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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:40:19 UTC

Update Date

2022-03-07 02:55:19 UTC

HMDB ID

HMDB0037424

Secondary Accession Numbers

HMDB37424

Metabolite Identification

Common Name

Citrusinol

Description

Citrusinol belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Thus, citrusinol is considered to be a flavonoid lipid molecule. Citrusinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Citrusinol has been detected, but not quantified in, citrus. This could make citrusinol a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 02241209272D          

 26 29  0  0  0  0            999 V2000
   -2.0942   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    2.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781    1.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219   -1.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -1.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911   -2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    2.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  2  0  0  0  0
  4 26  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 22  1  0  0  0  0
  8  9  1  0  0  0  0
  8 25  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 25  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 26  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

HMDB0037424
     RDKit          3D
Citrusinol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -4.7639   -1.4146    1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441   -0.1220    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.9184    2.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6328   -0.4561    1.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4903   -0.3193    1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186    0.1915   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193    0.5198   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6926    0.9985   -1.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    1.1641   -2.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532    1.6435   -3.9956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114    0.8230   -2.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891    0.9526   -2.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882    1.3819   -3.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0558    0.5808   -2.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396    0.7258   -2.7404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.1065   -0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.2854   -0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -0.2524   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5443   -0.6614    0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3205   -1.1171    1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3395   -1.5312    2.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -1.1596    2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -0.7579    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099    0.0112   -0.2321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    0.3375   -0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106    0.3650   -0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -1.6421    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -2.2052    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6309   -1.3015    0.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221    0.4665    3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5167    1.2867    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9715    1.7547    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164   -0.8389    2.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -0.5704    1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6283    1.2590   -2.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9752    1.8605   -4.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217    1.0703   -3.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7123    0.0915   -1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585   -0.6201    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8232   -0.9262    3.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8496   -1.5251    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615   -0.8030    1.6517 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
  7 26  1  0
 26  2  1  0
 25  6  1  0
 25 11  2  0
 23 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
 10 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
M  END


  Mrv0541 02241209272D          

 26 29  0  0  0  0            999 V2000
   -2.0942   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    2.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781    1.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -1.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219   -1.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -1.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911   -2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    2.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3805    1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  2  0  0  0  0
  4 26  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 22  1  0  0  0  0
  8  9  1  0  0  0  0
  8 25  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 25  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 26  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037424

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O6/c1-20(2)8-7-12-14(26-20)9-13(22)15-16(23)17(24)18(25-19(12)15)10-3-5-11(21)6-4-10/h3-9,21-22,24H,1-2H3

> <INCHI_KEY>
OKQQXHUICMLKQI-UHFFFAOYSA-N

> <FORMULA>
C20H16O6

> <MOLECULAR_WEIGHT>
352.3374

> <EXACT_MASS>
352.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.27937931376662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.664053509333333

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.908543481974354

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.182073578210199

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8210109326513466

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
97.29379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citrusinol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037424
     RDKit          3D
Citrusinol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -4.7639   -1.4146    1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441   -0.1220    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.9184    2.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6328   -0.4561    1.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4903   -0.3193    1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186    0.1915   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193    0.5198   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6926    0.9985   -1.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    1.1641   -2.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532    1.6435   -3.9956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114    0.8230   -2.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891    0.9526   -2.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882    1.3819   -3.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0558    0.5808   -2.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396    0.7258   -2.7404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.1065   -0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.2854   -0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -0.2524   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5443   -0.6614    0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3205   -1.1171    1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3395   -1.5312    2.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -1.1596    2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -0.7579    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099    0.0112   -0.2321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    0.3375   -0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106    0.3650   -0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -1.6421    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -2.2052    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6309   -1.3015    0.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221    0.4665    3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5167    1.2867    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9715    1.7547    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164   -0.8389    2.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -0.5704    1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6283    1.2590   -2.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9752    1.8605   -4.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217    1.0703   -3.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7123    0.0915   -1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585   -0.6201    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8232   -0.9262    3.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8496   -1.5251    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615   -0.8030    1.6517 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
  7 26  1  0
 26  2  1  0
 25  6  1  0
 25 11  2  0
 23 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
 10 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.909  -3.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.577  -2.357   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.577  -0.817   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.909  -0.047   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.909   1.492   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.092   3.803   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.092   2.263   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.424   1.492   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.759   2.263   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.091  -3.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.426  -2.357   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.426  -0.817   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.091  -0.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.759  -0.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.759  -2.357   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.761  -3.128   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.761  -2.088   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.244  -2.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.770  -3.803   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.577   3.803   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.577   2.263   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.242   1.492   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.242  -0.047   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.092  -0.817   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.424  -0.047   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.244  -0.817   0.000  0.00  0.00           O+0
CONECT    1    2   18                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4   21                                                       
CONECT    6    7                                                            
CONECT    7    6    8   22                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8                                                            
CONECT   10   11   15                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   10   14                                                       
CONECT   16   11                                                            
CONECT   17   18                                                            
CONECT   18    1   17   19   26                                             
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21    5   20   22                                                  
CONECT   22    7   21   23                                                  
CONECT   23    3   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25    8   14   24                                                  
CONECT   26    4   18                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0037424
HETATM    1  C1  UNL     1      -4.764  -1.415   1.279  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.944  -0.122   1.304  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.676   0.918   2.163  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.633  -0.456   1.869  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.490  -0.319   1.220  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.519   0.192  -0.134  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.719   0.520  -0.711  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.693   0.998  -1.993  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.503   1.164  -2.730  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.553   1.644  -3.996  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.311   0.823  -2.117  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.889   0.953  -2.761  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.988   1.382  -3.930  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.056   0.581  -2.060  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.240   0.726  -2.740  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.021   0.107  -0.787  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.186  -0.285  -0.032  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.480  -0.252  -0.441  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.544  -0.661   0.384  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.321  -1.117   1.654  1.00  0.00           C  
HETATM   21  O4  UNL     1       6.340  -1.531   2.505  1.00  0.00           O  
HETATM   22  C18 UNL     1       4.017  -1.160   2.091  1.00  0.00           C  
HETATM   23  C19 UNL     1       2.984  -0.758   1.277  1.00  0.00           C  
HETATM   24  O5  UNL     1       0.810   0.011  -0.232  1.00  0.00           O  
HETATM   25  C20 UNL     1      -0.301   0.337  -0.826  1.00  0.00           C  
HETATM   26  O6  UNL     1      -3.911   0.365  -0.002  1.00  0.00           O  
HETATM   27  H1  UNL     1      -5.122  -1.642   2.300  1.00  0.00           H  
HETATM   28  H2  UNL     1      -4.057  -2.205   0.909  1.00  0.00           H  
HETATM   29  H3  UNL     1      -5.631  -1.302   0.588  1.00  0.00           H  
HETATM   30  H4  UNL     1      -5.022   0.467   3.114  1.00  0.00           H  
HETATM   31  H5  UNL     1      -5.517   1.287   1.535  1.00  0.00           H  
HETATM   32  H6  UNL     1      -3.972   1.755   2.298  1.00  0.00           H  
HETATM   33  H7  UNL     1      -2.616  -0.839   2.885  1.00  0.00           H  
HETATM   34  H8  UNL     1      -0.546  -0.570   1.655  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.628   1.259  -2.455  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.975   1.861  -4.718  1.00  0.00           H  
HETATM   37  H11 UNL     1       3.322   1.070  -3.679  1.00  0.00           H  
HETATM   38  H12 UNL     1       4.712   0.092  -1.415  1.00  0.00           H  
HETATM   39  H13 UNL     1       6.558  -0.620   0.022  1.00  0.00           H  
HETATM   40  H14 UNL     1       6.823  -0.926   3.138  1.00  0.00           H  
HETATM   41  H15 UNL     1       3.850  -1.525   3.107  1.00  0.00           H  
HETATM   42  H16 UNL     1       1.962  -0.803   1.652  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    4   26
CONECT    3   30   31   32
CONECT    4    5    5   33
CONECT    5    6   34
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   35
CONECT    9   10   11
CONECT   10   36
CONECT   11   12   25   25
CONECT   12   13   13   14
CONECT   14   15   16   16
CONECT   15   37
CONECT   16   17   24
CONECT   17   18   18   23
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   20   21   22
CONECT   21   40
CONECT   22   23   23   41
CONECT   23   42
CONECT   24   25
END

HMDB0037424
     RDKit          3D
Citrusinol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -4.7639   -1.4146    1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441   -0.1220    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.9184    2.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6328   -0.4561    1.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4903   -0.3193    1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186    0.1915   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193    0.5198   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6926    0.9985   -1.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    1.1641   -2.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532    1.6435   -3.9956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114    0.8230   -2.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891    0.9526   -2.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9882    1.3819   -3.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0558    0.5808   -2.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396    0.7258   -2.7404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.1065   -0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.2854   -0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -0.2524   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5443   -0.6614    0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3205   -1.1171    1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3395   -1.5312    2.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -1.1596    2.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -0.7579    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099    0.0112   -0.2321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    0.3375   -0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106    0.3650   -0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -1.6421    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -2.2052    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6309   -1.3015    0.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221    0.4665    3.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5167    1.2867    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9715    1.7547    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6164   -0.8389    2.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -0.5704    1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6283    1.2590   -2.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9752    1.8605   -4.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217    1.0703   -3.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7123    0.0915   -1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585   -0.6201    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8232   -0.9262    3.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8496   -1.5251    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9615   -0.8030    1.6517 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
  7 26  1  0
 26  2  1  0
 25  6  1  0
 25 11  2  0
 23 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
 10 36  1  0
 15 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5-Dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₆O₆

Average Molecular Weight

352.3374

Monoisotopic Molecular Weight

352.094688244

IUPAC Name

3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one

Traditional Name

citrusinol

CAS Registry Number

112516-43-5

SMILES

CC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H16O6/c1-20(2)8-7-12-14(26-20)9-13(22)15-16(23)17(24)18(25-19(12)15)10-3-5-11(21)6-4-10/h3-9,21-22,24H,1-2H3

InChI Key

OKQQXHUICMLKQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111994 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	252 - 254 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	3.48	ALOGPS
logP	3.66	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.29 m³·mol⁻¹	ChemAxon
Polarizability	36.28 Å³	ChemAxon
Number of Rings	4	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]+	186.373	30932474
DeepCCS	[M-H]-	184.015	30932474
DeepCCS	[M-2H]-	218.155	30932474
DeepCCS	[M+Na]+	193.384	30932474
AllCCS	[M+H]+	184.2	32859911
AllCCS	[M+H-H2O]+	180.8	32859911
AllCCS	[M+NH4]+	187.3	32859911
AllCCS	[M+Na]+	188.2	32859911
AllCCS	[M-H]-	183.2	32859911
AllCCS	[M+Na-2H]-	182.5	32859911
AllCCS	[M+HCOO]-	182.0	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.	7.5 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3643 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2931.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	270.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	667.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	694.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1236.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	483.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1364.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	320.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	187.6 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	39.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citrusinol	CC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C1	4338.5	Standard polar	33892256
Citrusinol	CC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C1	3197.9	Standard non polar	33892256
Citrusinol	CC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C1	3468.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citrusinol,1TMS,isomer #1	CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O)C=C2)=C(O)C3=O)O1	3390.3	Semi standard non polar	33892256
Citrusinol,1TMS,isomer #2	CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O)C=C2)=C(O[Si](C)(C)C)C3=O)O1	3318.6	Semi standard non polar	33892256
Citrusinol,1TMS,isomer #3	CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2)=C(O)C3=O)O1	3385.6	Semi standard non polar	33892256
Citrusinol,2TMS,isomer #1	CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O)C=C2)=C(O[Si](C)(C)C)C3=O)O1	3257.2	Semi standard non polar	33892256
Citrusinol,2TMS,isomer #2	CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2)=C(O)C3=O)O1	3344.0	Semi standard non polar	33892256
Citrusinol,2TMS,isomer #3	CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2)=C(O[Si](C)(C)C)C3=O)O1	3215.5	Semi standard non polar	33892256
Citrusinol,3TMS,isomer #1	CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2)=C(O[Si](C)(C)C)C3=O)O1	3245.3	Semi standard non polar	33892256
Citrusinol,1TBDMS,isomer #1	CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O)C=C2)=C(O)C3=O)O1	3635.4	Semi standard non polar	33892256
Citrusinol,1TBDMS,isomer #2	CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O)C=C2)=C(O[Si](C)(C)C(C)(C)C)C3=O)O1	3572.5	Semi standard non polar	33892256
Citrusinol,1TBDMS,isomer #3	CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O)C3=O)O1	3619.9	Semi standard non polar	33892256
Citrusinol,2TBDMS,isomer #1	CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O)C=C2)=C(O[Si](C)(C)C(C)(C)C)C3=O)O1	3781.2	Semi standard non polar	33892256
Citrusinol,2TBDMS,isomer #2	CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O)C3=O)O1	3874.7	Semi standard non polar	33892256
Citrusinol,2TBDMS,isomer #3	CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O[Si](C)(C)C(C)(C)C)C3=O)O1	3763.3	Semi standard non polar	33892256
Citrusinol,3TBDMS,isomer #1	CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O[Si](C)(C)C(C)(C)C)C3=O)O1	3984.0	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 - Citrusinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0359000000-3b303a6db852fa491011	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusinol GC-MS (3 TMS) - 70eV, Positive	splash10-0ufv-2370970000-01e0aa43d08cc24571cb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citrusinol 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 - Citrusinol 10V, Positive-QTOF	splash10-0udi-0019000000-a75d185b8170caae15a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 20V, Positive-QTOF	splash10-0udi-1039000000-d08aaa3a0718be1eb0ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 40V, Positive-QTOF	splash10-014j-5490000000-9da76c4acd5a5d826cb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 10V, Negative-QTOF	splash10-0udi-0009000000-76e922ed8787cdc2a2e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 20V, Negative-QTOF	splash10-0udi-0039000000-2c5fecbc31b4246a6af1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 40V, Negative-QTOF	splash10-00lr-0791000000-61e2eb4c21b7824f6e77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 10V, Negative-QTOF	splash10-0udi-0009000000-4d16a6676fb6a009705b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 20V, Negative-QTOF	splash10-0udi-0049000000-8937570b885d0085f32c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 40V, Negative-QTOF	splash10-0gi3-4794000000-deabc5d2a258c26baf44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 10V, Positive-QTOF	splash10-0udi-0009000000-2baef9d2edd9c62c0a8d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 20V, Positive-QTOF	splash10-0udi-0009000000-9faf695343b343b32b17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citrusinol 40V, Positive-QTOF	splash10-014i-2094000000-798a386c358654811268	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016472

KNApSAcK ID

C00005077

Chemspider ID

24691934

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44259051

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Citrusinol → 6-(4-{3,5-dihydroxy-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Citrusinol → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-3-yl]oxy}oxane-2-carboxylic acid	details
Citrusinol → 3,4,5-trihydroxy-6-{[3-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-5-yl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Citrusinol → (4-{3,5-dihydroxy-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-2-yl}phenyl)oxidanesulfonic acid	details

Showing metabocard for Citrusinol (HMDB0037424)

MOL for HMDB0037424 (Citrusinol)

3D MOL for HMDB0037424 (Citrusinol)

3D SDF for HMDB0037424 (Citrusinol)

3D-SDF for HMDB0037424 (Citrusinol)

PDB for HMDB0037424 (Citrusinol)

3D PDB for HMDB0037424 (Citrusinol)

SMILES for HMDB0037424 (Citrusinol)

INCHI for HMDB0037424 (Citrusinol)

Structure for HMDB0037424 (Citrusinol)

3D Structure for HMDB0037424 (Citrusinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions