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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:54 UTC

Update Date

2022-03-07 02:52:37 UTC

HMDB ID

HMDB0030605

Secondary Accession Numbers

HMDB30605

Metabolite Identification

Common Name

1,5-Dihydroxy-3-methoxy-2-prenylxanthone

Description

1,5-Dihydroxy-3-methoxy-2-prenylxanthone belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Based on a literature review very few articles have been published on 1,5-Dihydroxy-3-methoxy-2-prenylxanthone.

Structure

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

HMDB0030605
     RDKit          3D
1,5-Dihydroxy-3-methoxy-2-prenylxanthone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.9520   -1.5829   -2.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -0.9939   -1.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014   -0.7096   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3186   -1.0089   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4829   -0.7373   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6670   -1.0162   -0.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -0.7599   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9892   -1.0710   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0981   -1.6460   -2.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270   -0.7880   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1106   -0.2129    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992    0.0956    1.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -0.1807    0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    0.1171    1.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516    0.6465    2.6655 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730   -0.1618    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1241    0.1431    1.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402    0.7121    2.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.1253    0.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831    0.1796    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9841    1.3917    0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1330    1.4563    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5997    2.7849   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187    0.3209   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3402   -2.5195   -2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319   -0.8818   -3.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -1.8949   -2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.4600   -2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3279   -1.8920   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0994   -1.0216   -0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0403    0.0061    1.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8214    0.5475    2.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6930    0.9706    3.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -0.7385    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333    0.1837    2.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911    2.3142    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0363    3.5797    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6866    2.9324   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498    2.8604   -1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -0.6669   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8438    0.3672    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5608    0.4600   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 19  3  1  0
 16  5  2  0
 13  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 18 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
M  END


  Mrv0541 05061305232D          

 24 26  0  0  0  0            999 V2000
    5.7158    0.0000    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  1  0  0  0  0
 19 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20 13  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  2  0  0  0  0
 23  3  1  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030605

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O5/c1-10(2)7-8-11-14(23-3)9-15-16(17(11)21)18(22)12-5-4-6-13(20)19(12)24-15/h4-7,9,20-21H,8H2,1-3H3

> <INCHI_KEY>
INFMYEMPDJIILH-UHFFFAOYSA-N

> <FORMULA>
C19H18O5

> <MOLECULAR_WEIGHT>
326.3432

> <EXACT_MASS>
326.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.795130528045874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.573405310666668

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.373428416125005

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.868214090884659

> <JCHEM_PKA_STRONGEST_BASIC>
-4.283316645849507

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
91.48409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.05e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030605
     RDKit          3D
1,5-Dihydroxy-3-methoxy-2-prenylxanthone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.9520   -1.5829   -2.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -0.9939   -1.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014   -0.7096   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3186   -1.0089   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4829   -0.7373   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6670   -1.0162   -0.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -0.7599   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9892   -1.0710   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0981   -1.6460   -2.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270   -0.7880   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1106   -0.2129    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992    0.0956    1.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -0.1807    0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    0.1171    1.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516    0.6465    2.6655 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730   -0.1618    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1241    0.1431    1.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402    0.7121    2.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.1253    0.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831    0.1796    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9841    1.3917    0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1330    1.4563    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5997    2.7849   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187    0.3209   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3402   -2.5195   -2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319   -0.8818   -3.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -1.8949   -2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.4600   -2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3279   -1.8920   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0994   -1.0216   -0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0403    0.0061    1.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8214    0.5475    2.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6930    0.9706    3.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -0.7385    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333    0.1837    2.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911    2.3142    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0363    3.5797    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6866    2.9324   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498    2.8604   -1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -0.6669   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8438    0.3672    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5608    0.4600   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 19  3  1  0
 16  5  2  0
 13  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 18 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  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      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   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       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   23                                                            
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4   13                                                       
CONECT    7    8   10                                                       
CONECT    8    7   11                                                       
CONECT    9   14   15                                                       
CONECT   10    1    2    7                                                  
CONECT   11    8   14   17                                                  
CONECT   12    5   18   19                                                  
CONECT   13    6   19   20                                                  
CONECT   14    9   11   23                                                  
CONECT   15    9   16   24                                                  
CONECT   16   15   17   18                                                  
CONECT   17   11   16   21                                                  
CONECT   18   12   16   22                                                  
CONECT   19   12   13   24                                                  
CONECT   20   13                                                            
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23    3   14                                                       
CONECT   24   15   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0030605
HETATM    1  C1  UNL     1      -1.952  -1.583  -2.550  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.044  -0.994  -1.272  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.901  -0.710  -0.560  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.319  -1.009  -1.114  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.483  -0.737  -0.429  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.667  -1.016  -0.941  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.769  -0.760  -0.293  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.989  -1.071  -0.872  1.00  0.00           C  
HETATM    9  O3  UNL     1       5.098  -1.646  -2.116  1.00  0.00           O  
HETATM   10  C7  UNL     1       6.127  -0.788  -0.163  1.00  0.00           C  
HETATM   11  C8  UNL     1       6.111  -0.213   1.089  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.899   0.096   1.663  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.733  -0.181   0.967  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.503   0.117   1.516  1.00  0.00           C  
HETATM   15  O4  UNL     1       2.452   0.647   2.665  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.373  -0.162   0.817  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.124   0.143   1.381  1.00  0.00           C  
HETATM   18  O5  UNL     1       0.140   0.712   2.619  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.046  -0.125   0.702  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.383   0.180   1.252  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.984   1.392   0.671  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.133   1.456   0.022  1.00  0.00           C  
HETATM   23  C18 UNL     1      -4.600   2.785  -0.508  1.00  0.00           C  
HETATM   24  C19 UNL     1      -5.019   0.321  -0.229  1.00  0.00           C  
HETATM   25  H1  UNL     1      -1.340  -2.520  -2.511  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.532  -0.882  -3.317  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.983  -1.895  -2.881  1.00  0.00           H  
HETATM   28  H4  UNL     1       0.417  -1.460  -2.090  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.328  -1.892  -2.717  1.00  0.00           H  
HETATM   30  H6  UNL     1       7.099  -1.022  -0.593  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.040   0.006   1.639  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.821   0.548   2.641  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.693   0.971   3.101  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.009  -0.739   1.025  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.333   0.184   2.353  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.391   2.314   0.810  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.036   3.580   0.017  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.687   2.932  -0.298  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.450   2.860  -1.597  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.572  -0.667  -0.269  1.00  0.00           H  
HETATM   41  H17 UNL     1      -5.844   0.367   0.541  1.00  0.00           H  
HETATM   42  H18 UNL     1      -5.561   0.460  -1.206  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   28
CONECT    5    6   16   16
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   11   30
CONECT   11   12   31
CONECT   12   13   13   32
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   19   19
CONECT   18   33
CONECT   19   20
CONECT   20   21   34   35
CONECT   21   22   22   36
CONECT   22   23   24
CONECT   23   37   38   39
CONECT   24   40   41   42
END

HMDB0030605
     RDKit          3D
1,5-Dihydroxy-3-methoxy-2-prenylxanthone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.9520   -1.5829   -2.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -0.9939   -1.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014   -0.7096   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3186   -1.0089   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4829   -0.7373   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6670   -1.0162   -0.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -0.7599   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9892   -1.0710   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0981   -1.6460   -2.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1270   -0.7880   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1106   -0.2129    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992    0.0956    1.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -0.1807    0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5026    0.1171    1.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516    0.6465    2.6655 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730   -0.1618    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1241    0.1431    1.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402    0.7121    2.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456   -0.1253    0.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831    0.1796    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9841    1.3917    0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1330    1.4563    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5997    2.7849   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0187    0.3209   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3402   -2.5195   -2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319   -0.8818   -3.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -1.8949   -2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.4600   -2.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3279   -1.8920   -2.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0994   -1.0216   -0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0403    0.0061    1.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8214    0.5475    2.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6930    0.9706    3.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -0.7385    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333    0.1837    2.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911    2.3142    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0363    3.5797    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6866    2.9324   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498    2.8604   -1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -0.6669   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8438    0.3672    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5608    0.4600   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 19  3  1  0
 16  5  2  0
 13  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 18 33  1  0
 20 34  1  0
 20 35  1  0
 21 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₈O₅

Average Molecular Weight

326.3432

Monoisotopic Molecular Weight

326.115423686

IUPAC Name

1,5-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

1,5-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one

CAS Registry Number

77741-56-1

SMILES

COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=CC=C1

InChI Identifier

InChI=1S/C19H18O5/c1-10(2)7-8-11-14(23-3)9-15-16(17(11)21)18(22)12-5-4-6-13(20)19(12)24-15/h4-7,9,20-21H,8H2,1-3H3

InChI Key

INFMYEMPDJIILH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2-prenylated xanthones

Alternative Parents

Substituents

2-prenylated xanthone
Chromone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030605)

Cellular substructure

Membrane (HMDB: HMDB0030605)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030605)

Source

Endogenous

Endogenous (HMDB: HMDB0030605)

Plant

Plant (HMDB: HMDB0030605)

Exogenous

Food

Food (HMDB: HMDB0030605)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	242 - 244 °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	0.03 g/L	ALOGPS
logP	3.79	ALOGPS
logP	4.57	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.48 m³·mol⁻¹	ChemAxon
Polarizability	34.8 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]+	178.016	31661259
DarkChem	[M-H]-	177.377	31661259
DeepCCS	[M+H]+	181.678	30932474
DeepCCS	[M-H]-	179.32	30932474
DeepCCS	[M-2H]-	213.497	30932474
DeepCCS	[M+Na]+	189.164	30932474
AllCCS	[M+H]+	176.4	32859911
AllCCS	[M+H-H2O]+	173.0	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	177.9	32859911
AllCCS	[M+HCOO]-	177.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,5-Dihydroxy-3-methoxy-2-prenylxanthone	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=CC=C1	4248.5	Standard polar	33892256
1,5-Dihydroxy-3-methoxy-2-prenylxanthone	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=CC=C1	2963.6	Standard non polar	33892256
1,5-Dihydroxy-3-methoxy-2-prenylxanthone	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=CC=C1	2967.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,5-Dihydroxy-3-methoxy-2-prenylxanthone,1TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1CC=C(C)C)C(=O)C1=CC=CC(O)=C1O2	3042.0	Semi standard non polar	33892256
1,5-Dihydroxy-3-methoxy-2-prenylxanthone,1TMS,isomer #2	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1O2	3038.3	Semi standard non polar	33892256
1,5-Dihydroxy-3-methoxy-2-prenylxanthone,2TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1CC=C(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1O2	3005.8	Semi standard non polar	33892256
1,5-Dihydroxy-3-methoxy-2-prenylxanthone,1TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C)C(=O)C1=CC=CC(O)=C1O2	3266.1	Semi standard non polar	33892256
1,5-Dihydroxy-3-methoxy-2-prenylxanthone,1TBDMS,isomer #2	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O2	3253.8	Semi standard non polar	33892256
1,5-Dihydroxy-3-methoxy-2-prenylxanthone,2TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O2	3437.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-1092000000-4a90ba9faf405e5b7cce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-2043900000-cae0da46564b54b2c671	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-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 - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 10V, Positive-QTOF	splash10-004i-0039000000-23fa8ec2765cb01dbbd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 20V, Positive-QTOF	splash10-00vi-3096000000-26adac22483a3fac5662	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 40V, Positive-QTOF	splash10-014i-9480000000-5f8f0a6eabbc4dec852b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 10V, Negative-QTOF	splash10-004i-0009000000-e31be23dd6e30892242f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 20V, Negative-QTOF	splash10-004i-0039000000-79281fa9a1496ceae9d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 40V, Negative-QTOF	splash10-05tu-5971000000-47cc2359ab686ba268be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 10V, Negative-QTOF	splash10-004i-0009000000-9e96b9c23c7cae4a8238	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 20V, Negative-QTOF	splash10-004i-0039000000-bad6a3e83fa915f0b2ec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 40V, Negative-QTOF	splash10-00di-2694000000-bf0e360bc3180fdbb5c6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 10V, Positive-QTOF	splash10-00b9-0069000000-e26be828c8ae624d0162	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 20V, Positive-QTOF	splash10-00di-0090000000-e8092f6c1b3ae61af7c0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-3-methoxy-2-prenylxanthone 40V, Positive-QTOF	splash10-00kf-0190000000-e4d22357d1c1848bbd8d	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

FDB002499

KNApSAcK ID

Not Available

Chemspider ID

8624460

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10449043

PDB ID

Not Available

ChEBI ID

790787

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 1,5-Dihydroxy-3-methoxy-2-prenylxanthone (HMDB0030605)

MOL for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

3D MOL for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

3D SDF for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

3D-SDF for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

PDB for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

3D PDB for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

SMILES for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

INCHI for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

Structure for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

3D Structure for HMDB0030605 (1,5-Dihydroxy-3-methoxy-2-prenylxanthone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra