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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:45:10 UTC

Update Date

2022-03-07 02:56:10 UTC

HMDB ID

HMDB0039334

Secondary Accession Numbers

HMDB39334

Metabolite Identification

Common Name

Citrusin D

Description

Citrusin D belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Based on a literature review a small amount of articles have been published on Citrusin D.

Structure

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

HMDB0039334
     RDKit          3D
Citrusin D
 46 47  0  0  0  0  0  0  0  0999 V2000
    6.4942    0.8790   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0091   -0.4462   -0.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -0.6297   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857    0.4119   -0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3925    0.2672   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6469    1.4826   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4985    1.6644   -1.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120    0.6604   -2.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    0.5170   -1.4325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    0.2246   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644    1.2942    0.5791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242    1.3429    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528    1.4061   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4420    1.4534   -0.6089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9875    0.2191    1.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0813    0.6486    2.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -1.0539    1.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1213   -2.1141    0.9267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1542   -1.0841    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -2.0276    0.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -1.0207   -0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -2.1102   -0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712   -1.9221   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0076   -3.0199   -0.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5761    0.8203    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9336    1.4276    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3578    1.3587   -1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2025    1.4188   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.4091   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    2.6976   -1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.2273   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498    1.2023   -3.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4434    0.1724    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    2.3099    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7637    2.3214   -1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    0.5386   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046    1.8500   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0463    0.0610    0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8655   -0.0787    3.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978   -1.3104    2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0389   -2.3570   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378   -1.4933   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501   -2.9422    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -1.2305   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -3.0931   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974   -2.8986   -0.1579 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 19 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
M  END


  Mrv0541 05061311012D          

 24 25  0  0  0  0            999 V2000
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    8.5737    0.8250    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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 10  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22  1  1  0  0  0  0
 22 11  1  0  0  0  0
 23  6  1  0  0  0  0
 23 16  1  0  0  0  0
 24 12  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039334

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C/COC2OC(CO)C(O)C(O)C2O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O8/c1-22-11-7-9(4-5-10(11)18)3-2-6-23-16-15(21)14(20)13(19)12(8-17)24-16/h2-5,7,12-21H,6,8H2,1H3/b3-2-

> <INCHI_KEY>
JOIDTHZGWZZGMU-IHWYPQMZSA-N

> <FORMULA>
C16H22O8

> <MOLECULAR_WEIGHT>
342.3411

> <EXACT_MASS>
342.13146768

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
33.68386971667628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.4162605109999996

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.212794853443203

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.974780462369008

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835511361624

> <JCHEM_POLAR_SURFACE_AREA>
128.84

> <JCHEM_REFRACTIVITY>
84.04990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039334
     RDKit          3D
Citrusin D
 46 47  0  0  0  0  0  0  0  0999 V2000
    6.4942    0.8790   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0091   -0.4462   -0.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -0.6297   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857    0.4119   -0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3925    0.2672   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6469    1.4826   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4985    1.6644   -1.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120    0.6604   -2.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    0.5170   -1.4325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    0.2246   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644    1.2942    0.5791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242    1.3429    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528    1.4061   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4420    1.4534   -0.6089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9875    0.2191    1.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0813    0.6486    2.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -1.0539    1.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1213   -2.1141    0.9267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1542   -1.0841    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -2.0276    0.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -1.0207   -0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -2.1102   -0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712   -1.9221   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0076   -3.0199   -0.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5761    0.8203    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9336    1.4276    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3578    1.3587   -1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2025    1.4188   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.4091   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    2.6976   -1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.2273   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498    1.2023   -3.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4434    0.1724    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    2.3099    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7637    2.3214   -1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    0.5386   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046    1.8500   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0463    0.0610    0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8655   -0.0787    3.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978   -1.3104    2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0389   -2.3570   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378   -1.4933   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501   -2.9422    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -1.2305   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -3.0931   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974   -2.8986   -0.1579 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 19 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  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       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.338   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      16.004   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    3    6                                                       
CONECT    3    2    9                                                       
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    2   23                                                       
CONECT    7    9   11                                                       
CONECT    8   12   17                                                       
CONECT    9    3    4    7                                                  
CONECT   10    5   11   18                                                  
CONECT   11    7   10   22                                                  
CONECT   12    8   13   24                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   23   24                                                  
CONECT   17    8                                                            
CONECT   18   10                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22    1   11                                                       
CONECT   23    6   16                                                       
CONECT   24   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0039334
HETATM    1  C1  UNL     1       6.494   0.879  -0.207  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.009  -0.446  -0.235  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.640  -0.630  -0.432  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.786   0.412  -0.594  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.392   0.267  -0.796  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.647   1.483  -0.878  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.498   1.664  -1.409  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.312   0.660  -2.069  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.522   0.517  -1.432  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.480   0.225  -0.091  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.064   1.294   0.579  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.424   1.343   0.552  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.053   1.406  -0.812  1.00  0.00           C  
HETATM   14  O4  UNL     1      -5.442   1.453  -0.609  1.00  0.00           O  
HETATM   15  C11 UNL     1      -3.987   0.219   1.351  1.00  0.00           C  
HETATM   16  O5  UNL     1      -4.081   0.649   2.689  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.231  -1.054   1.218  1.00  0.00           C  
HETATM   18  O6  UNL     1      -4.121  -2.114   0.927  1.00  0.00           O  
HETATM   19  C13 UNL     1      -2.154  -1.084   0.198  1.00  0.00           C  
HETATM   20  O7  UNL     1      -1.196  -2.028   0.634  1.00  0.00           O  
HETATM   21  C14 UNL     1       1.955  -1.021  -0.817  1.00  0.00           C  
HETATM   22  C15 UNL     1       2.826  -2.110  -0.652  1.00  0.00           C  
HETATM   23  C16 UNL     1       4.171  -1.922  -0.460  1.00  0.00           C  
HETATM   24  O8  UNL     1       5.008  -3.020  -0.300  1.00  0.00           O  
HETATM   25  H1  UNL     1       7.576   0.820   0.039  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.934   1.428   0.592  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.358   1.359  -1.202  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.203   1.419  -0.567  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.107   2.409  -0.410  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.064   2.698  -1.366  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.177  -0.227  -2.382  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.650   1.202  -3.085  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.443   0.172   0.286  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.712   2.310   1.059  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.764   2.321  -1.367  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.848   0.539  -1.452  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.905   1.850  -1.384  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.046   0.061   0.992  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.866  -0.079   3.325  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.798  -1.310   2.217  1.00  0.00           H  
HETATM   41  H17 UNL     1      -4.039  -2.357  -0.044  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.538  -1.493  -0.757  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.450  -2.942   0.365  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.906  -1.231  -0.911  1.00  0.00           H  
HETATM   45  H21 UNL     1       2.379  -3.093  -0.686  1.00  0.00           H  
HETATM   46  H22 UNL     1       5.997  -2.899  -0.158  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   28
CONECT    5    6   21   21
CONECT    6    7    7   29
CONECT    7    8   30
CONECT    8    9   31   32
CONECT    9   10
CONECT   10   11   19   33
CONECT   11   12
CONECT   12   13   15   34
CONECT   13   14   35   36
CONECT   14   37
CONECT   15   16   17   38
CONECT   16   39
CONECT   17   18   19   40
CONECT   18   41
CONECT   19   20   42
CONECT   20   43
CONECT   21   22   44
CONECT   22   23   23   45
CONECT   23   24
CONECT   24   46
END

HMDB0039334
     RDKit          3D
Citrusin D
 46 47  0  0  0  0  0  0  0  0999 V2000
    6.4942    0.8790   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0091   -0.4462   -0.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -0.6297   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857    0.4119   -0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3925    0.2672   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6469    1.4826   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4985    1.6644   -1.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120    0.6604   -2.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222    0.5170   -1.4325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    0.2246   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644    1.2942    0.5791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242    1.3429    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528    1.4061   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4420    1.4534   -0.6089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9875    0.2191    1.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0813    0.6486    2.6891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -1.0539    1.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1213   -2.1141    0.9267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1542   -1.0841    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -2.0276    0.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547   -1.0207   -0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -2.1102   -0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712   -1.9221   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0076   -3.0199   -0.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5761    0.8203    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9336    1.4276    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3578    1.3587   -1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2025    1.4188   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.4091   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    2.6976   -1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.2273   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498    1.2023   -3.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4434    0.1724    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    2.3099    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7637    2.3214   -1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    0.5386   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046    1.8500   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0463    0.0610    0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8655   -0.0787    3.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978   -1.3104    2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0389   -2.3570   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378   -1.4933   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501   -2.9422    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -1.2305   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -3.0931   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974   -2.8986   -0.1579 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 19 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Isoconiferin	HMDB

Chemical Formula

C₁₆H₂₂O₈

Average Molecular Weight

342.3411

Monoisotopic Molecular Weight

342.13146768

IUPAC Name

2-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

65995-51-9

SMILES

COC1=C(O)C=CC(\C=C/COC2OC(CO)C(O)C(O)C2O)=C1

InChI Identifier

InChI=1S/C16H22O8/c1-22-11-7-9(4-5-10(11)18)3-2-6-23-16-15(21)14(20)13(19)12(8-17)24-16/h2-5,7,12-21H,6,8H2,1H3/b3-2-

InChI Key

JOIDTHZGWZZGMU-IHWYPQMZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Organoheterocyclic compound
Ether
Acetal
Oxacycle
Polyol
Primary alcohol
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0039334)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039334)

Source

Endogenous

Endogenous (HMDB: HMDB0039334)

Plant

Plant (HMDB: HMDB0039334)

Animal

Animal (HMDB: HMDB0039334)

Exogenous

Food

Food (HMDB: HMDB0039334)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0039334)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039334)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039334)

Lipid metabolism pathway (HMDB: HMDB0039334)

Biochemical process

Lipid transport (HMDB: HMDB0039334)

Role

Biological role

Energy source (HMDB: HMDB0039334)

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	26450 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	4.11 g/L	ALOGPS
logP	-0.44	ALOGPS
logP	-0.42	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.97	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	128.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.05 m³·mol⁻¹	ChemAxon
Polarizability	33.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	181.55	31661259
DarkChem	[M-H]-	178.785	31661259
DeepCCS	[M+H]+	184.675	30932474
DeepCCS	[M-H]-	182.317	30932474
DeepCCS	[M-2H]-	216.062	30932474
DeepCCS	[M+Na]+	191.786	30932474
AllCCS	[M+H]+	182.3	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	185.1	32859911
AllCCS	[M+Na]+	185.9	32859911
AllCCS	[M-H]-	178.2	32859911
AllCCS	[M+Na-2H]-	178.5	32859911
AllCCS	[M+HCOO]-	178.9	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.	3.02 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1463 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.18 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	117.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1506.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	202.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	92.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	298.6 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	321.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	262.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	693.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	284.5 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	903.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	213.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	412.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	278.1 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	65.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citrusin D	COC1=C(O)C=CC(\C=C/COC2OC(CO)C(O)C(O)C2O)=C1	4843.6	Standard polar	33892256
Citrusin D	COC1=C(O)C=CC(\C=C/COC2OC(CO)C(O)C(O)C2O)=C1	3117.9	Standard non polar	33892256
Citrusin D	COC1=C(O)C=CC(\C=C/COC2OC(CO)C(O)C(O)C2O)=C1	3055.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citrusin D,1TMS,isomer #1	COC1=CC(/C=C\COC2OC(CO)C(O)C(O)C2O)=CC=C1O[Si](C)(C)C	3180.8	Semi standard non polar	33892256
Citrusin D,1TMS,isomer #2	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O)C(O)C2O)=CC=C1O	3128.0	Semi standard non polar	33892256
Citrusin D,1TMS,isomer #3	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C)C(O)C2O)=CC=C1O	3109.9	Semi standard non polar	33892256
Citrusin D,1TMS,isomer #4	COC1=CC(/C=C\COC2OC(CO)C(O)C(O[Si](C)(C)C)C2O)=CC=C1O	3106.7	Semi standard non polar	33892256
Citrusin D,1TMS,isomer #5	COC1=CC(/C=C\COC2OC(CO)C(O)C(O)C2O[Si](C)(C)C)=CC=C1O	3114.5	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #1	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O)C(O)C2O)=CC=C1O[Si](C)(C)C	3114.9	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #10	COC1=CC(/C=C\COC2OC(CO)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O	3085.1	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #2	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C)C(O)C2O)=CC=C1O[Si](C)(C)C	3095.1	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #3	COC1=CC(/C=C\COC2OC(CO)C(O)C(O[Si](C)(C)C)C2O)=CC=C1O[Si](C)(C)C	3105.4	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #4	COC1=CC(/C=C\COC2OC(CO)C(O)C(O)C2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3095.6	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #5	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O)=CC=C1O	3089.2	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #6	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O)=CC=C1O	3087.1	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #7	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O)C(O)C2O[Si](C)(C)C)=CC=C1O	3090.8	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #8	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)=CC=C1O	3061.2	Semi standard non polar	33892256
Citrusin D,2TMS,isomer #9	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)=CC=C1O	3074.2	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #1	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O)=CC=C1O[Si](C)(C)C	3062.0	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #10	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O	3033.7	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #2	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O)=CC=C1O[Si](C)(C)C	3048.9	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #3	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O)C(O)C2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3065.3	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #4	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)=CC=C1O[Si](C)(C)C	3038.2	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #5	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3059.1	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #6	COC1=CC(/C=C\COC2OC(CO)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3060.4	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #7	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)=CC=C1O	3041.6	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #8	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)=CC=C1O	3078.5	Semi standard non polar	33892256
Citrusin D,3TMS,isomer #9	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O	3043.9	Semi standard non polar	33892256
Citrusin D,4TMS,isomer #1	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)=CC=C1O[Si](C)(C)C	3052.5	Semi standard non polar	33892256
Citrusin D,4TMS,isomer #2	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3083.5	Semi standard non polar	33892256
Citrusin D,4TMS,isomer #3	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3043.5	Semi standard non polar	33892256
Citrusin D,4TMS,isomer #4	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3039.5	Semi standard non polar	33892256
Citrusin D,4TMS,isomer #5	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O	3069.4	Semi standard non polar	33892256
Citrusin D,5TMS,isomer #1	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3107.7	Semi standard non polar	33892256
Citrusin D,1TBDMS,isomer #1	COC1=CC(/C=C\COC2OC(CO)C(O)C(O)C2O)=CC=C1O[Si](C)(C)C(C)(C)C	3444.3	Semi standard non polar	33892256
Citrusin D,1TBDMS,isomer #2	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O)=CC=C1O	3402.1	Semi standard non polar	33892256
Citrusin D,1TBDMS,isomer #3	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)=CC=C1O	3399.7	Semi standard non polar	33892256
Citrusin D,1TBDMS,isomer #4	COC1=CC(/C=C\COC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O	3383.9	Semi standard non polar	33892256
Citrusin D,1TBDMS,isomer #5	COC1=CC(/C=C\COC2OC(CO)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3399.7	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #1	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O)=CC=C1O[Si](C)(C)C(C)(C)C	3600.9	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #10	COC1=CC(/C=C\COC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3609.0	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #2	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)=CC=C1O[Si](C)(C)C(C)(C)C	3631.1	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #3	COC1=CC(/C=C\COC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O[Si](C)(C)C(C)(C)C	3612.8	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #4	COC1=CC(/C=C\COC2OC(CO)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3626.3	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #5	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)=CC=C1O	3590.2	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #6	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O	3572.0	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #7	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3590.4	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #8	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O	3591.7	Semi standard non polar	33892256
Citrusin D,2TBDMS,isomer #9	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3603.0	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #1	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)=CC=C1O[Si](C)(C)C(C)(C)C	3790.3	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #10	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3776.2	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #2	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O[Si](C)(C)C(C)(C)C	3781.4	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #3	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3785.8	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #4	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O[Si](C)(C)C(C)(C)C	3792.3	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #5	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3806.0	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #6	COC1=CC(/C=C\COC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3810.2	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #7	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O	3763.3	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #8	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3801.5	Semi standard non polar	33892256
Citrusin D,3TBDMS,isomer #9	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3758.3	Semi standard non polar	33892256
Citrusin D,4TBDMS,isomer #1	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O[Si](C)(C)C(C)(C)C	3974.7	Semi standard non polar	33892256
Citrusin D,4TBDMS,isomer #2	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4017.9	Semi standard non polar	33892256
Citrusin D,4TBDMS,isomer #3	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3974.1	Semi standard non polar	33892256
Citrusin D,4TBDMS,isomer #4	COC1=CC(/C=C\COC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3967.7	Semi standard non polar	33892256
Citrusin D,4TBDMS,isomer #5	COC1=CC(/C=C\COC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3988.2	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 - Citrusin D GC-MS (Non-derivatized) - 70eV, Positive	splash10-08mi-9444000000-6ce121f4cb1d78440737	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusin D GC-MS (4 TMS) - 70eV, Positive	splash10-014i-1273129000-808c80940f0463515d68	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusin D 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 - Citrusin D 10V, Positive-QTOF	splash10-01r6-0509000000-7fbb21ff4cd473fada66	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 20V, Positive-QTOF	splash10-03di-0901000000-62d999ef30a4e83f786f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 40V, Positive-QTOF	splash10-03di-4900000000-8337f01874e6630fd6ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 10V, Negative-QTOF	splash10-0006-2609000000-b4174d1f267ac9787bec	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 20V, Negative-QTOF	splash10-03mi-3902000000-56d6ba59a67781e52ebb	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 40V, Negative-QTOF	splash10-0a4l-9400000000-383e73410691bfc589e2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 10V, Positive-QTOF	splash10-03ed-0904000000-fff88ca50d82578dd807	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 20V, Positive-QTOF	splash10-000t-0910000000-2b20fad4f6098c6c1ff8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 40V, Positive-QTOF	splash10-075l-1920000000-e09af6846555ce2170cc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 10V, Negative-QTOF	splash10-0006-0119000000-d7aa4afecf13bd9a2c7b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 20V, Negative-QTOF	splash10-000i-4924000000-241bf4dd984ec93abbd8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusin D 40V, Negative-QTOF	splash10-000m-6596000000-6b2ee9d4289cdce59d76	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB018887

KNApSAcK ID

C00053975

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752609

PDB ID

Not Available

ChEBI ID

175342

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1876301

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 ]
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Showing metabocard for Citrusin D (HMDB0039334)

MOL for HMDB0039334 (Citrusin D)

3D MOL for HMDB0039334 (Citrusin D)

3D SDF for HMDB0039334 (Citrusin D)

3D-SDF for HMDB0039334 (Citrusin D)

PDB for HMDB0039334 (Citrusin D)

3D PDB for HMDB0039334 (Citrusin D)

SMILES for HMDB0039334 (Citrusin D)

INCHI for HMDB0039334 (Citrusin D)

Structure for HMDB0039334 (Citrusin D)

3D Structure for HMDB0039334 (Citrusin D)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra