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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:55 UTC

Update Date

2022-03-07 02:52:37 UTC

HMDB ID

HMDB0030606

Secondary Accession Numbers

HMDB30606

Metabolite Identification

Common Name

1,7-Dihydroxy-3-methoxy-2-prenylxanthone

Description

1,7-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 1,7-Dihydroxy-3-methoxy-2-prenylxanthone.

Structure

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

HMDB0030606
     RDKit          3D
1,7-Dihydroxy-3-methoxy-2-prenylxanthone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.7568   -3.1810   -1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -1.9991   -0.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910   -1.2044   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -1.5521   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -0.8014    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7372   -1.1888   -0.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809   -0.4937    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0707   -0.9126   -0.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1513   -0.1611    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373    1.0140    1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9909    1.7904    1.4316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6547    1.4234    1.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574    0.6764    0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902    1.1191    1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719    2.1762    1.8194 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    0.3493    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0895    0.7305    1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213    1.9302    1.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1424   -0.0317    0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5243    0.4005    0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1391    1.0380   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483    0.6929   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7277    1.4326   -2.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -0.4176   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9978   -3.1120   -2.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -3.9735   -0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7174   -3.4606   -1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -2.4628   -0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150   -1.8319   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.4754    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8499    2.6473    1.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4362    2.3448    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811    2.3626    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497   -0.4818    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5183    1.0699    1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.8908   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0674    0.6582   -2.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5298    2.1675   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8941    1.9671   -2.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250   -0.7811   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7151   -0.0663    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4933   -1.2930   -0.0476 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
  9 10  2  0
 10 11  1  0
 10 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
  8 29  1  0
  9 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


  Mrv1652309272007472D          

 24 26  0  0  0  0            999 V2000
 9999.6888 9999.5072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.828710000.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1184 9999.5072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.547810000.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.261610000.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.975310000.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.691010000.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9753 9999.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.547810001.9825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.261610001.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.683710001.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.969310001.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.969310000.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.683710000.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.258310001.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.543810001.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.543810000.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.258210000.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.832410001.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.832410000.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.121410001.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.406910001.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.406910000.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.121310000.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 11 12  1  0  0  0  0
 12 15  2  0  0  0  0
 18 13  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 19 21  2  0  0  0  0
 24 20  2  0  0  0  0
 14 23  1  0  0  0  0
 11 22  1  0  0  0  0
 24  3  1  0  0  0  0
 20  4  1  0  0  0  0
 19  9  1  0  0  0  0
 17  2  1  0  0  0  0
  1 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030606

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=CC(O)=CC=C1O2

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

> <INCHI_KEY>
JKOMBLYQDHTFJC-UHFFFAOYSA-N

> <FORMULA>
C19H18O5

> <MOLECULAR_WEIGHT>
326.3432

> <EXACT_MASS>
326.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.977808811494086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,7-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
4.573405310666668

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.158204870675855

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.103052899957726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.727845731729198

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
91.48409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,7-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030606
     RDKit          3D
1,7-Dihydroxy-3-methoxy-2-prenylxanthone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.7568   -3.1810   -1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -1.9991   -0.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910   -1.2044   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -1.5521   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -0.8014    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7372   -1.1888   -0.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809   -0.4937    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0707   -0.9126   -0.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1513   -0.1611    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373    1.0140    1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9909    1.7904    1.4316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6547    1.4234    1.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574    0.6764    0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902    1.1191    1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719    2.1762    1.8194 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    0.3493    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0895    0.7305    1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213    1.9302    1.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1424   -0.0317    0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5243    0.4005    0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1391    1.0380   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483    0.6929   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7277    1.4326   -2.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -0.4176   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9978   -3.1120   -2.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -3.9735   -0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7174   -3.4606   -1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -2.4628   -0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150   -1.8319   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.4754    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8499    2.6473    1.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4362    2.3448    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811    2.3626    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497   -0.4818    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5183    1.0699    1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.8908   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0674    0.6582   -2.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5298    2.1675   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8941    1.9671   -2.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250   -0.7811   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7151   -0.0663    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4933   -1.2930   -0.0476 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
  9 10  2  0
 10 11  1  0
 10 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
  8 29  1  0
  9 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                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.0868665.747   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8660.7478667.287   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8668.7548665.747   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8671.4238667.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8672.7558668.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.0878667.287   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8675.4238668.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8674.0878665.747   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8671.4238670.367   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8672.7558669.595   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8666.0768670.367   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8664.7438669.597   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.7438668.057   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.0768667.287   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.4168670.366   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.0828669.596   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.0828668.056   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.4158667.286   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.0878669.597   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.0878668.057   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.7608670.366   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.4268669.597   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.4268668.057   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.7608667.287   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   17                                                            
CONECT    3   24                                                            
CONECT    4    5   20                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10   19                                                       
CONECT   10    9                                                            
CONECT   11   12   22                                                       
CONECT   12   13   11   15                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   23    1                                                  
CONECT   15   16   12                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    2                                                  
CONECT   18   17   13                                                       
CONECT   19   20   21    9                                                  
CONECT   20   19   24    4                                                  
CONECT   21   22   19                                                       
CONECT   22   21   23   11                                                  
CONECT   23   22   24   14                                                  
CONECT   24   23   20    3                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0030606
HETATM    1  C1  UNL     1      -1.757  -3.181  -1.290  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.942  -1.999  -0.578  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.891  -1.204  -0.128  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.418  -1.552  -0.373  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.512  -0.801   0.049  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.737  -1.189  -0.220  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.781  -0.494   0.166  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.071  -0.913  -0.126  1.00  0.00           C  
HETATM    9  C7  UNL     1       6.151  -0.161   0.290  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.937   1.014   1.001  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.991   1.790   1.432  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.655   1.423   1.287  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.557   0.676   0.875  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.290   1.119   1.179  1.00  0.00           C  
HETATM   15  O4  UNL     1       2.072   2.176   1.819  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.230   0.349   0.749  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.090   0.731   1.014  1.00  0.00           C  
HETATM   18  O5  UNL     1      -0.221   1.930   1.743  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.142  -0.032   0.584  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.524   0.400   0.876  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.139   1.038  -0.326  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.248   0.693  -0.903  1.00  0.00           C  
HETATM   23  C18 UNL     1      -4.728   1.433  -2.102  1.00  0.00           C  
HETATM   24  C19 UNL     1      -5.075  -0.418  -0.384  1.00  0.00           C  
HETATM   25  H1  UNL     1      -0.998  -3.112  -2.067  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.462  -3.973  -0.552  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.717  -3.461  -1.762  1.00  0.00           H  
HETATM   28  H4  UNL     1       0.597  -2.463  -0.925  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.215  -1.832  -0.680  1.00  0.00           H  
HETATM   30  H6  UNL     1       7.185  -0.475   0.069  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.850   2.647   1.948  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.436   2.345   1.846  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.081   2.363   1.955  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.150  -0.482   1.205  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.518   1.070   1.745  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.577   1.891  -0.754  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.067   0.658  -2.837  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.530   2.168  -1.863  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.894   1.967  -2.623  1.00  0.00           H  
HETATM   40  H16 UNL     1      -5.725  -0.781  -1.228  1.00  0.00           H  
HETATM   41  H17 UNL     1      -5.715  -0.066   0.462  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.493  -1.293  -0.048  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   29
CONECT    9   10   10   30
CONECT   10   11   12
CONECT   11   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

HMDB0030606
     RDKit          3D
1,7-Dihydroxy-3-methoxy-2-prenylxanthone
 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.7568   -3.1810   -1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -1.9991   -0.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910   -1.2044   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -1.5521   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -0.8014    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7372   -1.1888   -0.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7809   -0.4937    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0707   -0.9126   -0.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1513   -0.1611    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373    1.0140    1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9909    1.7904    1.4316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6547    1.4234    1.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574    0.6764    0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902    1.1191    1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719    2.1762    1.8194 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    0.3493    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0895    0.7305    1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213    1.9302    1.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1424   -0.0317    0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5243    0.4005    0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1391    1.0380   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483    0.6929   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7277    1.4326   -2.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -0.4176   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9978   -3.1120   -2.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -3.9735   -0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7174   -3.4606   -1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -2.4628   -0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150   -1.8319   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.4754    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8499    2.6473    1.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4362    2.3448    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811    2.3626    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497   -0.4818    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5183    1.0699    1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.8908   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0674    0.6582   -2.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5298    2.1675   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8941    1.9671   -2.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250   -0.7811   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7151   -0.0663    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4933   -1.2930   -0.0476 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
  9 10  2  0
 10 11  1  0
 10 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
  8 29  1  0
  9 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

Value	Source
1,7-Dihydroxy-3-methoxy-2-(3-methyl-2-buten-1-yl)-9H-xanthen-9-one	PhytoBank
1,7-Dihydroxy-3-methoxy-2-(3-methylbut-2-enyl)xanthen-9-one	PhytoBank

Chemical Formula

C₁₉H₁₈O₅

Average Molecular Weight

326.3432

Monoisotopic Molecular Weight

326.115423686

IUPAC Name

1,7-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

1,7-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one

CAS Registry Number

77741-58-3

SMILES

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

InChI Identifier

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

InChI Key

JKOMBLYQDHTFJC-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: HMDB0030606)

Cellular substructure

Membrane (HMDB: HMDB0030606)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030606)

Source

Endogenous

Endogenous (HMDB: HMDB0030606)

Plant

Plant (HMDB: HMDB0030606)

Exogenous

Food

Food (HMDB: HMDB0030606)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	220 - 222 °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	3.87	ALOGPS
logP	4.57	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.1	ChemAxon
pKa (Strongest Basic)	-3.7	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	34.98 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]+	179.673	31661259
DarkChem	[M-H]-	176.442	31661259
DeepCCS	[M+H]+	186.316	30932474
DeepCCS	[M-H]-	183.92	30932474
DeepCCS	[M-2H]-	218.28	30932474
DeepCCS	[M+Na]+	194.011	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
1,7-Dihydroxy-3-methoxy-2-prenylxanthone	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C=CC(O)=C1	4336.8	Standard polar	33892256
1,7-Dihydroxy-3-methoxy-2-prenylxanthone	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C=CC(O)=C1	3014.2	Standard non polar	33892256
1,7-Dihydroxy-3-methoxy-2-prenylxanthone	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C=CC(O)=C1	3098.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,7-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(O)=CC=C1O2	3069.8	Semi standard non polar	33892256
1,7-Dihydroxy-3-methoxy-2-prenylxanthone,1TMS,isomer #2	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=CC(O[Si](C)(C)C)=CC=C1O2	3105.1	Semi standard non polar	33892256
1,7-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(O[Si](C)(C)C)=CC=C1O2	3070.3	Semi standard non polar	33892256
1,7-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(O)=CC=C1O2	3292.5	Semi standard non polar	33892256
1,7-Dihydroxy-3-methoxy-2-prenylxanthone,1TBDMS,isomer #2	COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O2	3306.0	Semi standard non polar	33892256
1,7-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(O[Si](C)(C)C(C)(C)C)=CC=C1O2	3514.0	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 - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-1094000000-69843e264f64f9f8e93c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone GC-MS (2 TMS) - 70eV, Positive	splash10-0a6r-5034900000-60e69148d27503f2dd65	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,7-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 - 1,7-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 - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 10V, Positive-QTOF	splash10-004i-0039000000-7289392ced24974b8967	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 20V, Positive-QTOF	splash10-00vi-3096000000-50be3504d016bf35fab9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 40V, Positive-QTOF	splash10-014r-7490000000-1d4e9dea5adb5bb89368	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 10V, Negative-QTOF	splash10-004i-0009000000-3742ce35146ed5a09205	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 20V, Negative-QTOF	splash10-004i-0039000000-62db0631f713092cc423	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 40V, Negative-QTOF	splash10-052r-4961000000-2850d9ffad2e00bf4595	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 10V, Positive-QTOF	splash10-00b9-0069000000-cfe979e6aa25fb01695f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 20V, Positive-QTOF	splash10-00di-0090000000-0c01b3aff5f7dc49c9e8	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 40V, Positive-QTOF	splash10-0006-0190000000-413b0ccad37651fd78a8	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 10V, Negative-QTOF	splash10-004i-0009000000-9e96b9c23c7cae4a8238	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 20V, Negative-QTOF	splash10-004i-0039000000-0d3fa1c0a944d1c7a285	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,7-Dihydroxy-3-methoxy-2-prenylxanthone 40V, Negative-QTOF	splash10-00r6-1293000000-53b524132390354c053c	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

FDB002500

KNApSAcK ID

Not Available

Chemspider ID

444610

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

509269

PDB ID

Not Available

ChEBI ID

545146

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 1,7-Dihydroxy-3-methoxy-2-prenylxanthone (HMDB0030606)

MOL for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

3D MOL for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

3D SDF for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

3D-SDF for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

PDB for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

3D PDB for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

SMILES for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

INCHI for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

Structure for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

3D Structure for HMDB0030606 (1,7-Dihydroxy-3-methoxy-2-prenylxanthone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra