVWUHTR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Pyranone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12113333 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037691)
Cytoplasm (HMDB: HMDB0037691)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037691)

Source

Exogenous

Food

Food (HMDB: HMDB0037691)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0037691)

Not Available

Nutrient (HMDB: HMDB0037691)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	221 - 222 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	255.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.02	ALOGPS
logP	1.99	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.45	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.27 m³·mol⁻¹	ChemAxon
Polarizability	36.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	184.973	30932474
DeepCCS	[M-H]-	182.615	30932474
DeepCCS	[M-2H]-	216.328	30932474
DeepCCS	[M+Na]+	191.556	30932474
AllCCS	[M+H]+	185.8	32859911
AllCCS	[M+H-H2O]+	182.7	32859911
AllCCS	[M+NH4]+	188.7	32859911
AllCCS	[M+Na]+	189.5	32859911
AllCCS	[M-H]-	186.5	32859911
AllCCS	[M+Na-2H]-	186.2	32859911
AllCCS	[M+HCOO]-	186.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Limocitrol	COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O	5543.7	Standard polar	33892256
Limocitrol	COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O	3415.0	Standard non polar	33892256
Limocitrol	COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O	3383.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Limocitrol,1TMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C	3502.7	Semi standard non polar	33892256
Limocitrol,1TMS,isomer #2	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C(OC)=C(O)C(OC)=C3O2)=CC=C1O	3478.3	Semi standard non polar	33892256
Limocitrol,1TMS,isomer #3	COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O	3468.9	Semi standard non polar	33892256
Limocitrol,1TMS,isomer #4	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C(OC)=C3O2)=CC=C1O	3478.7	Semi standard non polar	33892256
Limocitrol,2TMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C	3369.3	Semi standard non polar	33892256
Limocitrol,2TMS,isomer #2	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C	3375.7	Semi standard non polar	33892256
Limocitrol,2TMS,isomer #3	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C(OC)=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C	3382.2	Semi standard non polar	33892256
Limocitrol,2TMS,isomer #4	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O	3326.7	Semi standard non polar	33892256
Limocitrol,2TMS,isomer #5	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C(OC)=C3O2)=CC=C1O	3344.0	Semi standard non polar	33892256
Limocitrol,2TMS,isomer #6	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O	3346.3	Semi standard non polar	33892256
Limocitrol,3TMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C	3233.1	Semi standard non polar	33892256
Limocitrol,3TMS,isomer #2	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C	3235.0	Semi standard non polar	33892256
Limocitrol,3TMS,isomer #3	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C	3254.4	Semi standard non polar	33892256
Limocitrol,3TMS,isomer #4	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O	3238.2	Semi standard non polar	33892256
Limocitrol,4TMS,isomer #1	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C	3212.9	Semi standard non polar	33892256
Limocitrol,1TBDMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3722.9	Semi standard non polar	33892256
Limocitrol,1TBDMS,isomer #2	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C(OC)=C(O)C(OC)=C3O2)=CC=C1O	3697.3	Semi standard non polar	33892256
Limocitrol,1TBDMS,isomer #3	COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O	3707.9	Semi standard non polar	33892256
Limocitrol,1TBDMS,isomer #4	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C(OC)=C3O2)=CC=C1O	3706.9	Semi standard non polar	33892256
Limocitrol,2TBDMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3843.5	Semi standard non polar	33892256
Limocitrol,2TBDMS,isomer #2	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3852.4	Semi standard non polar	33892256
Limocitrol,2TBDMS,isomer #3	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C(OC)=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3866.7	Semi standard non polar	33892256
Limocitrol,2TBDMS,isomer #4	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O	3811.6	Semi standard non polar	33892256
Limocitrol,2TBDMS,isomer #5	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C(OC)=C3O2)=CC=C1O	3831.4	Semi standard non polar	33892256
Limocitrol,2TBDMS,isomer #6	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O	3823.4	Semi standard non polar	33892256
Limocitrol,3TBDMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3949.5	Semi standard non polar	33892256
Limocitrol,3TBDMS,isomer #2	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3955.4	Semi standard non polar	33892256
Limocitrol,3TBDMS,isomer #3	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3994.1	Semi standard non polar	33892256
Limocitrol,3TBDMS,isomer #4	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O	3869.3	Semi standard non polar	33892256
Limocitrol,4TBDMS,isomer #1	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	4001.1	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 - Limocitrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0209000000-93f1fb58bcbe798bdc96	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Limocitrol GC-MS (4 TMS) - 70eV, Positive	splash10-0kfw-1013039000-3b149966c5658ead50e6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Limocitrol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Limocitrol 10V, Positive-QTOF	splash10-004i-0009000000-180ad41b6dc71a65dc83	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 20V, Positive-QTOF	splash10-004i-0009000000-d75c79a9e262a578d16d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 40V, Positive-QTOF	splash10-0uk9-0928000000-d75b7c456786dc53a93b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 10V, Negative-QTOF	splash10-004i-0009000000-1b16d8fb831c88f1d0db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 20V, Negative-QTOF	splash10-004i-0009000000-93c2a5b876f381b4a2b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 40V, Negative-QTOF	splash10-00di-7897000000-76477852f976c540e094	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 10V, Negative-QTOF	splash10-004i-0009000000-4389f520d5a46c87493e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 20V, Negative-QTOF	splash10-004i-0049000000-afeaeab71782110cadb3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 40V, Negative-QTOF	splash10-00dj-1933000000-7171f0fd02ad113c20cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 10V, Positive-QTOF	splash10-004i-0009000000-b6992d0ca4afb85cf2cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 20V, Positive-QTOF	splash10-004i-0009000000-93cf5a585ebab75d4c92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Limocitrol 40V, Positive-QTOF	splash10-0400-2395000000-f7925751adbf9dcd99b6	2021-09-22	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

FDB016819

KNApSAcK ID

C00004792

Chemspider ID

10228270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12311234

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1863251

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 Limocitrol (HMDB0037691)

MOL for HMDB0037691 (Limocitrol)

3D MOL for HMDB0037691 (Limocitrol)

3D SDF for HMDB0037691 (Limocitrol)

3D-SDF for HMDB0037691 (Limocitrol)

PDB for HMDB0037691 (Limocitrol)

3D PDB for HMDB0037691 (Limocitrol)

SMILES for HMDB0037691 (Limocitrol)

INCHI for HMDB0037691 (Limocitrol)

Structure for HMDB0037691 (Limocitrol)

3D Structure for HMDB0037691 (Limocitrol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra