Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:53:03 UTC

Update Date

2022-03-07 02:56:34 UTC

HMDB ID

HMDB0040354

Secondary Accession Numbers

HMDB40354

Metabolite Identification

Common Name

1,4,5-Trihydroxy-3-prenylxanthone

Description

1,4,5-Trihydroxy-3-prenylxanthone belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. 1,4,5-Trihydroxy-3-prenylxanthone has been detected, but not quantified in, fruits. This could make 1,4,5-trihydroxy-3-prenylxanthone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,4,5-Trihydroxy-3-prenylxanthone.

Structure

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

HMDB0040354
     RDKit          3D
1,4,5-Trihydroxy-3-prenylxanthone
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.6319   -0.8596    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340    0.1286   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404    1.4111    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5435   -0.1524   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965    0.7910   -1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103    0.1385   -0.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0816   -1.1506   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283   -1.7223    0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127   -3.0116    0.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.9998   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -1.5376    0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6278   -2.7147    0.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340   -0.7120    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8914   -1.2073    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0358   -0.4546    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9009    0.8310   -0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730    1.3735   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5093    2.6467   -0.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5274    0.5795   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    1.0329   -0.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2664    0.3042   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    0.8713   -0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    2.1760   -1.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -1.7775    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9871   -1.0954   -0.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449   -0.3809    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5467    2.2810    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    1.4544    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6706    1.4892    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -1.0821   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.6361   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101    1.0876   -2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.7040   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5521   -3.6374    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483   -2.2171    0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0251   -0.8684    0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7622    1.4678   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6139    3.0106   -1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565    2.5742   -1.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  6  1  0
 21 10  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  9 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 23 39  1  0
M  END

  Mrv0541 05061311472D          

 23 25  0  0  0  0            999 V2000
    0.0000   -2.4750    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
    5.7158    0.8250    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
    5.7158    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
    0.7145   -0.4125    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   -1.6500    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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    0.0000    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
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 13  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23 17  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040354

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=CC(O)=C2C(=O)C3=C(OC2=C1O)C(O)=CC=C3

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-9(2)6-7-10-8-13(20)14-16(22)11-4-3-5-12(19)17(11)23-18(14)15(10)21/h3-6,8,19-21H,7H2,1-2H3

> <INCHI_KEY>
BRVVGOBMRRGKCK-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.3166

> <EXACT_MASS>
312.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.866069560922654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4,5-trihydroxy-3-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
4.427511254666667

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.41055964836087

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.702230357164384

> <JCHEM_PKA_STRONGEST_BASIC>
-4.399901632716092

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
87.00179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4,5-trihydroxy-3-(3-methylbut-2-en-1-yl)xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040354
     RDKit          3D
1,4,5-Trihydroxy-3-prenylxanthone
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.6319   -0.8596    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340    0.1286   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404    1.4111    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5435   -0.1524   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965    0.7910   -1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103    0.1385   -0.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0816   -1.1506   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283   -1.7223    0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127   -3.0116    0.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.9998   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -1.5376    0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6278   -2.7147    0.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340   -0.7120    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8914   -1.2073    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0358   -0.4546    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9009    0.8310   -0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730    1.3735   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5093    2.6467   -0.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5274    0.5795   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    1.0329   -0.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2664    0.3042   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    0.8713   -0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    2.1760   -1.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -1.7775    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9871   -1.0954   -0.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449   -0.3809    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5467    2.2810    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    1.4544    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6706    1.4892    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -1.0821   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.6361   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101    1.0876   -2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.7040   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5521   -3.6374    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483   -2.2171    0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0251   -0.8684    0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7622    1.4678   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6139    3.0106   -1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565    2.5742   -1.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  6  1  0
 21 10  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  9 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 23 39  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       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    4    5                                                       
CONECT    4    3   11                                                       
CONECT    5    3   12                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8   10   13                                                       
CONECT    9    1    2    6                                                  
CONECT   10    7    8   15                                                  
CONECT   11    4   16   17                                                  
CONECT   12    5   17   19                                                  
CONECT   13    8   14   20                                                  
CONECT   14   13   16   18                                                  
CONECT   15   10   18   21                                                  
CONECT   16   11   14   22                                                  
CONECT   17   11   12   23                                                  
CONECT   18   14   15   23                                                  
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0040354
HETATM    1  C1  UNL     1       5.632  -0.860   0.131  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.534   0.129  -0.021  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.540   1.411   0.738  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.543  -0.152  -0.848  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.396   0.791  -1.060  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.110   0.139  -0.684  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.082  -1.151  -0.219  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.128  -1.722   0.119  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.213  -3.012   0.590  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.303  -1.000  -0.010  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.531  -1.538   0.318  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.628  -2.715   0.750  1.00  0.00           O  
HETATM   13  C11 UNL     1      -3.634  -0.712   0.144  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.891  -1.207   0.460  1.00  0.00           C  
HETATM   15  C13 UNL     1      -6.036  -0.455   0.317  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.901   0.831  -0.159  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.673   1.374  -0.489  1.00  0.00           C  
HETATM   18  O3  UNL     1      -4.509   2.647  -0.963  1.00  0.00           O  
HETATM   19  C16 UNL     1      -3.527   0.580  -0.331  1.00  0.00           C  
HETATM   20  O4  UNL     1      -2.345   1.033  -0.623  1.00  0.00           O  
HETATM   21  C17 UNL     1      -1.266   0.304  -0.481  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.055   0.871  -0.818  1.00  0.00           C  
HETATM   23  O5  UNL     1      -0.041   2.176  -1.287  1.00  0.00           O  
HETATM   24  H1  UNL     1       5.259  -1.777   0.653  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.987  -1.095  -0.905  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.445  -0.381   0.732  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.547   2.281   0.054  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.445   1.454   1.366  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.671   1.489   1.421  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.550  -1.082  -1.391  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.547   1.636  -0.358  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.310   1.088  -2.111  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.024  -1.704  -0.125  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.552  -3.637   0.730  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.948  -2.217   0.828  1.00  0.00           H  
HETATM   36  H13 UNL     1      -7.025  -0.868   0.574  1.00  0.00           H  
HETATM   37  H14 UNL     1      -6.762   1.468  -0.292  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.614   3.011  -1.192  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.857   2.574  -1.529  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4    4
CONECT    3   27   28   29
CONECT    4    5   30
CONECT    5    6   31   32
CONECT    6    7    7   22
CONECT    7    8   33
CONECT    8    9   10   10
CONECT    9   34
CONECT   10   11   21
CONECT   11   12   12   13
CONECT   13   14   14   19
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   37
CONECT   17   18   19   19
CONECT   18   38
CONECT   19   20
CONECT   20   21
CONECT   21   22   22
CONECT   22   23
CONECT   23   39
END

HMDB0040354
     RDKit          3D
1,4,5-Trihydroxy-3-prenylxanthone
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.6319   -0.8596    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340    0.1286   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404    1.4111    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5435   -0.1524   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965    0.7910   -1.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103    0.1385   -0.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0816   -1.1506   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283   -1.7223    0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127   -3.0116    0.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.9998   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312   -1.5376    0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6278   -2.7147    0.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340   -0.7120    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8914   -1.2073    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0358   -0.4546    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9009    0.8310   -0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730    1.3735   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5093    2.6467   -0.9628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5274    0.5795   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    1.0329   -0.6235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2664    0.3042   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    0.8713   -0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    2.1760   -1.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -1.7775    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9871   -1.0954   -0.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4449   -0.3809    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5467    2.2810    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    1.4544    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6706    1.4892    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -1.0821   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.6361   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101    1.0876   -2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.7040   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5521   -3.6374    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483   -2.2171    0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0251   -0.8684    0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7622    1.4678   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6139    3.0106   -1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565    2.5742   -1.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  6  1  0
 21 10  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  9 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4,5-Trihydroxy-3-(3-methyl-2-butenyl)-9H-xanthen-9-one, 9ci	HMDB

Chemical Formula

C₁₈H₁₆O₅

Average Molecular Weight

312.3166

Monoisotopic Molecular Weight

312.099773622

IUPAC Name

1,4,5-trihydroxy-3-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

1,4,5-trihydroxy-3-(3-methylbut-2-en-1-yl)xanthen-9-one

CAS Registry Number

136364-72-2

SMILES

CC(C)=CCC1=CC(O)=C2C(=O)C3=C(OC2=C1O)C(O)=CC=C3

InChI Identifier

InChI=1S/C18H16O5/c1-9(2)6-7-10-8-13(20)14-16(22)11-4-3-5-12(19)17(11)23-18(14)15(10)21/h3-6,8,19-21H,7H2,1-2H3

InChI Key

BRVVGOBMRRGKCK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Prenylbenzoquinol
Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040354)
Cell membrane (HMDB: HMDB0040354)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040354)

Source

Exogenous

Exogenous (HMDB: HMDB0040354)

Food

Food (HMDB: HMDB0040354)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040354)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040354)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	185 - 186 °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	0.05 g/L	ALOGPS
logP	3.42	ALOGPS
logP	4.43	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.7	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87 m³·mol⁻¹	ChemAxon
Polarizability	32.87 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
DarkChem	[M+H]+	175.372	31661259
DarkChem	[M-H]-	173.797	31661259
DeepCCS	[M+H]+	169.213	30932474
DeepCCS	[M-H]-	166.855	30932474
DeepCCS	[M-2H]-	200.821	30932474
DeepCCS	[M+Na]+	176.508	30932474
AllCCS	[M+H]+	173.1	32859911
AllCCS	[M+H-H2O]+	169.5	32859911
AllCCS	[M+NH4]+	176.4	32859911
AllCCS	[M+Na]+	177.3	32859911
AllCCS	[M-H]-	173.2	32859911
AllCCS	[M+Na-2H]-	172.5	32859911
AllCCS	[M+HCOO]-	171.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4,5-Trihydroxy-3-prenylxanthone	CC(C)=CCC1=CC(O)=C2C(=O)C3=C(OC2=C1O)C(O)=CC=C3	4346.1	Standard polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone	CC(C)=CCC1=CC(O)=C2C(=O)C3=C(OC2=C1O)C(O)=CC=C3	2778.9	Standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone	CC(C)=CCC1=CC(O)=C2C(=O)C3=C(OC2=C1O)C(O)=CC=C3	2902.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,4,5-Trihydroxy-3-prenylxanthone,1TMS,isomer #1	CC(C)=CCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=CC(O)=C3OC2=C1O	3133.3	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,1TMS,isomer #2	CC(C)=CCC1=CC(O)=C2C(=O)C3=CC=CC(O)=C3OC2=C1O[Si](C)(C)C	3080.3	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,1TMS,isomer #3	CC(C)=CCC1=CC(O)=C2C(=O)C3=CC=CC(O[Si](C)(C)C)=C3OC2=C1O	3116.5	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,2TMS,isomer #1	CC(C)=CCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=CC(O[Si](C)(C)C)=C3OC2=C1O	3062.9	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,2TMS,isomer #2	CC(C)=CCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=CC(O)=C3OC2=C1O[Si](C)(C)C	3046.7	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,2TMS,isomer #3	CC(C)=CCC1=CC(O)=C2C(=O)C3=CC=CC(O[Si](C)(C)C)=C3OC2=C1O[Si](C)(C)C	2997.4	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,3TMS,isomer #1	CC(C)=CCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=CC(O[Si](C)(C)C)=C3OC2=C1O[Si](C)(C)C	3050.0	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,1TBDMS,isomer #1	CC(C)=CCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=CC(O)=C3OC2=C1O	3361.8	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,1TBDMS,isomer #2	CC(C)=CCC1=CC(O)=C2C(=O)C3=CC=CC(O)=C3OC2=C1O[Si](C)(C)C(C)(C)C	3314.5	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,1TBDMS,isomer #3	CC(C)=CCC1=CC(O)=C2C(=O)C3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3OC2=C1O	3346.0	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,2TBDMS,isomer #1	CC(C)=CCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3OC2=C1O	3535.7	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,2TBDMS,isomer #2	CC(C)=CCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=CC(O)=C3OC2=C1O[Si](C)(C)C(C)(C)C	3550.6	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,2TBDMS,isomer #3	CC(C)=CCC1=CC(O)=C2C(=O)C3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3OC2=C1O[Si](C)(C)C(C)(C)C	3473.4	Semi standard non polar	33892256
1,4,5-Trihydroxy-3-prenylxanthone,3TBDMS,isomer #1	CC(C)=CCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=CC(O[Si](C)(C)C(C)(C)C)=C3OC2=C1O[Si](C)(C)C(C)(C)C	3710.9	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 - 1,4,5-Trihydroxy-3-prenylxanthone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2090000000-3f35101f924661aa14df	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone GC-MS (3 TMS) - 70eV, Positive	splash10-03di-2102690000-82249fc53bcf6ad7e02c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 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 - 1,4,5-Trihydroxy-3-prenylxanthone 10V, Positive-QTOF	splash10-03di-0049000000-0f1756f093e355cc07f1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 20V, Positive-QTOF	splash10-0a4i-5092000000-e532fb236bd1e4ee36e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 40V, Positive-QTOF	splash10-052r-9410000000-86c3d602b53bde7dbad9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 10V, Negative-QTOF	splash10-03di-0009000000-c755f8aff099223bf970	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 20V, Negative-QTOF	splash10-03di-0029000000-9b8e89d3f948b7c690c3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 40V, Negative-QTOF	splash10-0a4r-3930000000-c3f993ef2daf77bbc2b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 10V, Positive-QTOF	splash10-03di-0039000000-967c66db00050282103b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 20V, Positive-QTOF	splash10-0ab9-0091000000-5f9561b2f5d0c1aadd08	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 40V, Positive-QTOF	splash10-056u-1190000000-81a1ac4e344bf5e2c9cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 10V, Negative-QTOF	splash10-03di-0009000000-a968dea78994eb63447d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 20V, Negative-QTOF	splash10-03di-0049000000-461dcdcaa86ee90fccad	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Trihydroxy-3-prenylxanthone 40V, Negative-QTOF	splash10-08i0-1970000000-a0dadeae5cc5a360e974	2021-09-25	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

FDB020080

KNApSAcK ID

C00057863

Chemspider ID

23252000

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15127377

PDB ID

Not Available

ChEBI ID

174994

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 1,4,5-Trihydroxy-3-prenylxanthone (HMDB0040354)

MOL for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

3D MOL for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

3D SDF for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

3D-SDF for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

PDB for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

3D PDB for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

SMILES for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

INCHI for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

Structure for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

3D Structure for HMDB0040354 (1,4,5-Trihydroxy-3-prenylxanthone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra